Greenport, NY Vacation Rentals

Explore 173 vacation rentals, homes, and villas in Greenport, NY for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $115 per night and featuring up to 7 bedrooms and 11 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

173 Vacation Rentals in Greenport

Charming Greenport Gem 1, 1 Mile to Ferry!

Greenport, NY, US
2 Bedrooms 6 Guests
Sep 27 - 30
$242 night

Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire at this 2-bedroom, 1-bathroom vacation rental! Situated in the heart of Greenport, this apartment provides an updated interior, historic feel, a fully equipped kitchen, and a walkable location near town attractions. Take the ferry to Shelter Island and enjoy a day on Shell Beach. Explore Orient Beach State Park and grab a glass of wine at a vineyard on the way back. -- THE PROPERTY -- 2nd-Floor Apartment in Historic Home | Walk to Downtown Boutiques & Restaurants | Near Beaches Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play APARTMENT FEATURES: 3 flat-screen TVs w/ cable, dining table, laptop-friendly workspace, gardenKITCHEN: Stainless steel appliances, dishwasher, cooking basics & spices, Keurig coffee maker, blender, toaster, tea kettle knife set, dishware & flatwareGENERAL: Free WiFi, central A/C, linens & towels, central heating, complimentary toiletries, trash bags & paper towels, hair dryer, hangers, self check-inFAQ: Ring Doorbell device (facing front door entry), quiet hours (10:00 PM-8:00 AM), no porch access, addt'l rental on-site (separate unit & entrance)ACCESSIBILITY: Stairs required for access, entire 2nd-floor unitPARKING: Street parking (first-come, first-served), no driveway parkingADDT’L ACCOMMODATIONS: An additional 1-bedroom property for 4 guests is available on-site with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- THINGS TO SEE + DO: Antique Carousel (0.4 miles), East End Seaport Museum & Marine Foundation (0.7 miles), The Fire Fighter (0.7 miles), Ferry to Shelter Island (0.7 miles), Railroad Museum of Long Island (0.7 miles), Horton Point Lighthouse Nautical Museum (5.5 miles)OUTDOOR RECREATION: 67 Steps Beach (1.1 miles), Norman E. Klipp Marine Park (1.8 miles), Crescent Beach (2.7 miles, accessible by ferry), Truman’s Beach (4.0 miles), Mashomack Preserve (6.4 miles, accessible by ferry), Shell Beach (6.4 miles, accessible by ferry), Orient Beach State Park (10.4 miles)WINERIES + BREWERIES: Greenport Harbor Brewing Company (0.3 miles), One Woman Winery Greenport (0.4 miles), Kontokosta Winery (1.2 miles), The Old Field Vineyards (4.0 miles)AIRPORTS: Long Island Islip MacArthur Airport (44.0 miles), Laguardia Airport (90.9 miles), John F. Kennedy International Airport (91.9 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed- No events, parties or large gatherings- Additional fees and taxes may apply- Photo ID may be required upon check-in- NOTE: This apartment is an entire 2nd-floor unit of the building and requires stairs to access- NOTE: There is an additional rental unit on-site with a completely separate entrance - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed- NOTE: Please observe quiet hours between 10:00 PM to 8:00 AM- NOTE: The porch is not available for guest use

Brand New Build! Greenport Gem w/ Yard & Patio

Greenport, NY, US
3 Bedrooms 6 Guests
Sep 28 - Oct 1
$370 night

Peaceful Neighborhood | Centrally Located | Backyard Grill Outside Coastal charm and maritime history await at this welcoming vacation rental in Greenport, NY! Featuring all of the essential comforts, a fully equipped kitchen, and easy access to local hotspots, this cozy home promises an unforgettable family-friendly retreat. When adventure calls, sip local wines at one of the dozens of local wineries, or catch sunsets at 67 Steps Beach. Book your dates and start planning your getaway today. -- THE PROPERTY -- O26-134 OUTDOOR LIVING - Private backyard - Furnished deck - Patio area w/ outdoor dining area - Gas grill (connected to house propane tank) INDOOR LIVING - Smart TV - Dining table, breakfast bar - Board games, books KITCHEN - Stove/oven, refrigerator, dishwasher, microwave - Cooking basics, dishware/flatware - Espresso machine & French press (coffee provided) - Toaster, blender, ice maker, spices ACCESSIBILITY - Multi-level home, 8 steps to enter - All bedrooms & full bathrooms on upper & lower levels PARKING - Driveway (3 vehicles) - Free street parking (first-come, first-served) -- THE LOCATION -- - Centrally located in Greenport village, within walking distance of shops and the marina - 0.4 miles to Mitchell Park & Marina - Short walk to 67 Steps Beach - Less than 2 miles to Kontokosta Winery - 2 miles to Inlet Pond County Park - Quick ferry to Shelter Island - 10 miles to Peconic Water Sports Downtown Sag Harbor - Town is accessible from NYC via LIRR or the Jitney -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - Please ensure the yellow gas lever for the grill is returned to the horizontal position when not in use - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in Licence number: O26-134

Steps to Beach + Sunset Views! East Marion Home

East Marion, NY, US
3 Bedrooms 6 Guests
Oct 1 - 15
$218 night

Outdoor Shower | < 3 Mi to Eastern End of the North Fork Wine Trail Sandy shores, calm waters, and North Fork charm await at this recently renovated 3-bedroom, 2-bathroom vacation rental — just 700 feet from the beaches of Long Island Sound. This East Marion home offers walk-to-beach access, peaceful surroundings with mature trees, an outdoor entertainment space, and unforgettable sunset views that transform every evening into a coastal spectacle. Secure your dates today! -- THE PROPERTY -- After a day at the nearby beach, rinse off in the outdoor shower and enjoy dinner on the gas grill (propane provided), soaking in the vibrant colors over the Sound. Designed for families and couples, this North Fork beach house combines modern updates with comfortable coastal living, making it a perfect retreat for summer getaways or extended stays. With close proximity to local beaches, vineyards, farm stands, and charming North Fork towns, this vacation home delivers the ideal mix of location, comfort, and classic seaside charm — all just steps from the water. Inside, the house is bright, airy, and spacious, with plenty of windows and natural light. The kitchen boasts ample counter space for meal prep, while the cozy living room provides a comfortable space to unwind. With three bedrooms featuring lush bedding, there's plenty of room to spread out and relax after a day of beachcombing. With a range of modern amenities like central air, washer and dryer, WiFi, and more, this dog-friendly home provides everything you need for a relaxing and enjoyable stay in East Marion. Book your getaway today and experience the beauty and charm of the North Fork! -- THE LOCATION -- For outdoor enthusiasts, this area is a fisherman's paradise, offering local surfcasting and fishing charters in Orient Harbor and Greenport village. Explore nearby Montauk, Sag Harbor, and South Fork towns via picturesque ferries and a short drive across Shelter Island. Greenport, a charming seaside village on the North Fork, is just a short distance away, offering a rich history, farm-to-table cuisine, local wines, eclectic shops, and antique stores for a delightful afternoon of exploration. Additionally, enjoy easy access to Island's End Golf Course, Kontokosta Winery, local dining options, and the Village of Greenport. Wine connoisseurs will be delighted to explore over 60 vineyards on the North Fork Wine Trail all within 20 miles. Or try something local on tap at the Greenport Harbor Brewing tasting room, just 3 miles away. Notable nearby: 2 miles to Island's End golf Course 2.5 miles to Kontokosta Winery on the eastern end of the North Fork Wine Trail 2.5 miles to local Tiki Bar/Restaurant Billie's By The Bay, and fine indoor/outdoor dining at Porto Bello, both in Safe Harbor marinas on beautiful Stirling Basin 3 miles to the Village of Greenport 3 miles to Stony Brook Eastern Long Island Hospital 7 miles to Cross Sound Ferry at Orient Point (Access to New England year round and Block Island seasonally) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking anywhere on the premises - No pets allowed - Although we understand we love our pets like family, our next guests may not feel the same way, so we ask guests to keep their furry family members off the beds/furniture - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - Local regulations require a minimum stay of 14 days - Noise audible outside the property is prohibited between 10 PM and 8 AM ADDITIONAL INFORMATION - There are Smart TVs, so guests can stream all their subscribed streaming services - Propane is provided for the gas grill Licence number: 1208

Shelter Island Retreat w/ Outdoor Pool!

Shelter Island, NY, US
5 Bedrooms 8 Guests
Oct 8 - 11
$1,189 night

If you’re looking to escape bustling city life, book this 5-bedroom, 6.5-bath home in the Hamptons area! This Shelter Island vacation rental features an office and free WiFi, as well as amenities like a game room and pool to ensure a productive and restorative stay. With fun activities year-round, you can kayak on the nearby ocean, sip on some wine at the Wölffer Estate Vineyard, witness stunning views from Montauk Point, catch a Polo match, or get your holiday shopping done in the Hamptons! -- THE PROPERTY -- Seasonal Outdoor Pool | Fully Equipped Home Gym | Free WiFi (High Speed) | 110 Mi to NYC | 5,000 Sq Ft Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: 2 Twin Bunk Beds | Bedroom 5: Queen Bed | Bonus Room: King Bed OUTDOOR LIVING: Private beach w/ wood-burning fire pit & beach chairs, kayaks (available spring/summer months), near ocean, walk to beaches, deck, gas grill + outdoor kitchen area, outdoor fireplace, fire pit, bicycles, boating, beach chairs, beach umbrella, trampoline INDOOR LIVING: 3 Smart TVs w/ cable, en-suite bathrooms, walk-in closet, laptop-friendly workspace, game room w/ pool table, gas fireplaces, dining areas, jetted bathtub, shower, books KITCHEN: Refrigerator, stove/oven, blender, toaster, cooking basics GENERAL: Central A/C + heating, complimentary toiletries, linens/towels, washers/dryers, hair dryer, hangers, beach towels, trash bags/paper towels FAQ: Steps required for entry, bedroom + bathroom on 1st floor, zero-entrance shower PARKING: Driveway (7 vehicles) -- THE LOCATION -- THINGS TO SEE + DO: Sylvester Manor Educational Farm - farm stand + theatre + live music in summer months (4 miles), Shelter Island Historical Society (5 miles), Horton Point Lighthouse Nautical Museum (12 miles), The Hamptons (16 miles), Parrish Art Museum (18 miles), Long Island Aquarium (29 miles), Montauk Point Lighthouse Museum (37 miles) GET OUTSIDE: Lower Beach (1 mile), Upper Beach (3 miles), Coecles Harbor Marina & Boatyard (4 miles), Mashomack Preserve Entrance - walking trails (5 miles), 67 Steps Beach (8 miles), Sagg Main Beach - surfing, deep sea fishing, water sports (17 miles) WINE & DINE: Ram's Head Inn (0.9 miles), Marie Eiffel Market (5 miles), Vine Street Cafe (5 miles), Greenport Harbor Brewing Company (7 miles), Kontokosta Winery (8 miles), One Woman Winery Greenport (10 miles), The Old Field Vineyards (10 miles), Sparkling Pointe Vineyards & Winery (12 miles), Channing Daughters Winery (13 miles), Wölffer Estate Vineyard (14 miles) AIRPORTS: Long Island MacArthur Airport (58 miles), Laguardia Airport (101 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: There are a few steps required for entry, but there is a bedroom and bathroom with a zero-entrance shower on the main floor - NOTE: The outdoor pool is open seasonally from May-September and the kayaks are only available in the spring and summer months Licence number: 2023-V-0002

Sag Harbor Seclusion

Sag Harbor, NY, US
4 Bedrooms 8 Guests
Sep 16 - 29
$1,082 night

Sag Harbor Seclusion Stunning Contemporary Sag Harbor Estate, Minutes to Sag Harbor Village, Perfect for Families 4BR/3.5BA: private heated pool, outdoor shower, fire pit, work out equipment, work-from-home space, speakers, gas BBQ, ping-pong table Revel in luxury amenities, timeless Hampton style and tranquility this Summer at Sag Harbor Seclusion. This entertainers dream of a vacation home offers immaculate outdoor living and a coveted spot along the South Fork. Beautifully fused with classic architectural excellence and chic interior, this enchanting home aims to inspire. Whether youre planning a family gathering or a friend’s gathering, accommodations will exceed your expectations with four bedrooms and 3.5 bathrooms comfortably sleeping up to eight guests. Primely located in one of the most private areas along the South Fork, you are surrounded by Noyac Bay and across the street from Stock Farm preserve. Enjoy kayaking along Ganet Creek or basking in the sun with your favorite book on Foster Memorial beach. Showcased by cool interior tones, open living, sun-splashed spaces and beautiful hardwood flooring, prepare for both full scale entertainment and relaxation. Catch up on work in the dedicated work-from home space, or get your heart pumping in the work out area. Hire a private chef to prepare meals for the home from your designer kitchen boasting top of the line appliances, center island with breakfast bar top, and seamless access to the rear deck. Upstairs, relax into your luxe Primary suite featuring a comfy King bed and private balcony access. Enjoy a soothing bubble bath from your soaking tub in the Primary ensuite bath. Three remaining bedrooms plus two and a half baths complete this home. Outdoors, entertain family and friends from your private backyard oasis equipped with a gorgeous heated pool, ping-pong table, polished landscaping, ample seating and areas to truly relax. Never feel the need to leave this stunning estate as it checks off every box with gas BBQ, outdoor shower, outdoor dining area, and fire pit. Conveniently located along Sag Harbor, you are just minutes from the most beautiful beaches along the East coast plus a vibrant selection of local shopping and dining. Everlasting memories are yours to enjoy at Sag Harbor Seclusion. This property has a max occupancy of 8 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Walk-in Closet, Balcony/Deck Bedroom 2: One King Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet, Balcony/Deck Bedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Additional Sleeping Space: One Sleep Sofa, First Floor/Main Floor, Air Conditioning, Streaming TV, Private (Enclosed) Privacy Bathrooms Bathroom 1: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, 2nd Floor, Shower Bathroom 3: Full Bath, First Floor/Main Floor, Shower Bathroom 4: Half Bath, First Floor/Main Floor TVs Bedroom 1 Bedroom 3: Streaming Bedroom 4: Streaming Additional Sleeping Space: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Gas), Outdoor Shower (Hot + Cold Water), Tennis Court (Communal), Tennis Equipment (Rackets, Balls), Balcony, Beach Chairs (4 Chairs), Cooler, Fence Around The Yard, Beach Umbrella, Bicycle (2 Adult Bikes), Private Pool (Outdoor, Heated, Saltwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Ice Maker, Dishwasher, Microwave, Coffee (Nespresso, Other), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Bluetooth Speaker, Stereo), Gym/Fitness Room (Weight Training Equipment, Stretching / Yoga Mat), Ping Pong Table, Parking (3 Cars In Driveway), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Laptop-Friendly Workspace, Pots and Pans Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 2,700 Rental Registration: R-2025-0009 expires on 6/13/2027. Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: One dog of 20 lbs or less is permitted for an additional $350.00 per night. Dogs over 20 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $110.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: A refundable cash security deposit of $5,000 is required for this property. Information with respect to the payment and administration of the security deposit is governed by a separate Security Deposit Agreement between owner and guest, that shall be signed by both parties prior to check-in. This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Meadowood Manor | 6BR Outdoor Spaces

Sag Harbor, NY, US
6 Bedrooms 12 Guests
Sep 28 - Oct 1
$513 night

Welcome to Meadowood Manor, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Experience the best of the Hamptons in style at Meadowood Manor, a luxurious home located in the heart of Sag Harbor. Offering a selection of amenities including a salt water pool, outdoor shower, and a private full basketball/tennis court, guests can relax, unwind, and enjoy the great outdoors. Inside, the open floor concept with an expansive living space and fully-stocked kitchen is perfect for lounging, and 6 luxurious bedrooms provide an idyllic retreat for any group. Conveniently located near Sag Harbor Village and Bridgehampton, as well as a selection of fantastic beaches and restaurants, every amenity you need is at your fingertips for an unforgettable experience. Whether you’re seeking a summer or year-round retreat, Meadowood Manor is the perfect luxury rental property for you. To finalize your reservation, all guests must pass a mandatory third-party screening process. Pet Policy: Pets are allowed at this property for an additional $150 fee. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. Please note that bookings at this property are restricted to guests aged 30 and over. Parties are strictly prohibited, and any request to exceed the maximum occupancy will require owner approval. Please note the pool is serviced on Tuesdays during the open season, and both the pool and hot tub are closed during the winter months. Landscaping, seasonal pool maintenance, and pest control maintain periodic service schedules that may take place during your stay. The pool and hot tub are currently closed and will be guest-ready starting May 21, 2026. They are open seasonally and, weather permitting, may remain open through the end of September and potentially into mid-October. Our pool is cleaned and chemically balanced weekly. As an open-air pool, natural debris from wind and breeze are normal between service visits — a skimmer net is available for your convenience. Our team is always happy to assist if needed. If you want the pool heated during your stay, there is an additional $75/night fee. Note, utilities including pool heating are billed separately for all stays over 14 nights. The pool is open seasonally. The jacuzzi jets in the primary bathroom are not functional. Please note, a required propane fee of $75 per day applies to all stays. Parking Details: Cars can park in the driveway of the property and there is plenty of space for parking. The garage is not accessible. As a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of $1,000 as well as possible removal from the property. Security deposit Stays up to 13 nights: $2,500 credit hold Stays between 14 and 179 nights: $5,000 credit hold Stays of 180 nights or longer: Cash security deposit equal to one month’s rent

North Fork Chic

Peconic, NY, US
4 Bedrooms 8 Guests
Sep 20 - 23
$452 night

North Fork Chic Newly Renovated, Stylish Peconic Retreat with Private Pool, Lush Grounds, Perfect for Families. 4BR/2.5BA: Private heated pool, outdoor dining, gas BBQ, movie den, and chic interiors. Tucked away in the heart of the Long Island wine country, this newly renovated 1890s farmhouse is a picture-perfect escape for sophisticated travelers seeking serenity, style, and the timeless charm of the North Fork. Ideal for families and groups, the home offers the best of both worlds: a peaceful retreat enveloped by nature and easy access to beaches, acclaimed restaurants, and the areas thriving cultural scene. From the moment you arrive, youll feel the calm set insurrounded by lush greenery, expansive outdoor spaces, and modern, thoughtfully curated interiors that invite you to unwind, reconnect, and indulge in laid-back luxury. Step outside and discover your own private backyard oasis that feels more like a boutique resort than a vacation rental. The sprawling, sun-drenched yard is framed by mature landscaping, offering complete privacy and a beautiful natural backdrop for your stay. At the heart of the space is a fully fenced, heated pool; perfect for leisurely afternoon swims or energizing morning laps. Multiple lounge areas are scattered throughout, offering both sun-soaked and shaded spots to sip your morning coffee, read a book, or toast to the evening with a chilled glass of local chardonnay. A shaded outdoor dining area and a sleek gas grill ready for summer feasts and sunset dinners al fresco. Whether you’re dining poolside, enjoying cocktails under the stars, or lounging with loved ones, every moment here is designed to help you slow down and savor the good life. Ample on-site parking ensures ease for your entire group, whether you’re arriving solo or caravanning in with friends. Inside, the home blends timeless Hamptons charm with elevated modern touches. The spacious layout welcomes you with thoughtfully preserved historic details and comfort; brightened by natural light that pours through large windows and glass doors. The main level features multiple formal living spaces, including a sitting room perfect for relaxed conversation, and a cozy movie den with a plush sectional for late-night films or rainy-day lounging. The kitchen is a true highlight of the home, featuring top-of-the-line appliances, generous counter space, and all the culinary essentials needed to craft meals at home. Whether you’re preparing a casual brunch or a multi-course dinner, this kitchen is designed to inspire. The formal dining room comfortably seats eight and creates an inviting setting for celebratory meals and long conversations over wine. Thoughtfully equipped with high-speed WiFi, dedicated work-from-home nooks, central AC, and a washer/dryer, the home is as practical as it is stylish; ensuring you can settle in and feel right at home. When its time to unwind guests will find four beautifully appointed bedrooms upstairs, each designed with comfort in mind. The spacious primary suite offers a luxurious king bed and a spa-inspired ensuite bathroom with a walk-in shower; ideal for those who desire a bit of extra privacy. Three additional guest bedrooms provide flexible sleeping arrangements for the whole group. One features a king bed, another offers a queen, and the third is furnished with a bunk bed and an extra twin. These bedrooms share a bright hallway bathroom with a shower/tub combo, making mornings and evenings smooth and efficient for families or groups. A convenient powder room on the main level ensures comfort and accessibility throughout the day. Beyond the comfort of the home, guests are perfectly situated to enjoy the best of the North Fork. A short walk down scenic Peconic Lane brings you to a community park with tennis and pickleball courts, a playground, and open green space. Start your morning with a coffee and pastry from Panoramica, the neighborhood’s new hotspot, then browse the curated selection at Chronicle Wines; a standout local wine shop. Just down the road, the Greenport Brewery beer garden offers live music, local brews, and a laid-back space for families and friends to gather. For a change of pace, spend the afternoon at nearby Goldsmiths Inlet or Bailie Beach Park, where white sand and calm waters await. Or take a short drive to the charming villages of Greenport & Southold to explore art galleries, boutique shops, and local farm stands. More culinary delights are just minutes away, from fresh oysters at Little Creek to wood-fired pizza at 1943 Pizza Bar, and fine dining at North Fork Table & Inn. Wine lovers will appreciate proximity to some of the regions most renowned vineyards and tasting rooms, including Pindar, Lenz, and Bedell Cellars. Whether youre biking through vineyard trails, exploring the local farmers markets, or enjoying a quiet beach day, this home offers a central location for soaking in the areas natural beauty and relaxed elegance. With its effortless indoor-outdoor flow, stylish interiors, and unbeatable location, this chic Peconic retreat is an invitation to experience the North Fork at its finest. Whether you’re here for a long summer holiday or a weekend getaway, every detail is curated for comfort, connection, and unforgettable memories. This property has a max occupancy of 8 Bedrooms Bedroom 1 - Primary: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2 - Guest: One Queen Bed, 2nd Floor, Air Conditioning Bedroom 3 - Guest: One King Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 4 - Bunk Bed: One Bunk Bed, One Twin Single Bed, 2nd Floor, Air Conditioning, Standard Closet Bathrooms Powder Room: Half Bath, First Floor/Main Floor Bathroom 1 - Primary ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 2 - 2nd Floor Hall: Full Bath, 2nd Floor, Shower/Tub Combo TVs Bedroom 1 - Primary: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Fence Around The Pool, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Lounge Chairs, Private Pool (Heated, Outdoor, Saltwater) Amenities Bed Linens, Air Conditioning (Central Air), Dryer, Internet (Wifi), Washer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Television (Den), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Ice Maker, Laptop-Friendly Workspace, Essentials, Hair Dryer, Heating, Toaster, Blender, Pack 'n Play/Travel Crib, Fire Extinguisher Location Nearby Beaches: Horton Lane Beach Nearby Grocery Stores: Southold IGA Wayside Market Nearby Restaurants and Bars: Bedell Cellars Pindar Vineyards Duck Walk Vineyards North Fork Table & Inn La Cascada Greenport Brewery Other Location Information: Founders Landing Park Horton Point Lighthouse Nautical Museum Other FAQ’s Pool Fenced In: Yes Suitability: Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $125.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Coves Bay Beauty

Sag Harbor, NY, US
5 Bedrooms 10 Guests
Oct 26 - Nov 2
$641 night

Coves Bay Beauty Modern Coastal Farmhouse style home with a private pool, open-floor plan, grand back deck, located a quick walk/bike to beaches & town 5BR/4BA - Gallery hallway, chef's kitchen, ample parking, entertainer's patio, Cozy Earth linens, beach cruisers, and more! Perched near Sag Harbor Cove lies this charming, modern coastal farmhouse-style home with a private pool, open-floor plan, and beautiful backyard. Upon entering the home, you will immediately be struck by the bright and airy atmosphere illuminated with natural light. There are two living rooms one with double height ceilings neighboring a dining table comfortably set for ten. Novice and well-seasoned chefs are welcome to cook in the gourmet kitchen that comes with an oversized island, stainless steel appliances, and ample counter space for meal prep or laying out hors doeuvres. During the day, curl up with your favorite book and relax on any one of the loungers adjacent to the glistening pool. Head to one of the nearby beaches a 10 minute walk to Foster Memorial Town Beach and 5 minute drive to Havens Beach you have nothing but wonderful options. As the sun begins to set, hop on a provided beach cruiser and venture into downtown Sag Harbor for sight-seeing, shopping, and renowned local restaurants. Retire to one of the spacious bedrooms for a peaceful nights sleep, or stargaze with a nightcap from the upstairs deck. For unparalleled sleep and leisure, each bed in this property is made with temperature-regulating and luxuriously soft bamboo viscose linens by Cozy Earth. Rest assured, there is plenty of drawer and closet space to completely unpack and settle in. With new coastal furnishings, pool, and wonderful amenities, this Coves Bay Beauty has all the makings for a memorable stay! This property has a max occupancy of 10 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 3: Two Double/Full Beds, 2nd Floor, Air Conditioning, Streaming TV, Walk-in Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Walk-in Closet Bedroom 5: One Queen Bed, First Floor/Main Floor, Air Conditioning, Walk-in Closet Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower Master Bath: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 4: Full Bath, 2nd Floor, Shower, Tub TVs Bedroom 1: Streaming Bedroom 2: Streaming Bedroom 3: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Outdoor Shower, Balcony, Bicycle (4 Adult Bikes), Fence Around The Yard, Beach Chairs (4 Chairs), Cooler, Grill (Gas), Beach Umbrella, Beach Toys, Private Pool (Outdoor, Heated, Saltwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Dishwasher, Microwave, Coffee (Pot, Keurig, Other), Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Main Living Room), Smart TV, Parking (4 Cars In Driveway), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Toaster, Blender, Iron/Ironing Board, Laptop-Friendly Workspace, Pots and Pans, Essentials, Ice Maker, Pack 'n Play/Travel Crib Location Nearby Beaches: Foster Memorial Beach Havens Beach Nearby Grocery Stores: Schiavoni’s Market Cavaniola’s Gourmet Kitchen Provisions Cromer’s Market Nearby Restaurants and Bars: Tutto il Giorno The American Hotel Page at 63 Main Lulu Kitchen & Bar Baron’s Cove Dockside Bar & Grill Grindstone Coffee and Donuts Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 3,250 The gas fireplace is unavailable for use until further notice. Rental Registration: 12 expires on 3/19/2027. Suitability: Not handicap accessible. Not suitable for unrelated guests. Primary renter must be at least 30 years old. Pet Policy: One dog of 25 lbs or less is permitted for an additional $500.00 per booking. Dogs over 25 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $110.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. An additional guests fee of $150.00 per person per night may be required. Events Policy: Events are prohibited unless express approval is provided. An event fee of $2,000.00 may be required. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Sag Harbor Estate

Sag Harbor, NY, US
5 Bedrooms 10 Guests
Sep 16 - 18
$3,020 night

Please note that a reservation for this property needs to be approved before it is confirmed. Sag Harbor Estate Stunning Sag Harbor Estate on Over 3 Acres, Pool, Tennis, Perfect for Families 5BR/6BA: private heated pool, hot tub, tennis court, pool table, gym, sundeck, pool house, gas BBQ, outdoor dining, sonos speakers Situated on over three pristine acres in Sag Harbor, this expansive estate offers the ultimate combination of luxury and tranquility. Boasting five bedrooms and six bathrooms, the homes open floorplan is bathed in natural light and designed to inspire relaxation and connection. With a maximum occupancy of 10, this sophisticated retreat is perfect for families or groups seeking an unforgettable escape from the bustle of daily life. Set on a private and picturesque block, the estate offers seamless indoor and outdoor living, inviting you to soak in the beauty of the surrounding landscape. Step into a world of serenity and sophistication as you explore the estates exceptional outdoor amenities. The private heated pool beckons for leisurely swims, while the adjacent hot tub offers a soothing retreat under the stars. Sports enthusiasts will delight in the private tennis court, perfect for a morning match. Expansive decks and a spacious patio provide endless options for al fresco dining and lounging, with a large outdoor dining table, a gas BBQ for grilling, and multiple sitting areas ideal for cocktails and conversation. The lush, manicured yard offers ample space for children to play or for quiet moments of reflection. A well-appointed pool house adds a touch of convenience and luxury, while a sundeck offers the perfect spot to bask in the Hamptons sunshine. With plenty of free parking, this estate ensures that every guest experiences effortless comfort. As you enter the home, you are greeted by a grand, double-height living room, where expansive windows invite natural light to flood the space. The open layout flows effortlessly, connecting the living room, dining room, and gourmet island kitchen. Gather by the inviting fireplaces in the living room, or linger in the state-of-the-art kitchen, equipped with top-of-the-line appliances and a coffee maker for your morning indulgence. Modern conveniences abound, with high-speed WiFi, central air conditioning, and a washer and dryer to meet all your needs. For those working remotely, a dedicated work-from-home space provides the ideal balance of productivity and relaxation. The finished lower level is a hub of entertainment, featuring a full gym, a billiards table, and an additional media area, ensuring that every moment indoors is as engaging as it is comfortable. Each of the five bedrooms offers a serene and private haven, complete with fresh, high-quality linens and plush furnishings. Designed with relaxation in mind, these spacious retreats ensure every guest feels at home. The en-suite bathrooms feature all the essentials for a spa-like experience, providing the perfect place to unwind and refresh after a day of exploring Sag Harbor. This remarkable estate is ideally situated just minutes from the charming village of Sag Harbor. Indulge in the towns vibrant culinary scene, browse its boutique shops and art galleries, or pick up fresh produce from local farm stands. Short Beach, a local favorite, is a stones throw away, offering sun-soaked days and picturesque sunsets. Whether youre seeking a serene escape, a place to connect with loved ones, or a base for exploring the Hamptons, this Sag Harbor estate is a destination in itself. From its elegant interiors to its expansive outdoor amenities, every detail is designed to create a memorable and luxurious experience. This property has a max occupancy of 10 Bedrooms Bedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom Primary Bedroom 2: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 4: One King Bed, 2nd Floor, Air Conditioning Bedroom 5: One King Bed, 2nd Floor, Air Conditioning, Streaming TV, Walk-in Closet, Balcony/Deck Bathrooms Bathroom 1: Half Bath, First Floor/Main Floor Bathroom 2: Half Bath, First Floor/Main Floor Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Tub Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 6: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 7: Full Bath, Lower Level, Shower TVs Primary Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 5: Streaming Outdoors & Pool/Spas Balcony, Bicycle, Deck/Patio (Covered), Grill (Gas), Tennis Court (Private), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Tennis Equipment (Rackets, Balls), Fence Around The Pool, Fence Around The Yard, Hot Tub (Hot Tub Attached to Pool), Private Pool (Heated, Outdoor, Freshwater) Amenities Bed Linens, Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Gym/Fitness Room (Stationary Bike), Garage, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Pool Table, Speaker System (Sonos), Television (Main Living Room), Private Entrance, Steam Room, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Wine Fridge, Ice Maker, Laptop-Friendly Workspace, Fire Extinguisher, Essentials Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Suitability: Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: A refundable cash security deposit of $5,000 is required for this property. Information with respect to the payment and administration of the security deposit is governed by a separate Security Deposit Agreement between owner and guest, that shall be signed by both parties prior to check-in. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Stunning Contemporary Compound in Sag Harbor with Private Pool and Tennis Court

Sag Harbor, NY, US
5 Bedrooms 12 Guests
Dec 27 - 29
$1,032 night

Merchant Estate Live the good life and escape out east to Sag Harbor/Wainscott! 5BR/ 6.5 BA w/ Tennis on 5 + acres with Pool, Hot Tub & Sauna, open plan living / dining room / Kitchen and so much more! Escape Out East to Sag Harbor! Live the good life on this remarkable, 5.4 acre gated compound. There’s no doubt you’ll fall in love with the Hamptons, as you enjoy a peaceful stay at this private retreat! This stunning contemporary home sleeps 12, with five en-suite bedrooms, including three master suites, one on the first level with a sauna and a private deck. The sun-filled open concept living room features a cathedral ceiling, skylights, a gas-burning fireplace, and an open dining room with French doors leading to a covered porch. The spectacular state of the art kitchen features Subzero and Wolf appliances as well as a miele and nespresso machines. Additional highlights include a fully finished lower level with ping pong and pool tables, office set up and an additional queen pull out bed. You and your guests will love the convenience of the 7 smart TVs, 5 separate Sonos zones inside and a 6th outside, the Mesh wifi system (gigabyte internet) by Optimum, and the Samsung dryer and washer. In the sun-filled study guests will find a fully functioning office setup complete with a laser printer and IMAC computer. Additional features include top of the line mattresses on each of the beds, a peloton bike and brand new furniture throughout. The north wing master suite features a wood burning fireplace, a private study, a jacuzzi tub and a double shower. In the south wing master suite, you will find 20 foot ceilings, a surround sound system, an additional gas burning fireplace, soaking tub and a double rain head shower. Step outside for some fresh air and enjoy beautiful views of the large grounds featuring a heated gunite pool plus a 10 seat hot tub, a secluded and lighted tennis court, with separate covered entertaining space as well as a fire pit area. Guests can enjoy the use of adult and childrens bicycles, beach chairs, a paddleboard and even a kayak. The home is surrounded by miles of nature preserve trail systems and private ponds to discover. Prepare to fall in love with the Hamptons lifestyle, as you experience it at its very best! This property is a 5 minute drive to Sag Harbors Main Street and 7 minutes to East Hampton. This property has a max occupancy of 12 and can accommodate bunk beds for an additional cost. This property has a max occupancy of 12 Bedrooms Bedroom 1 - Master Suite: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 4 - Second Master Suite: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 5: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom Additional sleeping space: One Sleep Sofa, Lower Level, Air Conditioning Bathrooms Bathroom 1 - Master Suite: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 4 - Second Master Suite: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5: Full Bath, 2nd Floor, Ensuite, Jack & Jill, Shower Bathroom 6: Full Bath, Lower Level, Shower Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Tennis Court (Private), Fence Around The Yard, Fence Around The Pool, Fire Pit (Wood-Burning), Bicycle (3 Adult Bikes), Beach Chairs (6 Chairs), Beach Umbrella, Kayak/Canoe, Paddle Board, Private Pool (Outdoor, Heated), Hot Tub (Hot Tub Attached to Pool) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee, Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Sonos), Ping Pong Table, Private Entrance, Parking, Garage (2 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Laptop-Friendly Workspace, Pots and Pans, Sauna Special Features A temporary pool fence is available for use upon request. Other FAQ’s Backyard Fenced In: Yes This property requires a Refundable Deposit of 20% of the Total Rate which will cover Security Deposit and Utilities. Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. When the pool is open, a temporary pool fence is available for use upon request. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: A refundable cash security deposit of $7,500 is required for this property. Information with respect to the payment and administration of the security deposit is governed by a separate Security Deposit Agreement between owner and guest, that shall be signed by both parties prior to check-in. This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Northwest Harbor Contemporary

East Hampton, NY, US
4 Bedrooms 8 Guests
Sep 28 - 30
$824 night

Northwest Harbor Contemporary Classic East Hampton Home Perfect for Families Close to Town and Beaches 4BR/3BA: private salt water pool, hot tub, island kitchen, fireplace, marble countertops, multiple sitting areas, office, pool table Welcome to Northwest Harbor Contemporary in East Hampton! This stunning 4 bedroom, 3 bathroom home is the perfect destination for families and friends looking to escape to the Hamptons. As you enter the home, you will be greeted with an open layout, plenty of natural light, and open living spaces. The island kitchen is perfect for preparing meals and entertaining guests, and the dining room table seats 8 people comfortably. The living room features a big screen TV and access to the deck, making it the perfect spot for movie nights or enjoying a glass of wine in the evenings. The double height living room is the perfect spot for lounging with friends and family, and the fireplace adds to the cozy and welcoming atmosphere. The basement even comes equipped with a Peloton, for those who want to stay active during their vacation. Step outside and you will find an array of amenities to enjoy during your stay. Take a dip in the pool, hot tub, or lounge on the chairs while soaking up the sun. The outdoor dining table is perfect for al fresco meals, and the surrounding lush greenery provides a serene and peaceful backdrop. The bedrooms and bathrooms in this home are just as impressive as the rest of the property. The ensuite primary bathroom is beautifully designed and has all the essentials you will need during your stay. The other bathrooms are also well-appointed, ensuring that everyone has a comfortable and relaxing experience. Northwest Harbor Contemporary is located close to art galleries, restaurants, the town center, and the beach, making it the perfect base for exploring all that the Hamptons has to offer. Whether you are looking to relax and unwind or explore and adventure, this property is sure to exceed your expectations. Please note - hot tub is available year-round. No Smoking Policy For the comfort and safety of all guests, smoking is strictly prohibited anywhere on the property, including both indoor and outdoor spaces. Doing such may incur a penalty fee. This property has a max occupancy of 8 Bedrooms Primary Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Guest Bedroom 2: One Double/Full Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Guest Bedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet Guest Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet Additional Sleeping Space: One Sleep Sofa, First Floor/Main Floor, Air Conditioning, Streaming TV Bathrooms Primary Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Guest Bathroom 2: Full Bath, First Floor/Main Floor, Shower Guest bathroom 3: Full Bath, 2nd Floor, Shower, Tub TVs Primary Bedroom 1: Streaming Guest Bedroom 2: Streaming Guest Bedroom 3: Streaming Guest Bedroom 4: Streaming Additional Sleeping Space: Streaming Outdoors & Pool/Spas Deck/Patio, Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Beach Chairs, Cooler, Fire Pit (Wood-Burning), Fence Around The Pool, Private Pool (Outdoor, Heated, Saltwater), Hot Tub (Freestanding Hot Tub) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Private Entrance, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Laptop-Friendly Workspace, Television (Main Living Room, Kitchen, Den, Office), Hair Dryer, Parking, Coffee (Pot, Other), Toaster, Blender, Smart TV, Ice Maker, Wine Fridge, Speaker System, Usable Fireplace (Gas-Burning), Pool Table, Privacy (Completely Private) Other FAQ’s Pool Fenced In: Yes Estimated Square Footage: 2,700 Suitability: Not handicap accessible. Primary renter must be at least 25 years old. Pet Policy: One dog of 50 lbs or less is permitted for an additional $250.00 per booking. Dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $135.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: April to mid October Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Bayside Serene

Sag Harbor, NY, US
3 Bedrooms 6 Guests
Sep 20 - 23
$549 night

Bayside Serene Modern Sag Harbor Escape, Moments from the Water and Long Beach to View Amazing Sunsets, Perfect For Families 3BR/2.5BA: Brand new heated pool, outdoor dining, private yard, chic interiors, close to town and beaches Nestled in the heart of Sag Harbor, this modern and chic home offers the perfect blend of contemporary comfort and coastal charm. Ideally located just steps from the water and a short distance to Sag Harbor’s charming village center, guests will find themselves within easy reach of pristine beaches including Long Beach, renowned restaurants, and boutique shopping. The homes sleek, open floor plan is designed for effortless living, with an abundance of natural light streaming through sliding glass doors that lead directly to the private backyard. Guests will enjoy the luxury of a brand new private pool, promising a serene and exclusive holiday experience. Boasting three well-appointed bedrooms and two and a half baths, this property comfortably accommodates up to six guests, making it the ideal retreat for families or a small group of friends seeking a stylish escape from daily life. Step outside to discover the homes beautifully designed outdoor spaces. The private, tree-lined yard offers a peaceful oasis where guests can relax and unwind. The outdoor deck is the perfect place for enjoying morning coffee or evening cocktails. A covered patio with a dining table invites alfresco dining, whether it’s a casual lunch or a sunset dinner under the stars. The private heated pool is the centerpiece of the expansive yard, where guests can relax or play in seclusion. Thoughtfully landscaped for privacy and tranquility, the yard provides the perfect setting for sunbathing, socializing, or simply soaking in the quiet surroundings. With plenty of free parking available, coming and going is effortlessthough you may find yourself wanting to stay put and savor the laid-back Sag Harbor lifestyle. Inside, the homes modern architecture and chic furnishings create a stylish yet inviting atmosphere. The open-concept living spaces are anchored by a spacious living room with plush seating and large windows that bathe the room in natural light. Sliding glass doors seamlessly connect the living and dining areas to the backyard, creating a smooth indoor-outdoor flow that enhances the sense of space and relaxation. The sleek, fully equipped kitchen serves as the heart of the home, outfitted with state-of-the-art appliances, a coffee maker, and all the cooking essentials needed to prepare meals with ease. A large island provides extra prep space and serves as a natural gathering spot for morning coffee or evening cocktails. High-speed WiFi, central AC, and a washer and dryer ensure every modern convenience is at your fingertips. Upstairs, the three well-appointed bedrooms provide a peaceful and restful retreat. The primary suite features a spacious and bright sitting area with a couch and chairs, and an ensuite bathroom with a modern vanity and walk-in shower. Up the private staircase you’ll find the lofted sleeping area, complete with a king-size bed and large windows. The two additional bedrooms, each designed to comfortably accommodate two adults, share a stylish hall bath with contemporary fixtures and a combination tub and shower. All bedrooms are dressed in crisp, fresh linens and outfitted with thoughtful touches to enhance your stay. A convenient powder room with a washer and dryer is located on the main floor, adding to the homes ease and functionality. This home places you within easy reach of Sag Harbors best attractions. Start your morning with a leisurely stroll to the nearby waters edge, or take a short drive to one of the areas renowned beaches. The vibrant village center is just minutes away, where youll find charming cafes, upscale boutiques, and art galleries showcasing work from local and international artists. Food lovers will appreciate Sag Harbors diverse dining scene, from fresh seafood at The American Hotel to farm-to-table cuisine at Lulu Kitchen & Bar. Golf enthusiasts can enjoy a round at the nearby Noyac Golf Club, while wine lovers will appreciate tastings at Wlffer Estate Vineyard, just a short drive away. Seasonal farm stands offer fresh produce and local specialties, perfect for stocking the kitchen or creating a picnic for a beach day. Many of these attractions are easily accessible by bike or a short walk, allowing you to fully immerse yourself in the laid-back yet refined Sag Harbor lifestyle. This modern Sag Harbor retreat offers the perfect combination of style, comfort, and convenience. Whether youre spending your days lounging by the water, exploring the vibrant local scene, or simply relaxing at home, this chic and thoughtfully designed property provides the ideal backdrop for an unforgettable getaway. This property has a max occupancy of 6 Bedrooms Bedroom 1 - Primary (Loft): One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2 - Guest: One King Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3 - Guest: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bathrooms Bathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2 - Upstairs Guest: Full Bath, 2nd Floor, Shower/Tub Combo First Floor Powder: Half Bath, First Floor/Main Floor, Handicap Accessible TVs Bedroom 1 - Primary (Loft): Streaming Outdoors & Pool/Spas Deck/Patio (Covered), Patio Furniture (Table, Chairs), Grill (Gas), Lounge Chairs (2 Chairs), Fence Around The Yard, Private Pool (Outdoor, Heated) Amenities Bed Linens, Air Conditioning, Dryer, Heating, Washer, Hair Dryer, Microwave, Kitchen, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Internet (Wifi), Living Room, Parking, Bath Towels, Dishes and Silverware, Pots and Pans, Television (Main Living Room), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Smart TV, Laptop-Friendly Workspace, Speaker System, Private Entrance, Essentials, Coffee Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Long Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Sag Habor State Golf Course Elizabeth A Morton National Wildlife Refuge Suitability: Primary renter must be at least 30 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $100.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Noyack Cottage

Sag Harbor, NY, US
2 Bedrooms 6 Guests
Sep 16 - Oct 14
$318 night

Please note that a reservation for this property needs to be approved before it is confirmed. Noyack Cottage Cozy Sag Harbor Home Minutes from the Beach, Restaurants, Town Shopping 2BR/2BA: with two additional sleeping spaces, fire pit, outdoor shower, expansive yard, Bluetooth speaker system Welcome to your tranquil getaway in Sag Harbor. This enchanting 2-bedroom, 2-bathroom vacation rental provides an additional two sleeping spaces, making it a perfect retreat for small families or couples seeking solace from the hustle of everyday life. Nestled on a beautiful, private block, this lovely cottage invites you to unwind and experience the charm and serenity of the Hamptons. Enter into a bright, spacious living area bathed in natural light, where comfort meets elegance. The open floor plan seamlessly connects the living room, dining area, and kitchen, encouraging laughter and conversation to flow as freely as the interior space. Each corner of the home speaks of attention to detail, inviting you to make yourself at home. The airy living room, adorned with plush, comfortable seating, creates an ideal setting for relaxing moments or lively get-togethers. The dining room beckons for memorable meals and the kitchen, equipped with top-of-the-line appliances, ensures your culinary escapades are as enjoyable as they are tasty. Venture downstairs to the finished lower level, where you’ll discover a cozy sitting area for quiet conversations or engrossing reads. A luminous sunroom, complete with a dining table, offers a panoramic view of natures artwork, ushering in the calm of the outdoors. Step outside to an expansive patio, where the Sag Harbor landscape unfurls before you. Revel in the luxury of total privacy and take advantage of the plentiful outdoor amenities. The patio hosts a large dining table, perfect for alfresco meals and evening soirees under the starry Hamptons sky. A gas BBQ waits for the grill master, and multiple seating areas invite quiet contemplation or lively discussions. Refresh under the outdoor shower after a day at the beach, or gather around the fire pit, where stories ignite as easily as the warm flames. For the active guest, communal tennis courts are but a stone’s throw away, ready to serve up friendly competition. Inside, retire to the tranquil bedrooms, where fresh linens and soft pillows promise restful slumbers. Each bathroom, well-appointed and sparkling clean, comes stocked with all the essentials you need to feel refreshed and revitalized each morning. The comfort and convenience extend beyond the main rooms, creating a home away from home for our guests. The prime location places you close to the best Sag Harbor offers. A brief stroll takes you to breathtaking beaches, where sun, surf, and sand unite to form the perfect coastal getaway. Indulge in the local cuisine at nearby restaurants, shop at unique boutiques, or peruse the varied art galleries lining our streets. Golf enthusiasts can tee off at well-maintained golf courses in the vicinity. Everything you need for an unforgettable stay is within your grasp. This property has a max occupancy of 6 Bedrooms Bedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 2: One Double/Full Bed, 2nd Floor, Air Conditioning Sunroom Sleeping Area: One Sleep Sofa, First Floor/Main Floor, Air Conditioning, Open Area Privacy Lower Level Common Area: Two Sleep Sofas, Two Twin Single Beds, Lower Level, Air Conditioning, Privacy Bathrooms Bathroom 1: Full Bath, 2nd Floor, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower/Tub Combo Outdoors Deck/Patio (Uncovered), Grill (Gas, Charcoal), Tennis Court (Communal), Beach Chairs, Outdoor Shower (Hot + Cold Water), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Tennis Equipment (Rackets, Balls), Fire Pit (Wood-Burning), Cooler Amenities Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Speaker System (Bluetooth Speaker), Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Cable TV, Smart TV, Laptop-Friendly Workspace Special Features Noyack Old School House (right next to the property) Elizabeth Morton National Park Short drive to Ferry to Shelter Island Location Nearby Beaches: Clam Island Park Beach 7mins walking distance 5mins drive to the long beach Nearby Grocery Stores: 2mins driving Kromer Market Nearby Restaurants and Bars: 5mins drive to Sag Harbor town restaurants Other Location Information: 5mins drive to museums in Sag Harbor Suitability: Not handicap accessible. Primary renter must be at least 21 years old. Pet Policy: One dog of 25 lbs or less is permitted for an additional $250.00 per booking. Dogs over 25 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $50.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Sag Harbor Grand

Sag Harbor, NY, US
7 Bedrooms 16 Guests
Sep 16 - Oct 14
$6,361 night

Sag Harbor Grand Expansive Sag Harbor Estate, Private Grounds with Stunning Pool & Hot Tub, Perfect for Group Gatherings 7BR/8.5BA: Heated Pool, Hot Tub, Communal Tennis Courts, Ping Pong Table, Pool Table, Gas Gril, Wood Burning Fireplace, and Gym Set on beautifully landscaped private grounds, this expansive Sag Harbor estate offers an exceptional setting for group gatherings, family celebrations, and relaxed coastal living. Thoughtfully designed to balance elegance with comfort, the seven-bedroom, eight-and-a-half-bath residence provides generous space to come together while still offering quiet moments of retreat. Tucked away on a peaceful private block, the home feels like a true escapewhere days unfold slowly, laughter carries easily from room to room, and every detail supports effortless time spent with those who matter most. The outdoor experience is nothing short of spectacular. Surrounded by lush greenery, the private grounds create a serene oasis designed for both relaxation and entertaining. A stunning heated pool serves as the centerpiece of the backyard, inviting guests to swim, lounge, and soak in the sunshine throughout the day. Nearby, a hot tub offers the perfect place to unwind in the evenings, whether after a day at the beach or a friendly tennis match at the communal courts. Multiple outdoor seating areas encourage conversation and connection, while the gas grill makes alfresco dining easy and enjoyable. The propertys sense of privacy allows guests to fully relax, creating a resort-like atmosphere where time seems to slow down. Inside, the home welcomes guests with light-filled interiors and an open, flowing floorplan that immediately feels both grand and inviting. Expansive windows flood the living spaces with natural light, highlighting the homes refined finishes and thoughtful design. The main living areas are perfectly suited for group gatherings, offering comfortable seating, a warm wood-burning fireplace, and an easy transition from living room to dining room and kitchen. Whether hosting a celebratory dinner or enjoying a quiet evening indoors, the spaces feel effortlessly connected and welcoming. The gourmet kitchen is a dream for both casual cooks and experienced hosts. Outfitted with top-of-the-line appliances, generous counter space, and a well-appointed coffee station, it supports everything from leisurely breakfasts to elegant dinners. The kitchen flows seamlessly into the dining area, allowing guests to stay connected while meals are prepared and shared. High-speed WiFi, central air conditioning, and a washer and dryer add everyday convenience, ensuring a comfortable stay no matter the season or length of visit. Entertainment options abound throughout the home. A dedicated game area with a pool table and ping pong table invites friendly competition, while a private gym offers space to maintain fitness routines even while away. These thoughtful amenities ensure there is something for everyone, whether guests are seeking activity or relaxation. The bedrooms are designed as peaceful sanctuaries, offering comfort, privacy, and a sense of retreat. With seven spacious bedrooms spread throughout the home, guests can enjoy restful nights wrapped in fresh, high-quality linens. Each bedroom is paired with a beautifully appointed bathroom, providing spa-like comfort and all the essentials needed for a seamless stay. The abundance of bathrooms ensures ease and convenience for large groups, making mornings and evenings feel unhurried and relaxed. Ideally located in Sag Harbor, this estate places guests within easy reach of the very best the Hamptons have to offer. Renowned restaurants, charming boutiques, art galleries, and cultural attractions are just a short drive away, as are world-class golf courses and the beautiful beaches of Southampton. Whether exploring the village, enjoying waterfront dining, or spending the day by the ocean, guests will find endless opportunities nearbywhile always returning to the tranquility of their private retreat. With its expansive layout, resort-style amenities, and prime Sag Harbor location, this exceptional estate offers an unforgettable setting for gatherings large and small. Designed to inspire connection, comfort, and lasting memories, it is a place where guests can truly settle in, unwind, and experience the Hamptons at its most inviting. This property has a max occupancy of 16 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 2 - Primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet, Balcony/Deck Bedroom 5: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 6: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 7 - Basement: Two Double/Full Beds, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Standard Closet Bathrooms Bathroom 1 - BA 1 Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower Bathroom 3 - Primary BR Ensuite: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 4 - BR 3 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 5 - BR 4 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 6 - BR 5 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 7 - BR 6 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 8 - Basement Half Bath: Half Bath, Lower Level Bathroom 9 - Basement Jack and Jill: Full Bath, Lower Level, Ensuite, Shower TVs Bedroom 1: Streaming Bedroom 2 - Primary: Streaming Bedroom 6: Streaming Outdoors & Pool/Spas Balcony, Deck/Patio (Uncovered), Grill (Gas), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard, Fire Pit (Wood-Burning), Tennis Court (Communal), Private Pool (Heated, Outdoor, Freshwater), Hot Tub (Hot Tub Attached to Pool) Amenities Bed Linens, Usable Fireplace (Gas-Burning), Air Conditioning (Central Air), Dryer, Internet (Wifi), Washer, Gym/Fitness Room (Elliptical, Stationary Bike, Weight Training Equipment, Stretching / Yoga Mat), Game Room, Garage (Attached, Available for renter cars), Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Ping Pong Table, Pool Table, Speaker System (Bluetooth Speaker), Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Smart TV, Wine Fridge, Ice Maker, Laptop-Friendly Workspace, Privacy (Completely Private), Heating, Hot Water, Essentials Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Suitability: Not handicap accessible. Primary renter must be at least 35 years old. Pet Policy: One dog of 20 lbs or less is permitted. Dogs over 20 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Cutchogue Villa

Cutchogue, NY, US
4 Bedrooms 11 Guests
Sep 20 - 23
$610 night

Please note that a reservation for this property needs to be approved before it is confirmed. Cutchogue Villa Elevated North Fork Escape with Chic Interiors and Private Poolside Oasis - Perfect for Families 4BR/3BA: office, private heated pool, fenced in yard, outdoor dining, gas BBQ, cozy fireplace, modern kitchen Tucked away on a private, picturesque lot in the heart of Cutchogue, this chic modern retreat offers the perfect North Fork escape. Thoughtfully designed with a blend of contemporary sophistication and earthy coastal charm, this luxurious 4-bedroom, 3-bathroom home delivers a true indoor-outdoor living experience ideal for families, couples, or friends looking to relax and reconnect. With sun-filled spaces, beautifully curated interiors, and resort-style amenities, every detail has been considered to create a peaceful and elevated getaway. Located just minutes from Cutchogues charming town center, beaches, acclaimed restaurants, and renowned wineries, this home offers the perfect balance of privacy, comfort, and convenience. Step outside into your own private oasis. The expansive, fully fenced backyard is designed for effortless summer living, featuring a stunning heated pool surrounded by a brand-new bluestone patio that creates an elegant space for lounging, entertaining, and enjoying long afternoons in the sun. Relax on comfortable chaise loungers, gather for dinner on the outdoor dining deck, fire up the gas grill for a backyard barbecue, or rinse off after a swim in the convenient outdoor shower. Surrounded by lush landscaping and mature greenery, the grounds feel both private and invitinga rare combination that makes every moment outdoors feel like a true retreat. Inside, the home showcases a modern coastal aesthetic with warm, natural finishes and an abundance of natural light. Vaulted ceilings, skylights, and oversized windows create an airy, open atmosphere throughout the main living spaces. The living room serves as the heart of the home, featuring comfortable seating, a sleek gas fireplace, and direct views of the pool through expansive sliding glass doors. The adjoining dining area and state-of-the-art kitchen make entertaining effortless, with high-end appliances, a spacious island, and everything needed for preparing memorable meals with family and friends. A separate media room offers a cozy setting for movie nights, while the finished lower level provides additional living space with a lounge area, queen sleeper sofa, and private officeperfect for guests blending work and leisure. With high-speed WiFi, central AC, a washer and dryer, and a full suite of modern amenities, the home is equally suited for a relaxing weekend escape or an extended stay. The four thoughtfully appointed bedrooms provide comfortable retreats for every guest. The main-level primary suite features a king-sized bed, spa-inspired ensuite bathroom with double vanities, and a luxurious walk-in rain shower. A second guest bedroom offers a queen bed, while a third bedroom includes a queen bed and full-sized crib, ideal for families traveling with young children. These rooms share a spacious hall bathroom with a shower/tub combination. The lower level features a fourth bedroom with bunk beds and access to a Jack-and-Jill-style bathroom, along with additional sleeping space in the lounge area. Beyond the property, guests can experience everything the North Fork has to offer. Nearby beaches such as New Suffolk Beach and Nassau Point provide the perfect setting for swimming, relaxing, and sunset strolls. Cutchogues charming local shops, farm stands, restaurants, and wineries are just minutes away, offering endless opportunities to explore the regions food, wine, and natural beauty. Spend the day wine tasting, biking scenic country roads, enjoying fresh seafood, or simply taking in the slower pace of North Fork living. More than just a vacation rental, this home is a destination in itselfan elevated yet welcoming retreat where modern luxury, natural beauty, and effortless relaxation come together. This property has a max occupancy of 11 Bedrooms Bedroom 1 - Primary: One King Bed, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, TV, Closet Bedroom 2 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Closet Bedroom 3 - Kids Bedroom: One Crib Bed, One Queen Bed, First Floor/Main Floor, Air Conditioning, Closet Bedroom 4 - Bunk Beds: Two Bunk Beds, Lower Level, Air Conditioning, Jack & Jill Ensuite Bathroom, Closet Office: One Sleep Sofa, Lower Level, Air Conditioning, Jack & Jill Ensuite Bathroom, Privacy Bathrooms Bathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2 - Guest: Full Bath, First Floor/Main Floor, Shower/Tub Combo Bathroom 3 - Lower Level: Full Bath, Lower Level, Ensuite, Shower TVs Bedroom 1 - Primary Outdoors & Pool/Spas Deck/Patio, Lounge Chairs, Patio Furniture (Table, Chairs), Grill (Gas), Beach Chairs, Cooler, Fence Around The Yard, Fence Around The Pool, Private Pool (Outdoor, Heated, Saltwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Gas-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot, Keurig), Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Main Living Room, Den), Smart TV, Speaker System (Bluetooth Speaker), Pack 'n Play/Travel Crib, Parking, Carbon Monoxide Detector, Smoke Detector, Essentials, Private Entrance Location Nearby Beaches: New Suffolk Beach Nassau Point Beach Peconic Bay Beach Southold Town Beach Cedar Beach (Southold) Nearby Grocery Stores: King Kullen Supermarket Wickham’s Fruit Farm Sang Lee Farms Wayside Market Agora Mattituck Marketplace Love Lane Market Nearby Restaurants and Bars: Red Rooster Bistro Touch of Venice Cutchogue Diner The North Fork Table & Inn Sophie’s Rest The Old Mill Inn Windamere Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 2,600 Additional guests above 12 will be subject to an additional persons fee of $100 per person per night. Suitability: Not handicap accessible. Primary renter must be at least 27 years old. Pet Policy: One hypoallergenic, non-shedding dog of 50 lbs or less is permitted for an additional $150.00 per night. Non hypoallergenic/shedding dogs or any dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $100.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. An additional guests fee of $50.00 per person per night may be required. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

24 Woodpink Drive

East Hampton, NY, US
4 Bedrooms 8 Guests
Sep 21 - 23
$744 night

WELCOME! Walk to Sammy’s Beach from this renovated home, perfect for families. Located in the NW Harbour, 12 minutes from East Hampton Village, Sag Harbour, both bay (child friendly) and ocean beaches (including Sammy’s and Main Beach, one of the best in the world!) and Wolffer Vineyard. 4 bd, 2.5 baths, plus outdoor/private shower. Master bed with king bed and en-suite bath. 3 bedrooms (two queen and one full). Guest bath with shower, powder room. Newly renovated and beautifully designed. Looking for a Quiet Retreat to relax in the Hamptons? Located in an amazing location in the East Hampton’s Northwest Woods is the perfect home where you can walk among leafy green treetops and nature daily, just one mile from the beach. Close to East Hampton Village, Sag Harbour, both bay (child friendly) and ocean beaches (includings Sammy’s and Main Beach, one of the best in the world!). 4 bedrooms, 2 full bathrooms, 1 powder room, 1 outdoor/private shower: Master bedroom with king bed and en-suite bathroom featuring a bathtub and shower. Three additional bedrooms (two queen and one full). Additional guest bathroom with shower, powder room and outdoor/private shower. Large in-ground pool (open) out door living and dining spaces with bbq. Pool can be heated for fee. Recently renovated and beautifully designed. Open concept living /dining with wood burning fireplace is perfect for families and entertaining. Close to hiking trails, golf, kayaking and outdoor activities. Close drive to Montauk. Central AC, wifi and smart TV with access to your Netflix and Spotify accounts. Registry 21-439 Check in on Friday or Saturday (June 23-Labor Day) I am available by text or just a phone call away. Welcome to East Hampton! #PinkwoodPlayhouse is located in an amazing location close to East Hampton Village, Sag Harbour, Montauk, both bay (child friendly) and ocean beaches (including Sammys and Main Beach, one of the best in the world!). Car is recommended. Friday or Saturday check-in in summer season (June 23-Labor Day)

16 Shorewood Dr

East Hampton, NY, US
3 Bedrooms 8 Guests
Sep 30 - Oct 3
$1,082 night

About the space SERENITY AT SHOREWOOD is the perfect setting of relaxed luxury with laid back beach vibes. Perfect for families or couples. Stunning cedar clad Midcentury Modern fully renovated from top to bottom to satisfy today’s luxury standards. Three luxurious bedroom suites, a large and fully equipped kitchen, soaring ceilings with skylights and open floorplan with oversized windows are highlights of this fabulous space located on a large landscaped lot in a quiet community. A 2023 Jeep Wrangler with removable top and East Hampton beach parking permit - the only way to park at most of the Hamptons beaches – is available (special terms apply, see details). We are 8 minutes away from the charming and lively Village of East Hampton; 3 minutes to the beautiful botanical gardens at Long House Preserve or Northwest Harbor (Sammy’s Beach is the perfect bay beach for a leisurely stroll or swim, popular with families because the bay waters tend to be calmer and warmer than the ocean); 10 minutes from world famous Main Beach, Two Mile Hollow or Egypt Lane ocean beaches; and 15 minutes to the historic whaling village of Sag Harbor or the beautiful Wolfer Estate vineyards and polo grounds and a little farther to Bridgehampton, Southampton and Montauk. Wake up to tranquil views of wide grass lawns and leafy green trees of East Hampton’s Northwest Woods, an enclave on a peninsula adjacent to East Hampton Village, surrounded by beautiful beaches and preserved woodlands for hiking, biking (2 adult bikes with helmets are included), and more. Jump in the heated pool for an invigorating swim or work on your tan poolside. After exploring the Hamptons, unwind in the hot tub, enjoy an outdoor movie, relax in the garden, or gather around the fire pit for smores. With a lower level game room for fun and games and cozy spaces to relax, our Hamptons escape invites unforgettable memories. The Space ★★PROPERTY HIGHLIGHTS★★ ✹ Serene location, on a leafy green private cut de sac, this corner property just shy of an acre is just 8 minutes from East Hampton Village and close to major outdoor activities from Cedar Point Park, Northwest Harbor, Hamptons beaches and the most popular restaurants and shops in the Hamptons! ✹ Heated inground pool with loungers, umbrellas and multiple seating areas ✹ Game room featuring foosball, classic Ms. Pacman table, classic board games, karaoke and lounge area with 75 inch Smart TV ✹ Sun splashed living room with soaring 20 foot ceilings, skylights, a wood-burning fireplace, opening to the deck and expansive back yard ✹ Spacious deck with outdoor dining, propane BBQ grill and seating area ✹ Multiple outdoor activities including Giant Four in a Row, Cornhole, and Jenga ✹ Fire pit area with comfortable custom Teak seating and lights creating a warm ambiance ✹ High-speed WiFi throughout ✹ Ample parking for up to 4 cars with easy access to all the Hamptons have to offer ✹ Pet-friendly, so your pets can be part of the fun (Up to 2) subject to prior approval and pet fee*** ✹ Ideal for couples (each bedroom has its own en suite bath) and families (a Pack ‘n Play, high chair and crib are provided for your little ones) ✹ New construction completed June 2023 *** If you bring pets please let us know in advance, pet fee required – see details below. ★★ LIVING ROOM ★★ Relax in the inviting living room, a perfect blend of minimalist decor and modern comfort. Whether you’re unwinding after a day exploring the Hamptons or enjoying a relaxing day at home, this space offers a warm and welcoming atmosphere. Double-height ceilings, oversized windows and skylights invite the sunshine in Large 65” Frame Smart TV to “Netflix and Chill” Stylish furnishings for your comfort Wood-burning fireplace for added warmth and ambiance Stylish powder room Retro vinyl station, perfect for spinning your favorite records as you relax. Sliding doors to the deck to enjoy your morning coffee for a serene morning experience Telescope to facilitate stargazing ★★ KITCHEN & DINING ★★ Channel your inner chef in the fully equipped kitchen, where high end stainless steel appliances, including wine refrigerator and five burner stove with pot filler and endless quartz countertops, make meal prep a joy and will be the perfect backdrop to show off your culinary creations on Instagram. Gather around the large bespoke surfboard inspired reclaimed oak dining table for memorable meals shared with loved ones. Prepare delightful libations at the built-in bar. Fully equipped kitchen with modern stainless steel professional grade appliances Sleek quartz countertops and essential cookware and serving ware plus basic spices and sundries Dining table seats 8, with additional seating for 2 at the kitchen breakfast bar Built-in bar to prepare and serve your favorite libations. ★★ DECK (MAIN LEVEL) OUTDOOR DINING ★★ Dine and relax outdoors on the spacious deck, where a seating area, dining table and propane BBQ grill invite you to enjoy meals surrounded by nature. The deck is perfect for both casual gatherings and special occasions. Great sightlines to the pool and back yard so you can keep an eye on everybody. Classic Midcentury Modern Woodard dining table with seating for 6 Couch and chairs to seat 5 Doors to deck are alarmed for safety Modern 3-burner BBQ propane grill Movie Projection Screen ★★ INGROUND POOL ★★ Open April 15 through October 15. Enjoy endless fun in the oversized inground pool (20x40). Surrounded by an expansive bluestone patio. The garden is surrounded by beautiful leafy green oak trees but the pool gets all day sun keeping it warm (however the pool can be heated for an additional fee to cover the energy cost). Relax by the pool on the chaise lounges and lounge chairs or have a poolside snack at the bistro tables. Enjoy a night swim in the glow of the underwater pool lighting. ★★ GAME ROOM (Lower Level) ★★ Discover endless fun in the game room, designed for both relaxation and entertainment. Whether it’s foosball, classic arcade games and board games or a round of karaoke, there’s something for everyone. Foosball Old school Ms. Pac Man arcade game table At least a dozen classic board games Karaoke setup for sing-along fun Sitting area with a large TV Popcorn machine and mini-fridge for refreshments ★★ FIRE PIT ★★ End your evening around the fire pit, where the soft glow of string lights creates a magical atmosphere. Make some s’mores memories! The comfortable seating makes it easy to relax and enjoy the cool Hamptons relaxation vibe in the evenings. Scupltural teak root table and 4 chairs Cafe lights adding a warm, inviting ambiance to the outdoor space Garden accent lighting Surround stereo that hooks up to your Sonos account The pool lights up too for the perfect night swim ★★ BEDROOMS ★★ Rest and recharge in beautifully appointed bedrooms, each offering comfort and style. With ample space and thoughtful touches, these rooms provide the perfect retreat after a day of adventure. Quality bed linens and towels will be provided. Plant based Shampoo, conditioner, shower gel and hand soap will also be provided. Bedroom 1 (Main Level): Queen bed, work space and Smart TV, with a luxurious ensuite tile and marble bathroom with curbless glassed entry to the oversized shower and lighted vanity mirror Bedroom 2 (Upper Level): King bed with private balcony, Smart TV and daybed that unfolds into a Queen bed to accommodate additional guests. Stunning ensuite marble bathroom with dual vanity, lighted vanity mirror, freestanding jetted tub, separate shower with curbless entry and discreet w/c room. Bedroom 3 (Upper Level): Queen bed, smart TV and crib or Pack ‘n Play if desired, and a stylish ensuite tile and marble bathroom with tub/shower combination, lighted vanity mirror and skylight. ★★PETS POLICY★★ We’re happy to welcome house-trained pets! There’s a $150 fee per pet (up to 2). if you plan to bring pets please make sure let us know in advance. Damage/extra cleaning required due to pets will incur an additional charge to be paid from security deposit. Please do not let pets relieve themselves on the grass (use mulched area) and clean up their poop. ★★BEACH CAR POLICY★★ Use of the Jeep is intended strictly to facilitate your going to the beach since there are no “beach passes” in the Hamptons (just beach permits – a sticker affixed to a specific car); it is NOT intended for you to drive around the Hamptons – please use your own vehicles for that. Mileage will be monitored and 20 miles per day is included, excessive mileage will incur a charge of $5 per mile, to be paid from security deposit. Use of the Jeep is at the sole risk of the driver and passengers. Driver shall be liable for any damage to the Jeep or any property damage or injury which may occur during such use (regardless of fault). The Jeep is only to be driven by experienced drivers over 25 years of age who have a valid license, no arrests or convictions for “driving while intoxicated” or similar offenses. Copies of drivers license must be provided prior to arrival and the Jeep may only be driven by those persons whose driver’s license has been so provided. ★★ Beach car is Memorial Day weekend through Labor Day. ★★ Guest access You will have the whole house and 1 acre of land to yourself to enjoy One supply closet is not accessible to guests. Other things to note ★★OTHER THINGS TO NOTE★★ The pet fee is a one-time, non-refundable fee that covers a cleaning post-checkout to prevent any allergy-related illness in the cabin. Pet-related damages or the need for excessive cleaning will be debited from the guest. Prior to check-in, you will be asked to sign a rental agreement. There is a $500 additional cleaning charge if there is any smell or evidence of smoking. Anyone found breaking these rules will be asked to leave without a refund. We provide a starter set of household supplies -dishwasher tablets, dishwasher soap, paper towels, toilet paper, shampoo, body soap, hand soap, and laundry tabs. Additional supplies can be purchased at: -IGA and Stop-and-Shop supermarkets (supermarket for everything, recommend pick up groceries on the way to the house, 8 mins from house) -Damarks Market (mom and pop grocery and deli). Smoothies, sandwiches and baked goods, 5 minutes from house). - Round Swamp Farm (small country market and farm stand with locally grown produce and prepared foods. 5 minutes from house) - Citarella Gourmet Market (full scale gourmet marketplace with delicious seafood. Offers delivery service to the house, 8 minutes from house) -Various Farmstands offering locally-grown produce, cheeses and even locally sourced seafood

Huckleberry Hideaway

Sag Harbor, NY, US
7 Bedrooms 14 Guests
Sep 20 - 23
$815 night

Huckleberry Hideaway Expansive Sag Harbor Estate with Pool, Tennis, Hot Tub, Close to Sag Harbor and Bridgehampton 7BR/8BA: private heated pool, hot tub, Har-Tru clay tennis court, finished lower level, office, Peloton bike, pool house, expansive outdoor dining area Welcome to this magnificent Sag Harbor estate, where luxurious living meets ultimate comfort. This stunning property features seven spacious bedrooms and eight pristine bathrooms, comfortably accommodating up to 14 guests. With its bright, airy interiors and multiple sitting and dining areas, this home is an idyllic retreat for families or large groups looking to escape daily life. Nestled on a serene private block, this estate promises peace and tranquility. The exterior of this property is nothing short of spectacular. Guests can enjoy total privacy while relaxing on the expansive deck, which boasts an outdoor dining area and a gas BBQ. The deck leads to a heated pool, perfect for refreshing swims, as well as a hot tub, fire table, and private tennis court for endless entertainment. For pickle ball enthusiasts, a portable net is at your disposal for a quick game. A charming pool house and multiple sitting areas provide ideal spots for evening cocktails. The vast yard offers plenty of space for outdoor activities, and ample free parking ensures convenience for all guests. Step inside and be captivated by the home’s open layout and abundance of natural light. The estate is equipped with modern conveniences such as WiFi, a washer and dryer, and central AC, ensuring a comfortable stay. The open living spaces flow seamlessly from the living room, with its cozy fireplace, to the elegant dining room and gourmet kitchen. The kitchen is a chef’s dream, featuring top-of-the-line appliances and a coffee maker. For those needing to work from home, there is a dedicated workspace, and the finished lower level includes an additional media area, office and Peloton bike. Each bedroom is a haven of comfort, outfitted with fresh linens and all the essentials you need for a restful night’s sleep. The bathrooms are elegantly designed, offering a spa-like experience with high-quality fixtures and finishes. Conveniently located close to Sag Harbor, Southampton, and Water Mill, this estate is perfect for exploring the best of the Hamptons. Golf enthusiasts will appreciate the proximity to Noyac Golf Club and The Bridge Golf Club, while nature lovers can explore the nearby Noyac County Park and Sag Harbor Beaches. Whether you seek relaxation or adventure, this expansive Sag Harbor estate is the perfect base for your Hamptons getaway. This property has a max occupancy of 14 Bedrooms Primary Bedroom: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet, Balcony/Deck Bedroom 4: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 5: One Double/Full Bed, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 6: One King Bed, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 7: One Queen Bed, Lower Level, Air Conditioning, Full Ensuite Bathroom, Standard Closet Bathrooms Primary Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Primary Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 4: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 5: Full Bath, First Floor/Main Floor, Ensuite, Shower/Tub Combo Bathroom 6: Full Bath, Lower Level, Ensuite, Jack & Jill, Shower Bathroom 7: Full Bath, Lower Level, Ensuite, Shower Pool House Bathroom 8: Full Bath, Pool House First Floor/Main Floor, Shower TVs Primary Bedroom: Streaming Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 4: Streaming Bedroom 5: Streaming Bedroom 6: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Tennis Court (Private), Fire Pit (Gas), Outdoor Shower (Hot + Cold Water), Tennis Equipment (Rackets, Balls), Beach Chairs, Beach Umbrella, Cooler, Fence Around The Yard, Fence Around The Pool, Private Pool (Outdoor, Heated), Hot Tub (Freestanding Hot Tub) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Blender, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Main Living Room, Media Room), Private Entrance, Parking, Smoke Detector, Essentials, Dishes and Silverware, Hair Dryer, Usable Fireplace (Wood-Burning), Smart TV, Garage, Carbon Monoxide Detector, Fire Extinguisher, Gym/Fitness Room (Stationary Bike) Special Features Please note the hot tub and tennis court are both available MDW through mid-October. If your booking falls outside of that time frame and you intend to use the hot tub or tennis court, please be sure to inquire if it will be available prior to booking. Location Nearby Beaches: Foster Memorial Town Beach (5 min drive) Circle Beach (5 min drive) Sagg Main Beach (15 min drive) Ocean Road Beach (15 min drive) Nearby Grocery Stores: Cromer’s Market (5 min drive) Sag Harbor Farmer’s Market (10 min drive) Schiavoni’s Market (10 min drive) Provisions Natural Foods Market (15 min drive) Nearby Restaurants and Bars: Bell & Anchor (3 min drive) MJ Dowling’s (5 min drive) Eds Lobster Bar (10 min drive) Estia’s Little Kitchen (10 min drive) The Dock House (10 min drive) DOPO La Spiaggia (10 min drive) Murf’s Backstreet Tavern (15 min drive) Murf’s Backstreet Tavern (15 min drive) The Beacon (15 min drive) Le Bilboquet (15 min drive) Sag Harbor Tavern (15 min drive) Other Location Information: Elizabeth A Morton National Wildlife Refuge (3 min drive) Sag Habor State Golf Course (20 min drive) Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 5,306 Suitability: Not handicap accessible. Primary renter must be at least 28 years old. Pet Policy: One hypoallergenic/non-shedding dog permitted for an additional $200.00 per booking. Non hypoallergenic/shedding dogs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $200.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: Hot Tub is only available for use from Memorial Day through approximately mid-October. If your booking falls outside of that time frame and you intend to use the hot tub, please be sure to inquire if it will be available prior to booking. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not the tennis court, outdoor furniture, and equipment will be available for use prior to booking. Note that the pool house is not available/usable from Oct-May as it is winterized for the season. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Charming Old Saybrook Cottage < 1 Mi to Beach

Old Saybrook, CT, US
4 Bedrooms 7 Guests
Oct 20 - 22
$285 night

Slip on your sandals and embrace the seaside when you book this Old Saybrook vacation rental! Ideally situated less than 3 miles from 4 different beaches, this 4-bedroom, 2-bath cottage is the ideal home base for your next trip to coastal Connecticut. Spend your days relaxing on the shores of Harvey’s Beach, or stay and enjoy the comforts of your home-away-from-home. In addition to its prime location, this property is also equipped with a full kitchen, in-unit laundry, and a private backyard. -- THE PROPERTY -- Family Friendly | Free WiFi | 2 Flat-Screen TVs Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Daybed | Additional Sleeping: Crib, Pack ‘n Play INDOOR LIVING: Finished basement w/ beanbag chairs, ceiling fans, window A/C unit, conversation areas OUTDOOR LIVING: Gas grill, furnished patio, deck KITCHEN: Stove/oven, refrigerator, toaster, microwave, dishwasher, Crockpot, coffee maker, blender, cooking basics GENERAL: Central air conditioning, washer/dryer, linens/towels, complimentary toiletries, hair dryer, high chair, iron/board, trash bags/paper towels FAQ: 2 steps required to access, 2 exterior security cameras (facing outward) PARKING: Driveway (2 vehicles), no garage access -- THE LOCATION -- BEACHES: Knollwood Beach (0.9 miles), Town Beach (2.2 miles), Harvey&#39;s Beach (2.6 miles), Great Hammock Beach (2.8 miles) RESTAURANTS: Fresh Salt (1.7 miles), Red Hen Restaurant (3.4 miles), Liv&#39;s Oyster Bar (3.6 miles), Little Pub Old Saybrook (4.1 miles) SHOPPING: Pearls &amp; Plaid (3.6 miles), Artisans Harbor (3.7 miles), Re-Unique Antiques (3.9 miles), So Chic the Fashion Lounge (3.9 miles) AIRPORTS: Bradley International Airport (59.0 miles), Rhode Island T.F. Green International Airport (71.9 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you&#39;ll never want to leave. You can relax knowing that our properties will always be ready for you and that we&#39;ll answer the phone 24/7. Even better, if anything is off about your stay, we&#39;ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While there are only 2 steps required to access the property, there are 3 steps down from the back deck - NOTE: Your safety matters. This property features 2 external security cameras: 1 camera is a Ring doorbell device with an exterior security camera facing the front outdoor entry, and 1 camera is in the garage, which is inaccessible to guests and faces the garage space. The cameras do not look into any interior spaces included with the rental. The cameras actively record video and sound when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed

Hilltop Hideaway

Sag Harbor, NY, US
5 Bedrooms 9 Guests
Sep 16 - 20
$1,449 night

Hilltop Hideaway Expansive Modern Sag Harbor Home with Private Heated Pool, Perfect for Families 4BR/4.5BA plus additional sleeping space: private heated pool, expansive yard, gas fireplace, sunroom, outdoor kitchen and dining with gas BBQ, office Welcome to this expansive Sag Harbor retreat, ideally situated just minutes from the charming villages of Southampton, Sag Harbor, and Bridgehampton. This beautiful home, with its open floor plan, offers four luxurious bedrooms, an additional sleeping space and four and a half pristine bathrooms, comfortably accommodating up to nine guests. As you step inside, you’ll be greeted by a spacious and bright interior, thoughtfully designed with multiple sitting and dining areas perfect for families and gatherings. This is more than just a place to stay; it’s an escape from the hustle and bustle of daily life, nestled on a beautiful private block. Outside, the expansive patio awaits, featuring an outdoor kitchen with a gas BBQ and a delightful dining area. It’s an ideal spot for enjoying al fresco meals and savoring the tranquility of your surroundings. The exterior of this home is a true oasis of relaxation and entertainment. Set on a sprawling acre of land, the property offers total privacy, ensuring a peaceful and secluded stay. The private heated pool is a highlight, inviting you to take a refreshing dip at any time of the day. The expansive patio is designed for outdoor living, with a well-equipped cooking area, a large dining table for memorable meals, and multiple sitting areas perfect for enjoying cocktails or simply soaking in the sun. The yard is spacious, providing plenty of room for outdoor activities and leisurely strolls. Ample free parking is available, making it convenient for all guests to come and go as they please. Step inside and embark on a tour of this stunning home. The open layout is accentuated by an abundance of natural light streaming through large windows, creating a warm and inviting atmosphere. Modern conveniences such as Wi-Fi, a washer and dryer, and central air conditioning are at your disposal, ensuring a comfortable and connected stay. The living spaces flow effortlessly from one to the next, with the living room featuring a cozy gas fireplace and plush seating. The dining room is perfect for family meals, and the gourmet kitchen is a chef’s dream, complete with top-of-the-line appliances, a coffee maker, and ample counter space for preparing delicious dishes. A dedicated work-from-home space and sunroom is also available, catering to guests who need to stay productive during their stay or just need a quite place to relax. The bedrooms in this Sag Harbor home are designed with comfort and tranquility in mind. Fresh linens and all the essentials are provided, ensuring a restful night’s sleep. Each bedroom offers a serene retreat, with ample storage and tasteful decor. The bathrooms are equally impressive, featuring modern fixtures and luxurious amenities. Whether you prefer a refreshing shower or a relaxing soak in the tub, you’ll find everything you need to unwind and rejuvenate. Located close to multiple golf courses, including The Bridge Golf Club, this home is a haven for golf enthusiasts. The beautiful Sag Harbor beaches, such as Foster Memorial Beach, are just a short drive away, offering endless opportunities for sunbathing, swimming, and water sports. The nearby villages of Southampton, Sag Harbor, and Bridgehampton are renowned for their charming restaurants, boutique shops, art galleries, and farm stands, providing plenty of options for dining, shopping, and exploring. Whether you’re looking to immerse yourself in the local culture or simply relax in the comfort of your private retreat, this Sag Harbor home is the perfect choice for your next getaway. This property has a max occupancy of 9 Bedrooms Bedroom 1: One Queen Bed, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2: One Double/Full Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Additional Sleeping Space: One Queen Bed, 2nd Floor, Air Conditioning Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 3: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 4: Full Bath, Lower Level, Shower Bathroom 5: Half Bath, First Floor/Main Floor TVs Bedroom 1: Streaming Bedroom 3: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fence Around The Yard, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Gas-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Private Entrance, Parking, Smoke Detector, Essentials, Wood Stove, Speaker System, Television (Main Living Room), Smart TV, Wine Fridge Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Other FAQ’s Backyard Fenced In: Yes Suitability: Primary renter must be at least 30 years old. Pet Policy: One dog of 25 lbs or less is permitted for an additional $250.00 per booking. Dogs over 25 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Millstone Villa | Home w/ Pool

Sag Harbor, NY, US
7 Bedrooms 14 Guests
Sep 30 - Oct 14
$1,236 night

Welcome to Millstone Villa a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Welcome to Millstone Villa, a refined seven-bedroom, ten bathroom estate nestled on nearly two acres in the heart of Sag Harbor. This cedar and stone residence blends timeless European elegance with clean modern lines, featuring expansive windows that fill the interiors with natural light. A grand entry foyer leads to generous living spaces detailed with custom finishes and premium materials, while the state-of-the-art kitchen is outfitted with Miele appliances, bespoke cabinetry, and a large island perfect for entertaining. Outside, enjoy an infinity-edge pool, private tennis court, and landscaped grounds designed for recreation and relaxation. Located just minutes from Sag Harbor Village, Long Beach, and local wineries, this estate combines sophisticated living with resort-style amenities, offering a rare opportunity to experience the Hamptons at its most elevated. To finalize your reservation, all guests must pass a mandatory third-party screening process. Pet Policy: Pets are not allowed at this property. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. The pool is open seasonally (2026 Pool closure date: September 28th). It is professionally cleaned and chemically balanced weekly; however, as an open-air pool, natural debris between service visits is normal. A skimmer net is provided for your convenience, and our team is always happy to assist if needed. Pool heating is available for an additional $75/night and is designed to maintain temperatures up to approximately 82–84°F under normal operating and weather conditions. Outdoor pool temperatures may vary based on weather, usage, and other external factors. While we make every effort to ensure the heater is functioning properly, pool heating cannot be guaranteed at a specific temperature at all times. In the unlikely event the heater is unavailable due to a mechanical or service issue, pool heating fees will be refunded. Utilities, including pool heating, are billed separately for stays over 14 nights. The tennis court is now open and available for guest use. As a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property. Monthly Housekeeping Policy: For all reservations with stays of 60 nights or longer, a full mid-stay cleaning by our housekeeping team is required every 30 days. The required mid-stay cleaning fee(s) will be invoiced immediately prior to the service and upon coordination of a suitable date and time for the cleaning to take place. Security deposit Stays up to 179 nights: $5,000 credit hold Stays of 180 nights or longer: Cash security deposit equal to one month’s rent

Blue Jay Villa | Luxe Home with Pool

East Hampton, NY, US
7 Bedrooms 14 Guests
Sep 28 - Oct 1
$850 night

Welcome to Blue Jay Villa, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Step into Blue Jay Villa, a luxurious home located in East Hampton. This newly built 7-bedroom, 8-bathroom residence offers over 9,000 square feet of thoughtfully designed living space on a private 1.1-acre lot. Built from durable concrete and powered by a full solar array, the home is both energy-efficient and built to last. Floor-to-ceiling glass sliders and oversized windows create a bright, open feel and connect the interior with the surrounding landscaped grounds. The main level features large-format Italian porcelain tile and natural stone, while wide-plank European oak floors add warmth upstairs. At the center of the home is a custom Arc Linea kitchen with fossil-finish oak cabinetry, Grigio Argentino marble countertops, high-end Miele appliances, and a separate prep kitchen. The spacious great room opens directly to a 20’ x 40’ heated gunite pool, pool house, and outdoor kitchen, ideal for indoor-outdoor living. Each bedroom is generously sized and includes refined finishes. The primary suite features a spa-style bathroom with Carrara marble, Italian fixtures, and a clean, modern design. Resort-style features including lush garden terraces complete this marvellous retreat. This exquisite residence is a rare mix of high-end design, smart systems, and everyday comfort, designed for privacy, performance, and style. To finalize your reservation, all guests must pass a mandatory third-party screening process. Pet Policy: Pets are allowed with owner approval and a one time $150 charge. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. As a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property. The pool is open seasonally and will close on October 16, 2026. It is professionally cleaned and chemically balanced weekly; however, as an open-air pool, natural debris between service visits is normal. A skimmer net is provided for your convenience, and our team is always happy to assist if needed. Pool heating is available for an additional $75/night and is designed to maintain temperatures up to approximately 82–84°F under normal operating and weather conditions. Outdoor pool temperatures may vary based on weather, usage, and other external factors. While we make every effort to ensure the heater is functioning properly, pool heating cannot be guaranteed at a specific temperature at all times. In the unlikely event the heater is unavailable due to a mechanical or service issue, pool heating fees will be refunded. Utilities, including pool heating, are billed separately for stays over 14 nights. The home may occasionally be subject to a brief broker or real estate showing during your stay, as the property is currently on the market. Showings may require a minimum of approximately 2 hours’ notice and are typically brief. Guests may remain in the home during a scheduled showing if they prefer. Open houses might also be required, and in those cases, guests will be asked to vacate the property. Please consider this before booking this specific property. Cleaning & Maintenance Fees: Turnover Clean: $1,495 Light Mid-Stay Clean: $630 Mid-Stay Clean (with Laundry): $1,035 Refresh Clean: $575 Pool Heating (per night): $75 Security deposit Stays up to 179 nights: $5,000 credit hold Stays of 180 nights or longer: Cash security deposit equal to one month’s rent

Secluded Getaway in East Hampton with Private Pool and Hot Tub

East Hampton, NY, US
3 Bedrooms 7 Guests
Sep 21 - 24
$324 night

Ober Oaks Gorgeous East Hampton Hideaway with Privacy and Full Amenity Suite 3BR/3.5BA, Modern Design with Hot Tub, Pool and Steps from the Water, Smart TV This stunning three bedroom, three and a half baths vacation rental home is your Hamptons hideaway. With enough space to comfortably sleep seven, this 2,600 sq ft abode offers a modern and tastefully furnished interior, a gourmet kitchen with stainless steel appliances, a balcony, and an unbeatable outdoor entertainment area with a deck, grill, private hot tub, outdoor shower, wooden cold plunge tub, heated pool, cozy basket swing and supersized hammock. Whether you’re in town to soak up the sun at the private pool or shop in the Hamptons, this is the perfect East Coast escape nestled in the deep woods of Springs Hamlet on a private, secluded acre off an exclusive cul-de-sac and just 350 yards to the harbor. This cul-de-sac has exclusive access to a small beach fronting Three Mile Harbor. This beach is accessed via a short walk through the woods at the end of the block. This beach is on an access waterway to Three Mile Harbor, and is a lovely spot with beautiful sunsets. Any guest on our cul-de-sac will likely enjoy a visit to this beach, and those who enjoy water sports like Stand-Up-Paddling will definitely enjoy the easy access to the placid waters of Three Mile Harbor. This property has a max occupancy of 7 Bedrooms Bedroom 1: One Queen Bed, One Twin Single Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Cable TV, Standard Closet Bedroom 2: One Child Bed, One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Cable TV, Standard Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Cable TV, Standard Closet, Balcony/Deck Bathrooms Bathroom 1: Half Bath, First Floor/Main Floor Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower, Tub TVs Bedroom 1: Cable Bedroom 2: Cable Bedroom 3: Cable Outdoors & Pool/Spas Deck/Patio, Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Outdoor Shower (Hot + Cold Water), Beach Chairs (2 Chairs), Beach Umbrella, Fence Around The Yard, Balcony, Swing Set, Kayak/Canoe, Private Pool (Outdoor, Heated, Freshwater), Hot Tub (Freestanding Hot Tub) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Gas-Burning, Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Dishwasher, Microwave, Coffee (Pot, Other), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Main Living Room, Kitchen), Smart TV, Speaker System (Bluetooth Speaker), Sauna, Parking (6 Cars In Driveway), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Game Room, Laptop-Friendly Workspace, Pots and Pans, Essentials, Private Entrance, Gym/Fitness Room (Weight Training Equipment, Stretching / Yoga Mat), Ping Pong Table, Privacy (Completely Private) Location Nearby Beaches: This cul-de-sac has exclusive access to a small beach fronting Three Mile Harbor. This beach is accessed via a short walk through the woods at the end of the block. The public recreation area of Maidstone Park is nearby and an easy walk too. Nearby Grocery Stores: Damark’s Market is about a mile and 1/2 west on Three Mile Harbor Rd. An IGA and Citarella are about 3 miles. Nearby Restaurants and Bars: The very popular Bostwicks on the Harbor restaurant is an easy walk through the same woods as the beach and overlooking the harbor with magnificent sunsets. This property is also within walking distance of the renowned S S Restaurant and the Sunset Harbor Waterfront Restaurant, offering guests a perfect blend of fine dining and coastal charm right at their doorstep. Other Location Information: Ober Oaks is nestled in a serene acre of woods. The block has only 10 houses, each of which occupy an acre. This is a quiet neighborhood and peaceful street. Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 2,500 Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: One dog of 75 lbs or less is permitted. Dogs over 75 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $80.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool & Hot Tub Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Vacation Rentals in Greenport by Amenities & Features

Get to Know Greenport

Greenport, New York, is a charming maritime village that beckons travelers with its picturesque waterfront, rich maritime history, and vibrant community spirit. Located on the North Fork of Long Island, Greenport is a delightful blend of old-world charm and modern sophistication, making it an ideal getaway for those seeking a serene coastal experience. The village's maritime heritage is a central part of its allure. Visitors can explore the Greenport Historic District, where 19th-century architecture provides a glimpse into the village's past as a whaling and fishing port. The East End Seaport Museum and Marine Foundation offer insights into the local maritime history and the area's rich ecosystem, while the nearby Railroad Museum of Long Island celebrates the region's railroading history. Greenport's waterfront is a focal point for activity, with the Mitchell Park Marina and Carousel providing family-friendly entertainment. The antique carousel, with its hand-carved and painted horses, is a nostalgic treat for all ages. The park also hosts outdoor concerts and events, adding to the village's lively atmosphere. For oenophiles, Greenport is a gateway to some of Long Island's finest vineyards and wineries. The surrounding North Fork region is renowned for its award-winning wines, and visitors can indulge in tastings and tours amidst the scenic vine-covered landscapes. The village's dining scene is a testament to its coastal location, with an array of restaurants serving fresh, locally-sourced seafood. From casual dockside eateries to upscale dining establishments, there's something to satisfy every palate. The Greenport Farmers Market also offers a taste of local produce and artisanal goods, perfect for those who appreciate farm-to-table freshness. Outdoor enthusiasts will find plenty to do in and around Greenport. Sailing, fishing, and kayaking are popular activities, allowing visitors to experience the beauty of Peconic Bay firsthand. For those who prefer land-based adventures, the area's beaches, nature preserves, and bike trails offer ample opportunities for exploration. Greenport's small-town charm is complemented by its boutique shops and galleries, where visitors can find unique gifts, art, and handcrafted items. The village's walkability invites leisurely strolls through its quaint streets, making it easy to discover the hidden gems that make Greenport so special. In essence, Greenport, New York, is a destination that offers a peaceful retreat with a touch of nautical nostalgia, local flavors, and natural beauty. It's a place where visitors can slow down, savor the moment, and create lasting memories by the sea.
Greenport, New York, situated on the North Fork of Long Island, experiences a climate that is generally characterized by distinct seasons, with comfortable summers, cold winters, and a relatively moderate spring and fall. Summer in Greenport, from June to August, is the peak tourist season, with temperatures averaging in the high 70s to low 80s Fahrenheit. The humidity can be high, but the proximity to the water often brings a refreshing breeze that makes the climate quite enjoyable for beach-going, boating, and exploring the local vineyards. Precipitation is moderate, with occasional thunderstorms that are typically brief. Autumn, from September to November, sees a beautiful transformation as the foliage changes color, creating a picturesque backdrop for the town's maritime charm. Temperatures start to cool, ranging from the 60s in early autumn to the 50s and below as winter approaches. This season is less humid and has lower precipitation, making it a favorite for those who enjoy outdoor activities without the summer crowds. Winter, from December to February, is cold with temperatures often hovering around the freezing mark. Snowfall can vary, but Greenport generally experiences a few snowstorms each season, which can add a quaint, wintry appeal to the historic seaport village. While it's off-peak for tourists, the winter season offers a quiet, serene atmosphere with fewer visitors. Spring, from March to May, is a time of renewal in Greenport as the temperatures gradually warm up, ranging from the 40s to the 60s by late spring. The humidity is low, and while April showers are common, they bring forth the blossoming of local flora, making it a beautiful time to witness the awakening of vineyards and gardens. The most popular weather conditions are found in the late spring to early fall, when the temperatures are warm but not too hot, and the humidity is manageable. Late spring offers the added benefit of fewer tourists and the beauty of the season's blooms. The fall, with its crisp air and vibrant foliage, is also a particularly pleasant time to visit for those looking to enjoy outdoor activities and the region's natural beauty without the summer heat.
Greenport, New York, is a charming village on the North Fork of Long Island that offers a delightful array of cultural activities for travelers with a love for the arts, history, and local customs. This picturesque maritime village, with its quaint streets and stunning waterfront, is a hidden gem for those seeking a cultural retreat. Begin your exploration at the East End Seaport Museum, located in the historic 1840s railroad station on the waterfront. The museum offers a fascinating glimpse into Greenport's maritime heritage, with exhibits on the area's rich history of fishing, shipbuilding, and oystering. The museum also hosts the annual Maritime Festival, a celebration of the village's nautical past with classic boat displays, live music, and local food. Art enthusiasts will find solace in the numerous galleries dotting the village. The South Street Gallery and Greenport Harbor Brewing Company both showcase works by local artists, ranging from paintings and sculptures to mixed media pieces. These venues often host opening receptions and artist talks, providing an intimate setting to engage with the vibrant local art scene. For live music, Greenport has a lively scene, especially during the summer months. Mitchell Park's outdoor amphitheater is a popular venue for concerts and performances, offering everything from jazz to folk music against the backdrop of the harbor. Local bars and restaurants also feature live bands and solo artists, creating a festive atmosphere for enjoying the village's nightlife. History buffs will appreciate the 1920s carousel in Mitchell Park, a beautifully restored piece of Americana that offers rides to visitors of all ages. The nearby Greenport Village Historic District is a walkable area with well-preserved homes and buildings that tell the story of the village's development from a whaling port to a modern community. Greenport's local customs are best experienced through its culinary offerings. The village is surrounded by vineyards, making it an excellent spot for wine tasting. Local seafood is a staple, and visitors can indulge in freshly caught fare at the many restaurants and the Greenport Farmers Market, which also features local produce and artisanal goods. Throughout the year, Greenport hosts a variety of events that celebrate local culture, such as the Shellabration festival, which honors the area's shellfish with tastings and chef demonstrations. The village's walkable layout, friendly locals, and relaxed pace make it an ideal destination for cultural enthusiasts looking to immerse themselves in the arts, history, and traditions of a unique coastal community.
Greenport, New York, is a charming seaside village that offers a delightful escape for families and a treasure trove of activities for children. Nestled on the North Fork of Long Island, this picturesque destination is perfect for those looking to combine relaxation with family fun. Begin your adventure at the Antique Carousel, located in Mitchell Park. This historic 1920s carousel is a magical experience for kids, with its hand-carved and painted horses. The park itself is a great spot for a family picnic and offers plenty of space for children to play. For young marine enthusiasts, the East End Seaport Museum provides an educational journey through the maritime history of the area. Kids can learn about the local fishing industry, lighthouse history, and even see a real blacksmith at work. The museum often hosts children's workshops and storytelling sessions, making it an engaging experience for little ones. Take a stroll to the Greenport Harbor Brewing Co., which is surprisingly kid-friendly during the day. While parents sample local brews, children can enjoy the quirky art installations and the laid-back atmosphere. For outdoor lovers, Greenport offers access to beautiful beaches such as Orient Beach State Park, where families can swim, kayak, and explore the marine life in the clear waters. The park also has a playground and picnic areas, making it an ideal spot for a day out with the kids. Railroad enthusiasts, both young and old, will enjoy a visit to the Railroad Museum of Long Island. Here, children can explore historic train cars, model train displays, and learn about the region's railroad history. The museum often hosts special events, including train rides on their miniature railroad, which are a hit with the kids. If you're visiting during the fall, Harbes Family Farm offers a fantastic array of kid-friendly activities, including pumpkin picking, hayrides, and a corn maze. The farm also has barnyard animals that children can meet and feed. Finally, no trip to Greenport is complete without a boat tour. Peconic Star Fleet offers family-friendly excursions that allow you to enjoy the scenic beauty of the Peconic Bay. Keep an eye out for local wildlife, including seals and a variety of birds. Greenport, with its mix of educational attractions, outdoor activities, and family-oriented fun, is a destination that promises to keep children entertained and create lasting memories for the entire family.
Greenport, New York, is a charming village on the North Fork of Long Island, offering a serene escape with its maritime heritage and natural beauty. For outdoor enthusiasts and nature lovers, Greenport serves as a gateway to a variety of experiences that celebrate the great outdoors. One of the main attractions is the Greenport Conservation Area, where visitors can explore over 50 acres of scenic trails that meander through forests, meadows, and wetlands. The area provides a habitat for a diverse array of wildlife, and the trails offer stunning views of the Long Island Sound and Shelter Island, making it a perfect spot for hiking, bird-watching, and nature photography. For those who love the water, Greenport's location on the Peconic Bay means there are ample opportunities for kayaking, paddleboarding, and sailing. The calm waters are ideal for all levels of paddlers, and the scenic coastline dotted with beaches and coves is waiting to be explored. Boat tours and fishing charters are also available for those looking to venture further out into the waters and perhaps catch a glimpse of the local marine life. Wine enthusiasts can enjoy the natural splendor of the area while visiting the numerous vineyards and wineries that dot the North Fork landscape. Many of these establishments offer outdoor tastings and tours, allowing guests to sip on local wines while surrounded by picturesque vineyards. For a unique outdoor experience, visitors can take a short ferry ride to Shelter Island, a tranquil oasis with unspoiled natural beauty. Here, the Mashomack Preserve covers a third of the island and features over 2,000 acres of tidal creeks, mature oak woodlands, fields, and freshwater marshes. The preserve's extensive trail system invites nature walks and wildlife observation. Lastly, the Horton Point Lighthouse, built in 1857, stands as a historic beacon with a park that provides a peaceful setting for picnicking and relaxation. The lighthouse itself offers panoramic views of the Sound from its tower during the summer months. Greenport's blend of maritime history, vineyard-dotted landscapes, and coastal beauty creates a perfect backdrop for outdoor activities and nature exploration. Whether you're trekking through conservation areas, paddling on the bay, or enjoying the tranquility of a vineyard, Greenport, New York, is a delightful destination for those seeking to connect with nature.
Greenport, New York, is a charming village on the North Fork of Long Island, known for its maritime history, vineyards, and beautiful beaches. This quaint destination is accessible by various modes of transportation, catering to the preferences of different travelers. Many visitors arrive in Greenport via the Long Island Rail Road (LIRR), which offers a scenic journey from New York City's Penn Station to the Greenport station, located right in the heart of the village. The train ride provides a relaxing transition from the bustling city to the serene landscapes of Long Island's wine country. For those who prefer to drive, Greenport is accessible by car and is approximately a two-hour drive from New York City, depending on traffic. This option offers flexibility and the opportunity to explore the picturesque towns and wineries along the route at your own pace. Once in Greenport, getting around is quite convenient. The village itself is very walkable, with most restaurants, shops, and attractions such as the Greenport Carousel and the Maritime Museum within easy walking distance. The compact nature of the downtown area makes it ideal for leisurely strolls, allowing visitors to soak in the local charm and coastal atmosphere. For exploring the wider North Fork region, visitors can use the Suffolk County Transit bus service, which connects Greenport to other towns and points of interest. Additionally, bike rentals are available for those who wish to enjoy the scenic country roads and the area's natural beauty. During the summer months, the Shelter Island Ferry operates from Greenport, providing a quick and picturesque way to visit Shelter Island. This is a popular day trip for those looking to enjoy the island's beaches, nature preserves, and laid-back vibe. Boating enthusiasts can also arrive in Greenport by docking at one of the several marinas in the village, making it a popular stop for those sailing the Peconic Bay. In summary, Greenport offers a variety of transportation options suitable for a relaxing getaway. Its walkable village center and easy access to surrounding attractions make it a delightful destination for those looking to experience the slower pace and natural beauty of Long Island's North Fork.

Greenport FAQs

Greenport, located on the North Fork of Long Island, offers a variety of activities for visitors. You can explore the charming downtown area with its boutiques, art galleries, and restaurants. The Maritime Village is home to the Greenport Carousel, a historic merry-go-round. Wine enthusiasts can enjoy tastings at local vineyards. Outdoor activities include boating, fishing, and visiting beaches like Orient State Park. The Greenport Harbor Brewing Company is a great stop for craft beer lovers. Additionally, the Shelter Island ferry provides easy access to more adventures.
The best time to visit Greenport is during the late spring to early fall, from May to October, when the weather is warm and all the shops, vineyards, and attractions are open. Summer is peak season, offering the full experience of the town's maritime charm, though it can be more crowded.
Yes, Greenport hosts several events throughout the year. The Maritime Festival in September celebrates the village's nautical heritage with parades, boat tours, and live music. The Greenport Shellabration in December is a popular event for seafood lovers, featuring local shellfish and wine pairings.
Greenport boasts a diverse dining scene with options ranging from casual eateries to upscale restaurants. Seafood is a highlight, with many places serving fresh, locally caught fish and shellfish. There are also a number of spots offering international cuisines, farm-to-table experiences, and cozy cafes.
Absolutely, Greenport is very family-friendly. There are activities suitable for all ages, including the antique carousel in Mitchell Park, beaches for swimming, and ice cream shops. The village is walkable and safe, making it easy for families to explore.
Greenport is accessible by car, bus, or train. The Long Island Rail Road (LIRR) offers a direct route from New York City to Greenport. By car, it's about a 2-hour drive from NYC without traffic. Hampton Jitney and Suffolk County Transit also provide bus services to the area.
Yes, Greenport offers a range of accommodations, from luxury boutique hotels and quaint bed and breakfasts to more affordable inns and motels. There are options to suit various budgets and preferences, but it's advisable to book in advance, especially during the summer months.

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