Eastham, MA Vacation Rentals

14429 - Herring Brook Haven: 2025 Remodel! Walk to Pond, 2 Min Drive to Beach! If you thought a trip to this spacious retreat couldn’t get any better, over $300,000 of interior and exterior renovations were completed in 2025 and are ready to welcome guests! These include a brand new kitchen, the addition of 2 full bathrooms, renovation of the 2 existing bathrooms, brand new decking, interior and exterior painting, trim upgrades, and a revamped mini-split AC system. Escape to the quintessential Cape Cod retreat where every member of the family is invited to bask in the beauty of land and sea. Nestled within the tranquil embrace of Eastham, this expansive family home promises a week of relaxation and adventure, whether you’re lounging by the pristine shores of Herring Pond or exploring the scenic trails of the National Seashore.<br><br>Situated just a stone’s throw from the crystalline waters of Herring Pond, one of Cape Cod’s deepest and most pristine ponds, outdoor enthusiasts will delight in the array of recreational opportunities at their fingertips. <br><br>If you can pull yourself away from the comfort of the newly upgraded home, grab your bike and set off on an exhilarating journey along the rail-trail or meander through the quiet back roads, soaking in the natural splendor of the surrounding landscape.<br><br>Set upon a sprawling lot enveloped in privacy, this remarkable vacation home offers three levels of spacious living, ensuring ample room for everyone to spread out and unwind. Ascend to the top level (2nd floor), where a welcoming open-concept layout awaits, boasting a spacious kitchen (newly renovated), dining area, living space bathed in natural light, and half bathroom. Step out onto the expansive deck (newly re-constructed), where panoramic views of the enchanting natural landscape and glimpses of the famous First Encounter marshlands await. There is also a game room located above the garage and accessible via the exterior stairs/deck.<br><br>Back on the first floor, retreat to one of the three spacious bedrooms, each thoughtfully appointed to ensure a restful night’s sleep. Discover a queen bedroom with an en suite full bath room, a bedroom with two twin beds, and another room with a bunk bed (twin over full). There level also includes an additional full bathroom. Descend to the professionally finished basement, where a private laundry room awaits alongside two separate sleeping areas, furnished with a queen bed and a twin bed and a newly constructed bathroom. <br><br>From scenic vistas to ample space for gatherings, this fantastic vacation home offers the perfect blend of comfort, convenience, and coastal charm for an unforgettable Eastham getaway.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $45/night per dog)<br>-3 Floors: 1st Floor, 2nd Floor, Ground Floor<br>-Sleeps 8<br>Bedrooms<br>-Total: 4<br>-1st Floor Master Bedroom: 1 Queen Bed w/ en suite full bathroom<br>-1st Floor Bedroom: 2 Twin Beds<br>-1st Floor Bedroom: 1 Bunk bed (1 Twin Bed and 1 Full Bed)<br>-Ground Floor Bedroom: 1 Queen Bed and 1 Twin Bed (Semi-Private Sleep Area)<br>Bathrooms<br>-Total: 3.5<br>-1st Floor: Full Bathroom w/ Shower<br>-1st Floor: Full Bathroom w/ Shower (en suite Queen Bedroom) <br>-2nd Floor Half Bathroom<br>-Ground Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities:<br>-Split A/C <br>-Cable TV<br>-WiFi<br>-Washer/Dryer in basement<br>-Tub<br>-Outdoor shower<br>-Private yard<br>-Gas grill<br>-Game Room<br>-Please note outdoor amenities are available seasonally <br>-There is parking for a maximum of 6 cars<br>-1-minute walking distance to the pond!<br>-Sheets and bath towels provided with beds made upon arrival<br>-Cleaned with hospital grade disinfectant<br>C0414890860

14443 - The Surf Lodge: Expansive Home by Rail Trail Near Beaches! Our charming home is the right choice for a group looking to enjoy a quintessential Cape Cod getaway. Return home from one of the area’s many bayside or ocean beaches, rinse off in the outdoor shower, whip up your favorite summer cocktail and sip it on either the back deck, or lovely three-season porch. Enjoy making meals in the large kitchen with tons of prep space. New floors have just been installed for this season. Unlike many Cape rentals, this home has comfortable beds that will be made with fresh linens upon your arrival, and great Game Room with adult size billiards table for hours of family fun. Explore the area by renting some bikes and hopping on the bike trail, taking a day trip to Provincetown, or enjoying the National Seashore. There’s so much to explore on the Outer Cape, and having this adorable cottage with room for 12 (plus the dog) to call home base will ensure you have a great vacation! <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 12<br>-2 Floors<br>-1st Floor Master Bedroom: 1 King Bed<br>-1st Floor Bedroom #2: 3 Twin Beds<br>-2nd Floor Bedroom #1: 1 Queen Bed + 1 Twin Bed<br>-2nd Floor Bedroom #2: 2 Queen Beds<br>-Bathrooms<br>-Total: 3<br>-Ground floor full bath<br>-First floor full bath<br>-Second floor full bath<br>-Central A/C<br>-TV w/ Streaming<br>-WiFi<br>-Washer/Dryer <br>- New floors <br>-Outdoor Shower<br>-Deck<br>-Three Season Porch<br>-Gas Grill<br>-Game Room - Billiards Table<br>-Abutting Cape Cod Rail Trail<br>-Linens and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0424910860

Gorgeous 4 bedroom 2 bath home with deeded neighborhood path to sandy beach at Herring Pond. House is at the end of the street in a quiet neighborhood. Spacious deck overlooks patio with fire pit. Outdoor furniture: dining table for 6. Lounge chairs. Beach Chairs. Large flat screen smart tv in living room for your streaming pleasure. (no cable). Close to the Cape Cod Rail Trail for biking. Beautifully furnished and a well stocked kitchen. **Blankets and Pillows are provided, but you will need to bring or rent sheets and towels**

14525 - Sunlight Stay: 2 Miles to Coast Guard Beach! Welcome to your serene retreat in Eastham! This inviting four-bedroom, two-and-a-half-bathroom vacation home is perfect for families looking to unwind and explore Cape Cod. Inside, discover a spacious living room with a plush leather couch, offering an ideal spot for morning coffee and board games. The smart TV in the other family room is ready for cozy movie nights. The home’s open dining area is perfect for family meals prepared in the fully-equipped kitchen.<br><br>Ascend the spiral staircase to the second floor suite where you’ll find a queen and full bed with their own private bathroom. Up a second staircase, you’ll find the 3 remaining bedrooms on the second floor. <br><br>Outside, a large, private backyard invites you to enjoy the fresh Cape air. Fire up the grill on the back patio, gather around the wood fire pit for tales under the stars, or rinse off in the outdoor shower after a day at the beach. Situated less than three miles from the stunning Nauset Light, and Coast Guard Beaches, and just moments from local favorites like Mac’s Market and Kitchen, Brickhouse Seafood & Grill, and Red Barn Pizza, this location is a haven for foodies and beach lovers alike. Whether you’re lounging in the backyard or exploring Eastham’s pristine beaches, this home provides everything you need for a quintessential Cape Cod experience. Don’t miss your chance to create unforgettable memories—book your tranquil Cape Cod escape today!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>Bedrooms<br>-Total 4<br>-2nd Floor Bedroom: 1 Queen Bed<br>-2nd Floor Lofted Bedroom: 1 Full Bed + 1 Twin Bed w/ ensuite Full Bathroom<br>-2nd Floor Bedroom: 1 Twin Trundle<br>-2nd Floor Bedroom: 1 Twin Trundle<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Half Bathroom<br>-2nd Floor: Full Bathroom w/ Shower (en suite Loft Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub Combo<br>Other Amenities <br>-Bedrooms Air Conditioned via Mini-Splits and window AC<br>-WiFi<br>-Smart TV<br>-Washer/Dryer <br>-Propane Grill<br>-Fire pit (gas)<br>-Outdoor Shower<br>-Indoor Fireplaces are not for guest use (fines remitted) <br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 4 cars maximum<br>-C0066750860

14457 - Emerald on the Cove: Seaside Retreat w/ Private Beach Landing! Stunning views of breathtaking natural beauty, peace and quiet with seabirds in the distance, and a waterfront home to enjoy it all in is waiting in Eastham, Cape Cod. Your favorite vacation spot is ready for you, at Emerald on the Cove! As you walk down the path on the side of the home, your draw will drop when you see the views of Nauset Estuary right below your front door, and the Atlantic Ocean off in the distance.<br><br>Step through the cover deck, and enter into a lovely kitchen, with retro styled forte refrigerator, and views of the water through the glass door. Stepping further into the home, you can enjoy your meal at the funky-colored dining table, or take a seat in the sitting area with the porch door open letting the sea breeze in. Tucked in the corner, with continued views of the water, a living room with comfy couch and gas fireplace is a great place to relax, chat, or throw a movie on to the wall mounted TV.<br><br>The home’s three bedrooms are at the rear of the home, two with a queen bed, and a fun kids room with bunk bed, continuing the bright color theme of the house. <br><br>Surely you’re going to want to spend a lot of time on the back porch, with outdoor sectional, and a hot tub overlooking the saltwater below. Head down the steps, 10 ft from your back porch, where you can launch kayaks or stand up paddle boards into the marsh. The salt water is sure to be refreshing on hot summer days<br><br>Other amenities include an outdoor shower, picnic table and chairs to enjoy meals under the sun, and a central A/C. Relax in style and enjoy the calmness Cape Cod brings to your vacation, at Emerald on the Cove!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 6<br>-Single Floor<br>-3 Bedroom & 1 Bathroom<br>Bedrooms<br>-Total 3<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Twin Bunk Bed<br>Bathrooms<br>-Total 1<br>-1st Floor: Full Bathroom with Iron-Claw Tub and Shower<br>Other Amenities<br>-Central A/C<br>-Smart TV with Streaming<br>-WiFi<br>-Hot Tub<br>-Private Beach Landing<br>-Two Kayaks and Stand Up Paddle Boards with Lifejackets <br>-Private Deck with Outdoor Lounging<br>-Patio Furniture and Picnic Table<br>-Propane Grill<br>-Gas Fireplace <br>-Waterfront<br>-Water Views of Nauset Estuary and the Atlantic Ocean<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0429700860

14471 - Salt Water Sabbatical: Heated Saltwater Pool Hot Tub! In the woods of Eastham, a stunning oasis awaits. With your own heated in-ground saltwater swimming pool and hot tub, you’ll be soaking up the sun and salt water at the Salt Water Sabbatical. <br><br>The backyard is designed for long summer days and memorable evenings, featuring a private heated saltwater pool, hot tub, spacious stone patio, outdoor dining area, propane grill, fire pit, and outdoor shower. Whether you’re enjoying a morning swim, unwinding in the hot tub after the beach, or gathering around the fire pit under the stars, there’s no shortage of ways to enjoy your time outdoors.<br><br>When you’re ready to explore, you’ll be just minutes from both the Cape Cod Bay beaches and the Cape Cod National Seashore, making it easy to experience both the calm tidal flats and the Atlantic shoreline. Spend the day swimming, beachcombing, or watching the sunset before returning home to your own private oasis.<br><br>Inside, the bright, open layout is designed with comfort in mind. The first floor features a spacious living room with a Smart TV and home theater sound system, a beautifully appointed kitchen with a large center island, a half bath, laundry, and a queen primary suite with an en suite full bathroom. Upstairs, you’ll find three additional bedrooms—two with queen beds and one with two twin beds—along with two full bathrooms, providing plenty of space for everyone to spread out.<br><br>Whether your perfect vacation includes pool days, beach adventures, or simply enjoying the peaceful surroundings, Salt Water Sabbatical offers everything you need for an unforgettable Eastham escape. Book your stay today and experience the best of the Outer Cape.<br><br>Home Details:<br>-No Pets (Fines Remitted)<br>-Sleeps 8<br>-2 Floors (1st + 2nd Floor)<br>-2,400 Sq. Ft. <br>Bedrooms<br>-Total 4<br>-1st Floor: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor: 1 Queen Bed w/ Jack and Jill Full Bathroom<br>-2nd Floor: 2 Twin Beds w/ Jack and Jill Full Bathroom<br>Bathrooms<br>-Total 3.5<br>-1st Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo (Jack and Jill style)<br>-1st Floor: Half Bathroom<br>Other Amenities<br>-Central A/C<br>-WiFi<br>-Smart TV <br>-Washer and Dryer (1st Floor)<br>-Propane Grill<br>-Fire Pit<br>-Patio with Outdoor Dining and Lounging<br>-Outdoor Shower<br>-Private Heated Saltwater Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Hot Tub<br>-NO Pets (fines remitted) <br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0404030860

Exquisite in East Orleans, Heated Pool, Fire pit, Gym! Linens Included, Beds Made Pets Considered Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to The Breakaway, a stunning vacation home nestled in the picturesque Tonset Area of Orleans, Massachusetts. This luxurious property offers a perfect blend of comfort and elegance, making it an ideal retreat for families or groups seeking a memorable getaway. With 5 spacious bedrooms and 5.5 bathrooms, this home comfortably accommodates up to 14 guests, ensuring everyone has their own space to relax and unwind. As you step inside, you’ll be greeted by a beautifully designed interior featuring a gas fireplace that adds warmth and charm to the living area. The central air conditioning throughout the home ensures a cool and comfortable atmosphere, even on the warmest summer days. The fully equipped kitchen is a chef’s dream, complete with modern appliances, ample counter space, and a dining area perfect for family meals. The outdoor space is truly a highlight, boasting a heated private pool and a hot tub, perfect for soaking up the sun or enjoying a relaxing evening under the stars. The fenced yard provides a safe space for children and pets to play, while the outdoor seating areas and fire pit create an inviting atmosphere for gatherings. For those looking to stay active, the property features a gym and a game room equipped with a pool table and entertainment options, ensuring fun for all ages. Each bedroom is thoughtfully appointed, with the master suites offering TVs and sound systems for added convenience. Located just a short walk from the beach and near various attractions, including local Breweries and outdoor adventures, The Breakaway is the perfect base for exploring all that Cape Cod has to offer. Don’t miss out on this exceptional property—book your stay today and create unforgettable memories! Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14511 - Sunny Shores: Sunroom, Mins to Beaches, Central AC! A vacation to Eastham means stunning shorelines, delicious restaurants, and peace and quiet that comes with a small Cape town. You’ll be living your best beach life while soaking in the summer sun at Sunny Shores! <br><br>Pushing open the light blue-gray front door, you’ll step into a spacious living room, with a large sectional in front of the wall mounted TV. Just passed the sectional, there is a game table perfect for family game nights with views of the spacious backyard through the large window. <br><br>A large kitchen can be found on the first floor, with easy access to a smaller dining area, perfect for morning coffee and breakfast with views of the salt marsh, and a larger dining table under the stylish chandelier, with natural light pouring in from the patio doors and windows. <br><br>The beautiful sunroom is found at the rear of the home, surrounded on three sides by windows, letting the salty air in while keeping any unwanted bugs out. Outside, a patio with outdoor dining is a great space to enjoy meals under the stars.<br><br>Other amenities include a washer and dryer, a propane grill and central A/C. Pristine beaches mere minutes from your front door, and views of the blue herons flying over the First Encounter Salt Marsh await you on your next vacation at Sunny Shores!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $35/night per dog)<br>-Sleeps 8<br>-2 Floors (1st Floor + 2nd Floor)<br>-1,808 Sq Ft<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 2 Twin Beds<br>-1st Floor Bedroom: 1 King Bed<br>-2nd Floor Bedroom: 1 King Bed w/ Jack and Jill en suite Full Bathroom<br>-2nd Floor Bedroom: 2 Twin Beds w/ Jack and Jill en suite Full Bathroom<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom: w/ Shower<br>-2nd Floor: Full Bathroom w/ Shower (Jack and Jill Style en suite King Bedroom and 2 Twins Bedroom)<br>Other Amenities<br>-Fully Equipped Kitchen with Dishwasher<br>-Central A/C via mini splits<br>-Fireplace is NOT for guest use<br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV with Streaming<br>-Washer & Dryer (1st Floor)<br>-Patio with Outdoor Dining<br>-Sunroom<br>-Propane Grill<br>-Outdoor Shower<br>-Fire Pit<br>-Ping Pong Table<br>-Private Yard<br>-0.6 Miles to First Encounter Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0406610860

14437 - Over the Bridge: Lovely Home Close to Bike Path and Beach! This lovely vacation home, located on the bayside of Eastham, offers the ideal combination of comfort and convenience, and is the perfect place to spend your summer vacation with the family. Hop on your bicycle and in three minutes you will be at the Cape Cod Rail Trail, where you can enjoy a the remarkably picturesque scenery and experience many of the wooded forests, lakes and quiet kettle ponds, salt marshes, bogs, winding creeks, and sandy beaches that the Lower Cape has to offer. First Encounter beach is a just a few minutes drive from the home, as well as Herring Pond and Boat Meadow. Our property provides the level privacy that you and your family would like, while being conveniently close to all the attractions that you want to see. Walk through the door and enter our wonderful three-season sunroom, which connects to the newly-updated deck and outdoor shower. You will love the backyard setting, behind mature trees offering a private yard with a fire pit. Inside, you will find an updated kitchen, spacious dining area, and living room with a gas fireplace, flat screen TV, and comfortable couch seating. The basement features a ping pong table, mini air hockey, and lounge area with TV entertainment. There are three bedrooms, sleeping a total of ten guests, as well as two full bathrooms. Other amenities include smart TV, WiFi, A/C, a washer/dryer, and sheets and towels provided at no extra cost. Our home is also dog friendly, so don’t forget to bring your furry friend along too! <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 9<br>-3 Floors<br>-1st Floor Master Bedroom: 1 Queen Bed<br>-2nd Floor Bedroom #1: 1 King Bed + Twin Trundle<br>-2nd Floor Bedroom #2: 1 Full Bed + 2 Twin Beds<br>-Window A/C Units/Floor A/C Unit<br>-2nd Floor Mini-Split A/C Unit<br>-Smart TV/<br>-Washer/Dryer in Basement<br>-Ping Pong Table & Mini Air Hockey<br>-Gas Fireplace<br>-Outdoor Shower<br>-Private Yard<br>-Next to Rail Trail<br>-Minutes to First Encounter Beach & Herring Pond<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0413450860

Just 5 minutes from Cape Cod’s stunning beaches like Rock Harbor and near Orleans’ many shops & restaurants. This spacious home has a bright sunroom, AC, deck + grill, garage to park in, beach chairs & toys, dedicated workspace, and a fully equipped kitchen. Games & puzzles available for rainy days. Bike along the Cape Cod Rail Trail, with an entrance near our home, or go Hiking at a nearby trail. Ideal for families or groups, this home offers the perfect balance of relaxation and adventure. HIGHLIGHTS: ★ 4 Bedrooms + 6 Beds ★ Less than 2.5 miles to Rock Harbor Beach ★ 2.5 Bathrooms ★ Beautiful enclosed sunroom ★ Large Deck with a table and seating ★ Beach toys and chairs provided ★ 5 min to charming downtown Orleans, 8 min to downtown Eastham ★ Close to First Encounter Beach, Coast Guard Beach, Herring River, Nauset Light Beach & more ★ Office with a monitor attached to bedroom #1, plus desks in Bedrooms 2 & 3 ★ Outdoor shower for cleaning up after the beach ★ Sonos sound system ★ Dining table ★ Numerous hiking trails near the home ★ Entry to the Cape Cod Rail Trail for biking, running or walking near the house ★ Fully equipped kitchen with all the appliances & utensils you would need ★ Smart TV in the living room + master bedroom ★ Piano keyboard in the cozy living room ★ Grill + utensils (must provide propane) ★ Games and puzzles provided for family fun ★ Washer/Dryer ★ High-speed WiFi ★ AC (central air) ★ Keypad entry (no keys to worry about) ★ Drip coffee machine + grounds provided ★ Very family-friendly location - surrounded by wonderful neighbors ★ About 30 minutes to the Cape Cod Gateway airport in Hyannis BEACH DETAILS: The house is closest (2.5 miles) to Rock Harbor Beach. We’re also close to several other options on the bay side (First Encounter Beach, Skaket Beach, Cole Beach) and on the more spacious ocean side (Coast Guard Beach, Nauset Light Beach, Nauset Beach, Marconi Beach)! BEDS: Bedroom 1: King Bed + Smart TV + Dedicated Workspace (on first floor) Bedroom 2: Queen Bed + desk Bedroom 3: Queen Bed + Futon + desk Bedroom 4: Twin Bunk Beds BATHROOMS: Bathroom 1: Full size bathroom on the first floor Bathroom 2: Full size bathroom on the second floor Bathroom 2.5: Half bath near the main living area on the first floor NEARBY PLACES (alphabetical): ★ 400 East Restaurant ★ Beacon Room ★ Brewster Fish House ★ Cape Cod National Golf Club ★ Cape Cod Rail Trail ★ Captains Golf Course ★ Casa del Cabo ★ Cibo Italian Kitchen & Market ★ Chatham Yacht Club ★ CVS ★ Downtown Eastham ★ Downtown Orleans ★ Heart of the Sea ★ The Knack ★ Liquor ’n More ★ Mac’s Market & Kitchen ★ Nauset Beach ★ Nickerson State Park ★ Orleans Cove ★ Pleasant Bay ★ Starbucks ★ Stop & Shop Grocery ★ Twenty-Eight Atlantic Restaurant ★ Wequassett Resort NEARBY TRANSPORTATION: 30-40 minutes from the following places: ★ Cape Cod Gateway Airport ★ Provincetown Ferry ★ Hy-Line Cruises (ferries to Martha’s Vineyard and Nantucket) ★ The Steamship Authority (ferries to Martha’s Vineyard and Nantucket) Located on a quiet street in charming Eastham, our location offers the perfect blend of privacy and convenience. Nestled just minutes from world-famous Cape Cod beaches and the vibrant shops, cafes, and galleries of downtown Orleans, the neighborhood is ideal for exploring the best of Cape Cod. Enjoy nearby bike trails, fresh seafood spots, and nature preserves, all while savoring the peaceful, laid-back coastal atmosphere Eastham is known for. Enjoy nearby beaches, lakes, and trails! Ocean side beaches: ★ Coast Guard Beach ★ Nauset Light Beach ★ Nauset Beach ★ Marconi Beach Bay side beaches: ★ Rock Harbor Beach ★ First Encounter Beach ★ Skaket Beach ★ Cole Beach Lakes: ★ Wiley Park in Eastham - includes a playground, Great Pond Beach, and walking trails ★ Long Pond Beach - beach & beautiful sunsets, close to the Cape Cod Rail Trail Walking / Hiking: ★ Cape Cod Rail Trail ★ Upper Boat Meadow Trail ★ Fort Hill Area ★ Mass Audubon Wellfleet Bay Wildlife Sanctuary ★ Wiley Park Ample room for parking in the driveway for vehicles. 1 Car can also park in our garage. While we are not far from many great attractions, having a car is recommended for this location. Please note we do not supply propane for the grill, but there may be some leftover from a previous guest.

14447 - The Dive In: Beautiful Spacious Family Retreat w/ Pool! Look no further than this beautiful spot for your next Cape Cod getaway, the house is spacious, clean and has everything you need to enjoy a great vacation! The star feature is its huge fenced-in yard with gorgeous private pool, tall pine trees, and large deck for enjoying grilling out while the kids run around and play. You’ll also enjoy two separate living/relaxing spaces that each have their own TV, so two separate groups can enjoy watching whatever they like. The kitchen is modern and well equipped, which will make whipping up meals for a crowd a cinch. Your days can be spent relaxing at the beach, taking a Seal Tour in Chatham, Whale Watch in Provincetown, wine tasting at Truro Vineyards, and more —the mid and Outer Cape have so much to offer! Return home after a day of fun to take an outdoor shower, jump in the pool and unwind with friends and family under the stars from the comfort of your own backyard. Other amenities include WiFi, cable TV, gas grill, central A/C, and washer/dryer. Fresh sheets and bath towels are provided free of charge. <br> <br> Home Details:<br> -Sleeps 8<br><br>-2 Floors<br><br>-2nd Floor Bedroom #1: 1 King Bed<br><br>-2nd Floor Bedroom #2: 1 Full Bed<br><br>-2nd Floor Bedroom #3: 1 Full Bed<br><br>-2nd Floor Bedroom #4: 1 King Bed, 1 Twin Bed w/ Trundle<br><br>-2nd Floor Common Area: 2 Twin Beds<br><br>-Central AC <br><br>-Cable TV<br><br>-WiFi<br><br>-Washer/Dryer <br><br>-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br><br>-Outdoor Shower<br><br>-Gas Grill<br><br>-NO DOGS! (heavy fines remitted)<br><br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br><br>-Cleaned with Hospital Grade Disinfectant<br>C0405890860

This property is Professionally Managed by Pretty Picky Properties Luxurious Orleans Estate with Pool, Cabana, Game Room, and Stunning Finishes Sleeps 14 6 Bedrooms, 6.5 Baths Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pets Considered Pool is open from Memorial Day to Columbus Day Welcome to your dream vacation home in Orleans! This custom-built, newly constructed property offers the perfect blend of luxury and comfort, designed to make your Cape Cod getaway unforgettable. Main House Highlights 5 Spacious Bedrooms: Each bedroom features a private en-suite bathroom, ensuring comfort and privacy for all guests. There’s one king bedroom on the main level, the primary bedroom suite is upstairs with a king size bed, the other two rooms have a king and queen respectively. The lower-level bedroom is the kid lair with 2 sets of queen over queen bunks. Vaulted Ceilings: The open concept living, dining, and kitchen areas are bathed in natural light and exude sophistication with soaring ceilings and high-end finishes. Gourmet Kitchen: Fully equipped with top-of-the-line appliances, perfect for preparing meals and entertaining. Luxurious and custom décor throughout: no expense was spared in outfitting the home with décor and furniture rarely seen in a vacation rental property. Outdoor Oasis Heated Saltwater Gunite Pool: Take a refreshing dip or lounge poolside in style. Hot Tub: room for 6 to enjoy! Pool House with Cabana Bar: Enjoy cocktails by the pool with a full cabana bar, a bathroom, and an additional bedroom for added convenience and flexibility. Entertainment Galore Game Room: The massive game room is a paradise for kids and adults alike, featuring Pop-A-Shot basketball, ping pong, air hockey, and more. High-End Furnishings: Every room is thoughtfully decorated with custom, high-quality furnishings to elevate your stay. 5-minute drive to Orleans Center and Nauset Beach: shopping and dining or head to one of the best beaches on the Cape. Whether you’re lounging by the pool, hosting a family game night, or enjoying the luxurious finishes of this one-of-a-kind property, this Orleans retreat is the perfect base for your Cape Cod vacation. Book now and experience the pinnacle of coastal living! Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14458 - Cerulean Skies: Walk to Water Gorgeous Outdoor Space! This newly renovated summer cottage is the ideal spot for an unforgettable Cape Cod Vacation! Walk into the open concept living room with vaulted ceilings and relax on the couches under plenty of natural light. To your left, you’ll find stairs that lead up to the 2nd floor TV/Lounge room. Open to the living room is a full-equipped, eat-in chef’s kitchen with oversized black granite countertops, new stainless steel appliances, and an abundance of kitchen supplies--all impeccably organized and well maintained! To the right of the kitchen is a large formal dining table for family meals, or you can choose to walk a few steps further and enjoy a meal at the picnic table in the screened-in sunroom. <br> <br> Also on the first floor are two bedrooms, each with two twin beds, and matching rustic white shiplap accent walls. At the end of the hall on your left, you’ll find the first of two sparkling clean bathrooms, with a luxurious white tile shower and spacious granite vanity. Straight ahead in the closet, you’ll find an Electrolux stackable Washer & Dryer, and to your right enter the Master bedroom with a Queen bed, ceiling fan, his/her matching closets, private en suite bathroom, and a slider that opens up to the deck and patio area. <br><br>Enjoy the private neighborhood beach just a short walk down a dirt road, or you can get in your car and take a quick drive to Thumpertown or Kingsbury beach. Other amenities include WiFi, Smart TV with cable, gas grill, dog-friendly, and sheets and bath towels provided for each guest. Lastly, you’ll also be conveniently located close to Eastham favorites like Arnold’s Lobster & Clam Bar, Hole in One Donuts, Fairway Family Restaurant, and the Bike Trail! <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 6<br>-2 Floors<br>-1st Floor Master Bedroom: 1 Queen Bed<br>-1st Floor Bedroom #2: 2 Twin Beds<br>-1st Floor Bedroom #3: 2 Twin Beds<br>-2nd Floor Lofted Family Room<br>-Central A/C<br>-Cable TV<br>-Smart TV <br>-WiFi<br>-Washer/Dryer <br>-Gas Grill <br>-Fire Pit<br>-Deck with Furniture<br>-Outdoor Shower<br>-Walk to Water<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0411970860

Stunning cape contemporary style waterfront home with walls of glass and panoramic salt water views from most every room. This home was completely renovated with designer high-end kitchen, gleaming hardwood floors, custom fireplace, and every modern amenity. 1st floor Primary bedroom with king bed, dressing area and en-suite bathroom. Lower level offers a den with sofa bed and 3 more bedrooms. 2 with Queens and 1 with 2 twins. Magnificent landscaping with specimen trees, plants and rock walls. Your own private steps to the sandy shoreline of Town Cove’s water. Perfect for paddle boarding, and kayaking. Air conditioning throughout. Outdoor shower to rinse off after the beach. Gas outdoor fire pit with seating area on lower patio to finish off the evening. **Blankets and Pillows are provided, but you will need to bring or rent sheets and towels**

14424 - Bayberry Bliss: Gorgeous Architectural Home w/ Water Views! This gorgeous, architectural digest brand-new water-view home could be all yours for an incredible vacation! Enjoy the chef’s kitchen, 180-views of Cape Cod Bay, and easy walk to a private neighborhood beach (no crowds)! In addition to the large, pristinely equipped eat-in kitchen, there are 4 bedrooms, and luxurious living spaces overlooking to the south First Encounter Beach! With construction finished in 2017, this house is truly brand-new, and offers plenty of high-end spaces for the whole party to enjoy. <br><br>The first floor master bedroom offers a king bed and large sliding doors for easy deck access, as well as a beautifully modern en suite bathroom. Two more bedrooms are also on the first floor separated by a large foyer, one with a queen sized bed, and one with two twin beds, both with easy access to another gorgeous bathroom. Downstairs offers a fourth bedroom, and unlike many “basements”, this room offers outdoor access and plenty of light, as well as a queen bed. <br><br>The 2nd floor of this home provides exceptional living, dining, and kitchen space in an open concept that allows for great views of the ocean. The kitchen is equipped with high-end appliances and offers seating both inside and outside on a beautiful 2nd floor deck area. A third bathroom is found across from the kitchen pantry closet, as well as a small wine bar equipped with a wine fridge! <br><br>If you enjoy the new amenities and luxuries but still want to enjoy old Cape Cod, this home is sure to please even the pickiest of party members. <br> <br>Home Details:<br>-No Pets(Fines Remitted)<br>-Sleeps 8<br>-3 Floors<br>Bedrooms<br>-Total 4<br>-1st Floor Master Bedroom: 1 King Bed w/ en suite Full Bathroom<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Twin Beds<br>-Ground Floor Bedroom: 1 Queen Bed<br>Bathrooms<br>-Total 3.5<br>-Ground Floor: Full Bathroom w/ Shower<br>-1st Floor: Full Bathroom w/ Shower (en suite King Bedroom)<br>-1st Floor: Full Bathroom w/ Shower/Tub combo<br>-2nd Floor: Half Bathroom<br>Other Amenities<br>-Central A/C<br>-Smart TV with cable<br>-Wifi<br>-Washer and Dryer located in basement<br>-Tub<br>-Outdoor Shower<br>-Private Yard<br>-Gas Grill<br>-Water views and less than 100 yards from private neighborhood beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0404170860

14465 - The Beach Flower: Beach House Short Walk to Kingsbury Beach! As soon as you arrive at Beach Flower, you are welcomed in by the farmer porch with seating for four to relax with your favorite chilled beverage and watch the world go by. Enter the three-bedroom home and you will find a spacious living area with plenty of room for the family to enjoy a night of board games or movie streaming on the smart TV. <br> <br><br>Adjacent to the front living room, you’ll find the dining area with a banquet table that seats six as well as the kitchen, which is fully equipped with all the wares needed to prepare breakfast, lunch or dinner. Guests can access the private backyard through the back door located in the kitchen. The large, level backyard, which is perfect for lawn games (bring your favorites), features a patio area with a picnic table and a charcoal grill (don’t forget to bring your own charcoal), plus an enclosed outdoor shower and a fire pit for chilly nights. <br><br>The single-floor home has three bedrooms: the primary bedroom has a queen bed and en suite bath with a shower; a second bedroom facing the front of the home features a king bed; and the last bedroom has two twin beds.<br>Leave your car in the driveway and walk to Kingsbury Beach, only seven minutes down the street. The beautiful bayside beach is great for walking and catching nightly sunsets. Other nearby attractions include well-known and well-liked breakfast spot, The Hole in One, and the Red Barn, a casual pizza spot. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 6<br>-1 Floor<br>-3 Bedrooms / 2 Bathrooms<br>-Master Bedroom: 1 Queen Bed w/ en suite Full Bathroom<br>-Bedroom #2: 1 King Bed<br>-Bedroom #3: 2 Twin Beds<br>-Master Bathroom: Full Bath w/ Shower<br>-Bathroom #2: Full Bath w/ Tub/Shower Combo<br>-Central Heat & A/C <br>-Smart TV w/ Streaming & Cable<br>-WiFi<br>-Washer/Dryer (basement access via bulkhead)<br>-Enclosed Outdoor Shower<br>-Private Yard<br>-Charcoal Grill <br>-Lawn Chairs w/ Fire Pit<br>-Porch w/ Furniture<br>-Deck w/ Chairs & Dining Table<br>-1 Mile to Bike Trail<br>-Walk 1/4 Mile to Kingsbury Beach<br>-Walk 1/3 Mile to Wiley Park on Great Pond<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0056230860

This property is professionally managed by Pretty Picky Properties. East Orleans Vacation Estate Includes Guest House, Heated Pool, hot tub Sleeps 12 6 Bedrooms, 6.5 Baths Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pets Considered - 25lb. limit Pool is open from Memorial Day to Columbus Day Privately ensconced on 1.25 acres in its charming East Orleans neighborhood, this exceptional property beckons your group of up to 12 for a Cape Cod vacation that will long be remembered fondly. The property is comprised of the main house plus a separate guest house, both the beneficiaries of the meticulous owners. Living Spaces: Naturally, the majority of the 4,190 sq. ft. of interior living space is found in the handsome main house. As you enter the welcoming foyer and proceed straight ahead, you’ll find yourself in the appealing dining area accommodating 12 around the table, with sliders out to the deck beyond. To your left, you’ll discover the gleaming and fully equipped chef’s kitchen with all high-end appliances, including a gas range and two dishwashers. The countertops are granite as is the generous center island with a prep sink and seating for 5. On the other side of the dining area, the beautiful and comfortable living room awaits, with its masterful furnishings and marble clad gas fireplace. There’s also a convenient half bath just off the kitchen. The home’s lower level provides a lounge with a complete wet bar, TV, and wine fridge. This space walks out to a good-sized patio with a firepit overlooking the pool. Kids of all ages will love the game room. Air Hockey, anyone? How about some arcade games? Out in the guest house, you’ll be impressed by the sense of space and light due to the two-story vaulted ceilings in the main living space. There’s also a full kitchen here with a center island with stool seating for three. There’s a handsome spiral staircase here that leads up to one of the guest house bedrooms. Sleeping Arrangements: This stunning home sleeps 12 in six bedrooms, each with its own private full bath ensuite. The main house has one of the property’s primary bedrooms on the main level. It has a big king-size bed, a good-sized TV and a walk-in closet. On the second level you’ll find another king primary bedroom and a second king bedroom that’s only slightly smaller. The lower level provides another bedroom and a private full bath. This one is a twin bed plus a pull-out second twin under. The property’s final two bedrooms are in the guest house. The main level bedroom has yet another king bed, also with a private bath; the second bedroom up the spiral staircase has a queen plus private bath. Outdoor Spaces: This vacation estate was created with outdoor summer living in mind. You can lounge on the large deck with an elevated view of the heated saltwater pool. The patio below may be where you decide to serve dinner most evenings. Why not? You have an umbrella shaded, ample dining table and chairs, and a big gas grill to fire up at any time. Walk down the steps from the deck to the stone patio and you’ll find the gas fueled fire pit and the enclosed outdoor shower. Maybe a quick dip in the pool and a few minutes in the soothing hot tub before dinner? This is truly Cape Cod outdoor summer living at its finest. Location: Not that you’ll feel the need to venture far from this resort-like property, it’s good to know your feet can be in the sweeping sands of world famous Nauset Beach in just an eight-minute drive. It’s just three minutes to East Orleans Village and Nauset Farms Market, known for their custom butcher shop, fresh local produce, generous deli sandwiches and mouthwatering homemade desserts. Or drive into Orleans Village Center to sample the unique shops, galleries and restaurants there, such as the addictive Hot Chocolate Sparrow. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties. Private Orleans resort-style compound with heated pool & spa, fire pit and cabana Rents from Friday to Friday during summer weeks Linens included Pool & Hot Tub open from Memorial Day to Columbus Day Your multi-generational or multi-family summer vacation has found its home. Experience this stunning property with plenty of amenities for the entire family. The home features five bedrooms and sleeps up to 14 guests. The owners have added a heated salt water pool (18’x40’), hot tub and gas fire pit. There is also a cabana off the pool that features a sauna, full bar, half bath and comfy seating area with a big screen TV. In addition, there is a basketball hoop located off the back of the home. When you choose to venture out from your own private resort, world-famous Nauset Beach is less than a mile and a half down the road. Several restaurants, shops and an ice cream parlor are just a short walk away. Inside, on the main level, the open floor plan creates a wonderful space for the whole family to gather. You will find a chef inspired kitchen with high-end, stainless steel appliances including a gas range. The kitchen opens to a living area with large screen TV adjacent to a beautiful dining area. The main level provides two primary suites. Each is outfitted with a king size bed and en suite full bath. One of the primary suites has an enclosed deck with a commanding view of the magnificent patio and pool area. On the upper level, you’ll find three more bedrooms, each with a private bath. The first bedroom on the second floor features a queen size bed plus a day bed. Across the hall is another bedroom also with a queen size bed, a day bed plus en suite bath. The final bedroom upstairs is the perfect bunk room for the kids which is accessed from a separate stairway. It features two bunk beds (full size bed on the lower bunks) plus two twin beds, full bath and a private TV/game room. It’s a wonderful “clubhouse” where kids have their own space to play video games or watch their videos. This home is equipped with all the modern amenities you’d expect: high end furnishings, top quality bedding, central air conditioning, Wi-Fi, and cable TV. This property provides the accommodations you need for your group of up to 14 to enjoy your own private mini-resort. Whether it’s spending the day at the pool, relaxing in the sauna, or shooting hoops, the entire family can find something to enjoy. Once the day is done, marvel at the beautiful starry nights while dining al fresco on the deck. Or enjoy a beverage in the hot tub while discussing the plans for the next magical day on Cape Cod. Please note: pool and hot tub are open Memorial Day - Columbus Day. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14504 - Coastal Grove: Spacious Mins from Beach & Dogs Welcome! Any time you visit Eastham on the Cape, you are sure to fall in love with the gorgeous beaches and quiet neighborhoods throughout this cozy town. Add on some delicious restaurants and a stunning home to call your own all vacation long, and you won’t be able to resist falling in love with this Coastal Grove! Walk up the step stone path and enter into this lovely wooded oasis. Entering into the home, you’ll find yourself in the home’s open concept living room, dining room and kitchen, where you can cook up a meal and chow down before watching your favorite movie under the beautiful vaulted ceilings. Just off the living room, a beautiful sunroom with exposed wood beams and small breakfast table is a great space to enjoy a morning coffee or nighttime cocktail. When it’s time to get some sun, head to the back deck, where an outdoor dining table awaits dining alfresco. The large yard allows plenty of room for your four-legged friends to run around. The first floor houses three bedrooms. The home’s primary bedroom features a queen bed, private back deck and ensuite full bathroom. The second bedroom offers a full bed, while the third has two twin beds. An open loft area upstairs includes additional beds. Other amenities include a washer and dryer, mini-split a/c units, and an outdoor shower. Nothing says coastal living more than enjoying a Cape Cod vacation in Eastham, at the Coastal Grove! Home Details: -Dogs Welcomed (w/fee of $40/night per dog) -Sleeps 6 -2 Floors (1st Floor + 2nd Floor) -1,914 Sq Ft Bedrooms -Total 3 -1st Floor: 1 Queen Bed w/ ensuite Full Bathroom -1st Floor: 1 Full Bed -1st Floor: 2 Twin Beds Bathrooms -Total 2 -1st Floor: Full Bathroom with Shower (ensuite Queen Bedroom) -1st Floor: Full Bathroom with Tub/Shower Combo Other Amenities -Fully Equipped Kitchen with Dishwasher -Mini-Split A/C Units -Smart Lock/Self Check-In -WiFi -Smart TV with Streaming -Washer & Dryer (1st Floor) -Deck with Outdoor Dining and Built-In Seating -Screened-In Porch/ Sunroom -Propane Grill -Outdoor Chimnea -Outdoor Shower -Private Yard -Sheets and Bath Towels Provided with Beds Made Upon Arrival -Cleaned with Hospital Grade Disinfectant C0413472240

This property is professionally managed by Pretty Picky Properties Luxurious 5- Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water! 5 bedrooms sleeps 12 Linens included, beds made Rents Friday to Friday in Peak Season Pets Considered (Small dog) Please note: pool and hot tub are open Memorial Day - Columbus Day. Escape to the heart of Lower Cape Cod in this newly renovated, luxury vacation home in East Orleans! Perfect for families and groups, this spacious 5-bedroom retreat offers the perfect blend of modern comfort and classic coastal charm. Inside, you’ll find a fully equipped, modern kitchen with everything you need to prepare gourmet meals, plus a large dining room with seating for 10 -- perfect for gathering after a day at the beach. The main level features two elegant bedrooms, both with a queens, each with new, spa-like private baths. Upstairs, two additional bedrooms. One has a spacious King and the other with a queen plus a twin with a trundle. There is a luxurious full bath upstairs as well. New for 2026: 5th bedroom as primary bedroom and private en-suite. Step outside and experience your private Cape Cod oasis -- a heated saltwater pool, relaxing hot tub, gas fire pit and a fully equipped outdoor kitchen make entertaining a breeze. Lounge in the poolside cabana, fire up the grill, or unwind under the stars after a day of exploring. Nature lovers will love the short walk to a nearby saltwater river, perfect for kayaking and paddleboarding. Plus, you’re just under a mile to Orleans Center for shopping and dining, and a 5-minute drive to both Nauset Beach and Skaket Beach—giving you the best of both the Atlantic Ocean and Cape Cod Bay. This stunning getaway has everything you need for an unforgettable Cape Cod vacation. Please enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation, Get Picky! ®

This home is professionally managed by Pretty Picky Properties Grand Villa Overlooks Nauset Beach & the Atlantic, Heated Pool, Hot Tub & Gas Fire-pit! Rents Friday to Friday Off-season partial weeks available. Sleeps 14 Linens Included/Beds Made Pool and hot tub are open Memorial Day - Columbus Day Your group of up to 14 will vacation in style at this superb ocean side manor house at famous Nauset Beach in East Orleans. The stunning location provides panoramic views of the beach and ocean from both levels of the house. And you have a very short walk to the beach. The property also features a 36’x18’ heated pool, hot tub and gas fire pit!! The spacious, social, fully loaded kitchen anchors the main level and includes a breakfast bar with high boy seating for four. A few steps away, the large dining room easily seats 10 and can accommodate more. Relax in the exquisite living room with lounge seating and a large flat screen TV. This home has Sonos sound system off the back deck and in the lower level living space. It is centrally air conditioned and has hi-speed Wi-Fi and cable TV. A large, covered patio is just off the living room, with a dining table and chairs, plenty of lounge seating and views of the Atlantic. A separate lounge/bar room offers a wet bar with fridge, another TV, and bar seating for three. Walk out from there to a beautiful, hexagonal screened porch which leads to the pool deck. There is one bedroom on the main level, a roomy primary suite with a King size bed and full bath en suite with a walk in shower. The main level also includes a half bath and quiet den/study to serve as your work station, if necessary. On the upper level, you’ll first encounter another lounge area, which walks out to the upper deck that presents 180-degree breathtaking views of Nauset Beach and ocean. Comfy lounge seating here too, including a king-size super comfy sleeper sofa. On this level, you’ll find four more bedrooms. There’s a second, oversized primary suite, with a king size bed plus twin day bed with a twin trundle below. There is a full bath en suite, of course. Another bedroom suite features a King size bed and private full bath. Bedrooms #4 and #5 can be closed off to create a two-bedroom suite. Both bedrooms feature a queen size bed with a standard twin bed and twin trundle bed. The two bedrooms share a full bath between, Jack & Jill style. The lower level of the home houses an extraordinary full home theater with a projector, 10-foot screen and luxurious lounge seats with cup holders for up to 12, plus giant bean bag seating for more. What an amazing place should the weather not cooperate or for your evening entertainment. Also on this level: a workout room, a ping pong table, and a half bath. There are four full and two half baths in all. The yard and grounds provide plenty of space for kids to play safely. There is also a gas grill and horseshoe pits to keep everyone entertained. Consider planning your summer vacation at this truly remarkable property in one of Cape Cod’s most coveted locations. Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties Brand New Luxury Home with Heated Pool, Walk to Rock Harbor Sleeps 10 Linens Included, Beds Made Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Ideally situated on the bay side of Orleans, this brand-new property features a 35’ x 18’ salt water heated pool, with a built-in spa and auto close cover. It is complemented by a large hardscape patio with plenty of lounge space. You can walk a mere 0.4 miles to scenic Rock Harbor for boat charters, seafood and the best sunsets on Cape Cod! There’s also a beach for swimming! Back at the house your group of up to 10 will be delighted with luxury living tastefully furnished throughout. Start with the custom chef’s kitchen, fully outfitted with top-line everything – from the high-end appliances to the 10-foot-long granite topped island with bar seating. The adjacent café dining table offers comfortable casual seating which walks out to the patio and pool. There is more formal dining for eight in the separate dining room as well. The kitchen flows into the adjoining sunroom which is bathed in cheery sunlight, thanks to the large windows, and vaulted, handsome bead-boarded ceiling with skylight. This level is also home to the primary bedroom suite with its generous king size bed and large private, radiant heat bath with a twin sink vanity and oversized step-in glass shower. Also located on the main level: a half bath, the laundry/pantry and mudroom. Upstairs are three generously sized en suite bedrooms: One has a king bed, the next has a queen bed. The final bedroom has a queen plus 2 twin beds. Comfy sleeping for up to 10. This luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning. Please enter in your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Please note: pool and hot tub are open Memorial Day - Columbus Day. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties. Upscale Vacation Estate with Heated Pool Near Nauset Beach Sleeps 12 Rents Friday to Friday in peak summer Linens Included, Beds Made Pool & Hot Tub open from Memorial Day to Columbus Day Completely renovated in 2024, here is the elite Cape Cod vacation experience your group of up to 12 is looking for. Start with location. World famous Nauset Beach is a mere 1.5 miles down the road. You can easily walk to the popular Barley Neck Inn and East Orleans Village with its inviting shops, ice cream and much more. Nauset Farms Market provides a professional butcher ready to assist you in choosing the ideal entree for that night’s grilling delight, as well as farm fresh produce, freshly made deli sandwiches and taste tempting homemade desserts. The property itself is a multi-structure compound, consisting of the main house, guest cottage, pool cabana, office/recreation center, and believe it or not, its own freestanding snack shack. Outdoor Living Space As you would expect, your outdoor living experience centers on the large, heated, saltwater pool and hot tub. You’ll find plenty of comfy lounge chairs for your poolside pleasure. The beautiful landscaping is a true delight. Be sure to experience the enclosed outdoor shower, a Cape Cod ritual that never gets old. Take a break from the sun in the poolside cabana. You’ll find a beverage center, half bath and laundry area inside. Put the gas grill to work and plan to dine on the large pool patio. You will also find a large firepit on the patio off the back of the main house. Indoor Living Space The fully equipped chef’s kitchen is a pleasure. New stainless-steel appliances and beautiful granite counters make meal prep a rewarding experience. The kitchen flows into the large dining area and family room with a gas fireplace. At the front of the house on the main level you’ll discover one of several recreation areas at this property, featuring a pool table. The guest house has a kitchen, living room and full bath. Still another structure at this property is the game room/office. It provides a work station, half bath and bar/lounge with a large TV. And then, just for fun, there’s the snack shack, which features a hot dog roaster, deep freezer for ice cream, refrigerator, and a sliding window for service. Sleeping Accommodations The main house has four bedrooms, each with a full bath ensuite. The upper level provides the king primary suite, and its beautiful private full bath is immense. It also has a gas fireplace and balcony overlooking the compound. There are two more bedroom suites upstairs via a separate stairway, one with a king size bed and the other with a queen. The lower level of the main house is home to three queen-sized beds and en suite bath. The guest house features a bedroom with a queen size bed and full private bath. In all the property has five full and three half baths. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties. "Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove Sleeps up to 24 in three dwellings Linens and bed making included Pets Considered up to 25 lbs. Weddings not permitted on property Pool is open Memorial Day - Columbus Day This Orleans Estate is located in the heart of Orleans Village on picturesque Town Cove. Bring the whole family and leave the cars in the driveway for the week. You’ll spend countless hours around the pool and spa at the Main House. There’s plenty of room for everyone to gather around the fire pit and cook out poolside at the outdoor kitchen. You can walk to everything in Orleans Center, including some of the best restaurants in town, village shops and of course, ice cream. There are four ice cream shops within walking distance! The mid-century homes have been recently updated with all the modern conveniences while retaining much of the original charm. The large 1.3 acre lot is waterfront on Town Cove and has a heated pool and spa (open Memorial Day - Columbus Day). The large lot provides plenty of recreation space on the gently sloping lawn. Hold your own version of the Whiffle Ball World Series. Town Cove is a great place to drop an owner-provided kayak or SUP and explore the in-land waterways of Nauset Cove and Nauset Marsh. Bring your boat and use the adjacent town boat ramp to motor your way to Nauset Beach by boat! The Main House underwent a full remodel in 2023, you have an updated kitchen with granite counters and new appliances, including a huge side-by-side refrigerator and two dishwashers. There are two dining areas along the back of the house so that large groups can dine together. There is also an enclosed porch overlooking the lawn, pool and cove beyond. The house is great for bringing family together but you have enough space to spread out as well. There are 3 large seating areas in the Main and Carriage Houses that are great spots to watch a ball game or for the kids to watch their shows/movies. The Main House has 5 bedrooms, 5 full baths and 1 half bath. You’ll find one of three primary suites on the main level of the Main House with a king size bed, sitting area and beautiful ensuite bath. There is also a powder room on the main level and living room with separate card-table room. Upstairs in the Main House, there are 3 bedrooms: the second primary suite with a king bed and a private full bath, the third primary suite features a king size bed and ensuite bath, and the third bedroom has a queen size bed with a twin bunk above. There is a full bath for guests of this room in the hallway with a tub/shower combination. In the lower level, you’ll find an extra sleeping area with 2 twin beds for overflow sleeping. Plus a wonderful new media room, laundry room and there is a full bath down here as well plus an outdoor shower not far away. Next door in the Carriage House, you’ll find a second full kitchen, a dining area, a powder room, a primary suite with king size bed and a private full bath on the main level. Upstairs in the Carriage House, you’ll encounter a loft space with a TV and cozy couch. There is a full bath and a bedroom with a queen sized bed plus 2 twins. The third structure, the Guest House has been fully remodeled – brand new kitchen with stainless steel appliances and granite counters. On the main level is a queen bedroom with full bath while upstairs you have a kid’s room with a bunk bed (full under a twin) and another twin with trundle bed with an en suite bath. The primary suite upstairs features a king size bed and stunning views of Town Cove with a wonderful en suite bath. The shower feels like an outdoor shower! In addition, the Guest House has an outdoor shower and 6-person hot tub overlooking the Cove. All three homes have AC, WIFI and cable TV. If you feel like leaving your own private resort, good news – two world famous beaches are less than 5 minutes’ drive away, Nauset Beach on the Atlantic or Skaket Beach on Cape Cod Bay. There is nothing that is overlooked at this ideal vacation property for larger groups. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 255.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. This property offers a three night minimum stay during select weeks in May – June and September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®