Pleasantville, NY Vacation Rentals

Explore 13 vacation rentals, homes, and villas in Pleasantville, NY for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Free Parking 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 $101 per night and featuring up to 6 bedrooms and 4 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.

13 Vacation Rentals in Pleasantville

NYC-Area Escape Near River, Trails & MTA!

Ossining, NY, US
5 Bedrooms 11 Guests
Sep 1 - 4
$334 night

Home Gym | Desk | ~4 Mi to Hudson Hills Golf Course Stay connected to both city energy and river relaxation from this Ossining vacation rental. Spanning 3 levels, this spacious home is 2 miles from the Hudson River and 7 miles from outdoor rec at Croton Gorge Park. Commuting into NYC is simple from Ossining station, putting landmarks like Central Park and Times Square within reach. After a full day out, return to the quiet setting to grill and unwind on the back patio. -- THE PROPERTY -- INDOOR LIVING - House-wide Bluetooth speaker system - Smart TV w/ Disney+, Hulu & Apple TV, DVD player - Dining room, high chair - Board games - Exercise bicycle OUTDOOR LIVING - Spacious yard - Patio w/ charcoal grill/smoker - Outdoor dining area - Gas fire pit ENTERTAINMENT - Mini bar & foosball table - Theater system, popcorn & soda machines - Game area, video games - Karaoke machine KITCHEN - Dishwasher, stove/oven, refrigerator - Microwave, drip coffee pot, coffee grinder, tea kettle, blender - Cooking basics, dishware & flatware, kid's dishware, trash bags & paper towels - Spices ACCESSIBILITY - Stairs required for entry, 3-story home - 1st-floor bedroom & full bathroom PARKING - Driveway (2 vehicles) - Free street parking - RV/trailer parking allowed on-site - Garage not for guest use -- THE LOCATION -- - 1 mile to The Briarcliff Manor - 2 miles to Louis Engel Waterfront Park: Hudson River - 3-7 miles to Gedney Park, Croton Point Park, Croton Gorge Park - 17 miles to Bear Mountain State Park - 32 miles to Manhattan: One World Observatory, Central Park, Times Square, Rockefeller Center, Lincoln Center for the Performing Arts, Grand Central Station -- REST EASY WITH US -- Evolve 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 - Pet friendly w/ $50 fee (+ fees & taxes, max 2 pets) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 3-story home requires stairs for entry. While there is a bedroom and a full bathroom on the 1st floor, stairs are required to access the basement and the 2nd-floor bedrooms and bathroom - There is a kid's cot available for guest use, but sheets and bedding are not provided for it - Your safety matters. This property features 3 exterior security cameras: camera 1 is on the front door facing the exterior front entry, camera 2 is above the garage facing the driveway, and camera 3 is on the back facing the backyard/stairs. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion - The garage is not available for guest use

Furnished New City Home w/ Pool & Game Room

New City, NY, US
6 Bedrooms 13 Guests
Aug 31 - Sep 28
$809 night

Private Basketball Court | Full Kitchen | In-Unit Laundry | Cookout Ready Your elegant Hudson Valley escape awaits at this New City vacation rental! Ideal for groups or families looking to settle in and spread out, this 4,000 sq ft home features a fully equipped kitchen, beautiful backyard, fast WiFi, and Smart TVs. Spend your days playing billiards and board games, splashing in the pool, and enjoying al fresco meals on the deck. Book this unforgettable extended stay today! -- THE PROPERTY -- OUTDOOR LIVING - Private pool (unheated), waterslide, pool toys - Private basketball/tennis court - Deck w/ dining area - Grill INDOOR LIVING - Multiple living areas - Game room w/ pool table, foosball table & board games - Smart TVs - Crib, high chair - Chandeliers, skylights KITCHEN - Stove/oven, refrigerator, microwave - Nespresso Vertuo Plus coffee maker (starter coffee provided), kettle ACCESSIBILITY - 3-level home, stairs required - Bedrooms on upper levels PARKING - Driveway (1 vehicle) -- THE LOCATION -- - 1 mile to New York Pickleball Club & 2 miles to Zukor Park w/ pickleball courts - 3 miles to High Tor State Park, 4 miles to Rockland Lake State Park, 8 miles to Nyack Beach State Park & 11 miles to Bear Mountain State Park - 6 miles to Palisades Center - 13 miles to Lake Welch Beach - 33 miles to Big SNOW American Dream - 37 miles to New York City -- REST EASY WITH US -- Evolve 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 SECURITY CAMERA INFORMATION - 3 exterior devices - Location: doorbell, garage, backyard - Coverage: front entrance, garage entrance, pool

Modern Hastings-On-Hudson Home Near River!

Hastings-on-Hudson, NY, US
2 Bedrooms 4 Guests
Dec 31 - Jan 3
$240 night

Discover the perfect getaway at this 2-bedroom, 1-bath vacation rental in Hastings-On-Hudson! Located just minutes away from top attractions like the Rockefeller State Park Preserve and the Hudson River Museum, this apartment grants you endless opportunities for outdoor adventures and cultural experiences. Be sure to visit New York City to experience buzzing nightlife, delicious eats, stunning parks, and unbeatable attractions. Return to this cozy home to recharge for more New York adventures! -- THE PROPERTY -- 20 Mi to NYC | Near Hiking | Walk to Hudson River | Stainless Steel Appliances | Laptop-Friendly Workspace Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds MAIN FEATURES: Smart TV, dining table, bathtub/shower, deck, seasonal river views KITCHEN: Coffee maker, microwave, stove/oven, dishware & flatware, refrigerator, toaster, cooking basics GENERAL: Free WiFi, linens, hair dryer, central heating, complimentary toiletries, keyless entry, towels, trash bags/paper towels, 3 window A/C units FAQ: Long-term renters on-site, 1 Blink external security camera (facing out), located across from train ACCESSIBILITY: Steps required for access, single-story unit on 1st floor PARKING: Street parking (first-come, first-served) -- THE LOCATION -- ICONIC SIGHTS: Hudson River Museum (3 miles), Bryant Park (20 miles), Times Square (20 miles), Empire State Building (21 miles), Washington Square Park (22 miles), Brooklyn Bridge (25 miles) ART GALLERIES: American Museum of Natural History (18 miles), The Metropolitan Museum of Art (19 miles), The Museum of Modern Art (20 miles) NATURE RETREATS: Draper Park (0.2 miles), Hudson River (0.4 miles), Sugar Pond (1 mile), Sprain Lake Golf Course (4 miles), Van Cortlandt Park (8 miles), Rockefeller State Park Preserve (15 miles), The High Line (20 miles) AIRPORT: LaGuardia Airport (21 miles) -- REST EASY WITH US -- Evolve 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 single-story property is on the 1st floor and requires a flight of stairs to access - NOTE: There is a long-term rental home on-site; residents may be present during your stay - NOTE: This property is located across from train tracks. The train goes to Grand Central Station NYC up to the Hudson Valley along the Hudson River - NOTE: Your safety matters. This property features 1 Blink exterior security camera on the main entrance facing the entryway. The camera is outward facing and does not look into any interior spaces. The camera records video and sound when motion is detected by the device. It records for up to 10 seconds at a time - NOTE: This property is located across from train tracks. The train goes to Grand Central Station NYC up to the Hudson Valley along the Hudson River

Cozy Cottage in Cos Cob

Greenwich, CT, US
1 Bedrooms 2 Guests
Nov 30 - Dec 2
$266 night

Looking for a great deal? Discounts are automatically applied based on your length of stay! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price. Welcome to Cozy Cottage, a charming studio retreat in the heart of Cos Cob. Cos Cob is a lively, village-like part of Greenwich with a community spirit that is at once stylish, fun, and old-fashioned. This cozy cottage offers a prime location just steps from a vibrant aray of restaurants and perfectly located for exploring everything the area has to offer. Inside, you’ll find a meticulously maintained space fearturing a full kitchen with top-notch appliances and a clean, modern design that feels like home. Enjoy the convenience of private parking and access to a fenced-in yard for relaxing. LAYOUT - Large living space with sectional couch and Smart TV - Fully equipped kitchen - Large bedroom with King-sized bed space to move. - Fenced-in patio shared with the sister property but thoughtfully partitioned off to provide you with a sense of privacy AUTHORIZED PETS ONLY Small pets are allowed only with prior authorization; guests must inform us of any pets before arrival. An additional pet fee of $25 per approved pet per day applies after booking (rates negotiable for stays longer than 5 days). Pets are not permitted on furniture or beds. Pets must never be left alone in the home unless crated. Rentee is responsible for cleaning up after their pets. A min. charge for $500 will be applied to bookings with unauthorized pets. Close to Route 1 with everything you will need... Restaurants such as Little Pub Greenwich, Il Pastaficio, Cobs Bread Grocery stores like the wonderful Balducci’s, Whole Foods, etc. Parks such as Cos Cob Park and Montgomery Pinetum Park (great for relaxing, hiking, people watching) Amazing Coffee Shops like Roost and CFCF Coffee Not too far from great shopping on Greenwich Avenue!! Parking in driveway for 1 car, additional parking on street. IMPORTANT BEFORE BOOKING - Primary guest must be 25+ years of age - Family-friendly rental only. No parties, events, or gatherings permitted - Maximum occupancy must be respected. Only registered guests allowed on the property Verification & Booking Policy - Guests may be required to complete ID verification prior to check-in - Access will not be provided until verification is complete - Reservations made under false or misleading information may be canceled without refund Respect for Property & Neighbors - This home is located in a quiet residential area. Guests are expected to respect the property, follow house rules, and be considerate of neighbors at all times Failure to follow these guidelines may result in additional charges or removal from the property without refund

Easy Access to NYC! Sleek Suburban Apartment

Mamaroneck, NY, US
2 Bedrooms 5 Guests
Aug 26 - 28
$105 night

< 1 Mi to Mamaroneck Train Station | 2 Mi to Harbor Island Park Experience the perfect blend of big-city energy, coastal fun, and suburban serenity when you stay at this apartment in the Friendly Village. Explore Larchmont Manor Park or take the nearby train to Grand Central. The choice is yours! When you're ready to unwind, head inside the modern Mamaroneck vacation rental to watch your favorite show. Unlock the best of New York and book this seamless launchpad today! -- THE PROPERTY -- MAIN FEATURES - Living room w/ Smart TV & sectional sofa - Dining table - Vanity KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, toaster - Drip coffee maker (starter coffee provided) - Cooking basics, dishware/flatware ACCESSIBILITY - 2-story unit, flight of exterior stairs to access - Bedrooms on upper level PARKING - Shared driveway (1 vehicle) - Free street parking -- THE LOCATION -- - Located in a residential neighborhood - Quick access to I-95 - 2 miles to Winged Foot Golf Club & 3 miles to Quaker Ridge Golf Club - 4 miles to Larchmont Manor Park - 5 miles to Playland Park - 7 miles to Purchase College - 16 miles to Bronx Zoo - 28 miles to New York City: Times Square, Central Park, Statue of Liberty -- REST EASY WITH US -- Evolve 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 ADDITIONAL INFORMATION - This 2-story unit requires a flight of exterior stairs to access. The bedrooms are located on the upper level - Your safety matters. This property features 1 exterior security camera located at the front door, facing outward toward the front entrance. It does not look into any interior spaces. The camera records video and sound when activated by motion

Belltown Retreat

Stamford, CT, US
3 Bedrooms 6 Guests
Aug 29 - Sep 1
$328 night

HOME AWAY FROM HOME! Belltown Retreat 3 BR/ 2.5 BA/ Sleeps 6 Welcome to this Charming Springdale Colonial home. Located in a friendly neighborhood that is conveniently located near shopping, restaurants, professional offices, banks, a variety of small, locally-owned shops. Easy access to New York City is available through the Springdale train station. Close to downtown Stamford and Mianus River State Park Scenic Reserve. A bright and cheerful home filled with tons of character expected from an older home. Arched doorways welcome you and feature hardwood floors throughout the home, WIFI, a separate laundry room, charming outdoor space. Spacious master suite with queen bed, lounge area, and private bathroom. A sun-filled den perfect for work or play. A/C on upper levels, which cools the entire house. The yard is partially fenced in and the patio is located conveniently right outside the kitchen. Springdale is a section of Stamford that has a small-town feel. Less than a 15-minute drive to several area beaches. Both Sacred Heart University of Fairfield and the University of Bridgeport have conducted classes at "campuses" (rented space for classrooms) in Springdale near the railroad station. Access to Master Bedroom through a bonus 4th bedroom with Single bed. The owner will consider some small dogs with an additional pet fee. Longer than 30 nights please inquire. Master Bedroom: - Queen Size Bed - Private Bathroom - Lounge space - Smart TV - A/C - Master Closet is currently being occupied by Owner Second Bedroom - Queen Size Bed - Shared Bathroom - A/C Third Bedroom - Queen Size Bed - Shared Bathroom - A/C Bonus Bedroom - Twin Bed - Shared Bathroom - Walkthrough room to get to Master Bedroom - A/C AMENITIES - Fully Stocked Kitchen - BRAND NEW DISHWASHER - Outdoor Dining Table - Washer/Dryer - Fully fenced in backyard - Printer Available for use - Living room TV with Apple TV - Smoke Detector and Carbon Monoxide Detector Solar Panels installed December 2021 PROPERTY HIGHLIGHTS: - Minutes to Restaurants - Less than 15 minutes to Stamford and the surrounding town beaches - Easy accesses to New York City Come relax and enjoy what this city has to offer! We take pride in providing sparkling clean properties. Our cleaning has always included sanitizing and disinfecting. During the coronavirus crisis, we will be sure to follow the recommended disinfection protocols. When you visit: please know that everyone is encouraged to socially distance, and when sufficient distance isn’t possible, then please wear a mask. Masks help us to help each other.

Harbor Haven, Apt # 3, 3BR/2BA

Stamford, CT, US
3 Bedrooms 8 Guests
Aug 26 - 28
$376 night

Welcome to Your Spacious Harbor Point Haven – 3 Bedroom Retreat Welcome to one of Stamford’s most loved stays. This beautifully furnished 3-bedroom (4 beds), 2-bathroom home offers the perfect blend of space, comfort, and an unbeatable location in the heart of Harbor Point. Guests consistently rave about the spotless cleanliness, thoughtful touches, and how seamless their stay feels from start to finish. Whether you’re here for work, a family visit, or a weekend getaway, this home is designed to exceed expectations. From the seamless check-in to the spotless, well-maintained space, guests consistently describe their stays here as one of their best. Located in a safe, walkable neighborhood just minutes from Downtown Stamford, the train, and the waterfront, everything you need is right at your doorstep. Unit is on the second floor. THE SPACE - 3 Spacious Bedrooms: Smart TVs, blackout shades for incredibly restful sleep, a guest favorite and plush full-sized beds with fresh linens (one bedroom features two full beds) - Primary Suite: Private bathroom for added comfort and convenience - Guest Room 2: 2 Full sized beds - Guest Room 3: Full sized bed - Second Full Bathroom: Fresh towels, essential toiletries, and modern finishes - Bright, Open Living Area: Comfortable sofa, Smart TV, and plenty of space to relax without ever feeling cramped, ideal for groups who want to spread out comfortably. - Central Heat & A/C: Year-round comfort - High-Speed WiFi: Perfect for work or streaming - Fully Stocked Kitchen: Stainless steel appliances, coffee maker, dishwasher, cookware, and everything you need for an easy stay - Dining Area: Ideal for meals, work, or gathering together - Complimentary Coffee & Tea to start your mornings right - Two Short Flights of Stairs to access the unit - Free Parking for up to 2 cars (no street parking) - Shared Washer & Dryer available for longer stays Perfect for families, groups, or colleagues traveling together who want space, comfort, and convenience. GUEST ACCESS Guests have full access to the entire second-floor Unit 3 apartment. This is a quiet 5-unit building, though you may occasionally see other guests in shared spaces like the stairwell or parking area. LOCATION HIGHLIGHTS 7-minute walk to Stamford Train Station (≈50 minutes to NYC) 5-minute walk to Harbor Point waterfront, restaurants, and boardwalk 15-minute walk to Downtown Stamford (dining, shopping, nightlife) 7-minute walk to Kosciuszko Park & Stamford Harbor 6-minute drive to Stamford Town Center Mall Minutes from Stamford Hospital Quick access to I-95 Guests love how easy it is to get around and how close everything is. EASY ACCESS TO NYC Stamford Metro-North Station – 0.5 miles away Express trains to Grand Central in as little as 50 minutes Frequent service day and night, perfect for commuting or day trips LAST-MINUTE BOOKINGS - Last-minute reservations may require additional guest verification prior to check-in. We look forward to hosting you and providing a stay that’s clean, comfortable, and truly memorable.

Harbor Haven, Apt #2, 2 BR/1BA

Stamford, CT, US
2 Bedrooms 4 Guests
Aug 26 - 28
$247 night

Welcome to Your Stylish Harbor Point Retreat – Comfortable 2 Bedroom Stay Welcome to your ideal Stamford stay in the heart of Harbor Point. This bright, modern 2-bedroom apartment offers the perfect balance of comfort, convenience, and location, making it especially well-suited for longer stays, business travel, or extended visits. Guests love how easy everything is here, from the responsive hosting to the unbeatable location close to the train, waterfront, and downtown. Located on the second floor. THE SPACE - Designed for comfort and simplicity, this home offers everything you need for a relaxed and seamless stay. - Two Comfortable Bedrooms: Premium mattresses, fresh linens, and blackout curtains for restful sleep - Bright Living Area: Stylish and cozy with two Smart TVs (50” + 43” Roku) - Dedicated Workspace: Ideal for remote work or longer stays - Central Heat & A/C (window units): Year-round comfort - High-Speed WiFi - Efficient Kitchen: Fully equipped with essential cookware, modern appliances, and a coffee maker (12 cup drip), perfect for everyday meals and light cooking - Clean, Modern Bathroom: Stocked with fresh towels and essentials - Complimentary Coffee & Tea to start your day - In-Building Washer & Dryer: Especially convenient for extended stays - Free Off-Street Parking for 1 Car - Professionally Cleaned before every guest This space is ideal for couples, small groups, or traveling professionals looking for a comfortable, well-located home base. GUEST ACCESS Guests have full access to the entire apartment during their stay. This is part of a small multi-unit building, so you may occasionally see other guests in shared areas. LOCATION HIGHLIGHTS 7-minute walk to Stamford Train Station (≈50 minutes to NYC) 5-minute walk to Harbor Point waterfront, restaurants, and walking paths 15-minute walk to Downtown Stamford (dining, shopping, nightlife) 7-minute walk to Kosciuszko Park & Stamford Harbor 6-minute drive to Stamford Town Center Mall Quick access to I-95 Perfect for commuting, exploring, or enjoying everything Stamford has to offer. EASY ACCESS TO NYC Stamford Metro-North Station – 0.5 miles away Express trains to Grand Central in as little as 50 minutes Frequent service throughout the day and evening LAST-MINUTE BOOKINGS - Last-minute reservations may require additional guest verification prior to check-in. Whether you’re here for a short visit or an extended stay, this apartment offers a comfortable, well-located space that makes settling in easy.

Walk to Dining & Marina! Modern Stamford Condo

Stamford, CT, US
2 Bedrooms 4 Guests
Oct 7 - Nov 6
$198 night

Remote Work Ready | Easy I-95 Access | Fireside Relaxation Trade the traditional office for coastal convenience at this high-speed Stamford vacation rental, perfectly furnished for long-term stays. Whip up a hearty breakfast in the kitchen, then catch up on work at the desk before heading out to explore. Catch the train into NYC for big city thrills, or walk to Cove Island for a relaxing beach day — the options are endless, and the choice is yours. Secure your extended escape now! -- THE PROPERTY -- INDOOR LIVING - Open floor plan, modern decor - Dedicated workspace - Flat-screen TV, electric fireplace - Central A/C & heating KITCHEN - Stove, oven, dishwasher, microwave - Keurig coffee maker (coffee provided) - Cooking basics - Breakfast bar dining area, dishes & flatware ACCESSIBILITY - Single-story condo - Stairs required to access PARKING - Designated space (2 vehicles) -- THE LOCATION -- - Central location, walking distance to public transportation, convenience/grocery stores, restaurants & parks - Walk to Cove Island: beaches, ice rink, wildlife sanctuary - 2 miles to Downtown Stamford & Stamford Station (train to NYC) - 2 miles to Harbor Point Boardwalk, Mill River Park & West Beach - 5 miles to Stamford Hospital -- REST EASY WITH US -- Evolve 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 - Please observe quiet hours from 10:00 PM to 8:00 AM SECURITY CAMERA INFORMATION - 5 exterior devices - Location: Each side of building, hallway - Coverage: All exteriors, common hallway

Charming Yonkers Retreat - 10 Mi to Central Park!

Yonkers, NY, US
3 Bedrooms 8 Guests
Sep 18 - Oct 18
$200 night

Experience an unforgettable extended stay when at this 3-bedroom, 2-bath vacation rental! The home sits in a quaint neighborhood just a short trip to some of New York's biggest attractions. Visit the Hudson River to kayak, fish, or take a river cruise for the day. See downtown like no other at the One World Observatory, then visit Ripley’s Believe It or Not for family-friendly fun! As the day ends, stroll through Riverdale Park to enjoy more natural wonders that delight all your senses. -- THE PROPERTY -- Family Friendly | Central Location | Free WiFi Perfect for those seeking a peaceful getaway just outside of the Big Apple, this Yonkers retreat offers an ideal location to explore the city! Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed, Twin/Full Bunk Bed | Living Room: Sleeper Sofa INDOOR LIVING: 4 Smart TVs w/ cable, DVD player, fireplace, window AC units, jetted tub KITCHEN: Well-equipped, stove, oven, dishware/flatware, microwave, coffee maker, Crock-Pot, blender, spices, hot water pot, electric cookware, rice cooker, refrigerator GENERAL: Keyless entry, linens/towels, complimentary toiletries, hair dryer, iron/board FAQ: Homeowner on-site, 4 exterior security cameras (facing out), stairs required for access PARKING: Free street parking -- THE LOCATION -- NEARBY: Tibbetts Brook Park (1.8 miles), Van Der Donck Park (2.1 miles), Untermyer Park and Gardens (4.1 miles), LEGOLAND Discovery Center Westchester (5.9 miles), Bronx Zoo (6.5 miles) NYC TO-DOs: Central Park (10.4 miles), Top of The Rock (13.9 miles), St. Patrick’s Cathedral (14.0 miles), Times Square (14.7 miles), Bryant Park (14.7 miles), Rockefeller Center (14.9 miles), The High Line (15.1 miles), Empire State Building (15.1 miles), Washington Square Park (16.5 miles), Brooklyn Bridge (18.1 miles) MUSEUMS: American Museum of Natural History (11.9 miles), Solomon R. Guggenheim Museum (12.3 miles), The Metropolitan Museum of Art (12.6 miles), The Museum of Modern Art (13.7 miles), Whitney Museum of American Art (15.3 miles) AIRPORTS: LaGuardia Airport (14.9 miles), John F. Kennedy International Airport (24.9 miles), Newark Liberty International Airport (29.7 miles) -- REST EASY WITH US -- Evolve 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: The homeowner lives on-site, on the other side of the duplex, and may be present during your stay - NOTE: The property requires stairs and may be difficult for guests with limited mobility - NOTE: Your safety matters. This property features 4 exterior security cameras. The Ring doorbell is located on the front door, camera 2 is in the back of the house facing the back driveway, and cameras 3 & 4 are on either side of the house. The cameras are outward-facing and do not look into interior spaces. The cameras record audio and video but should not infringe on your privacy Licence number: 87-3878500

Vacation Rentals in Pleasantville by Amenities & Features

Get to Know Pleasantville

Pleasantville, New York, is a charming suburban village that offers visitors a serene escape from the hustle and bustle of city life while still being within easy reach of New York City's attractions. This quaint community in Westchester County is known for its friendly atmosphere, picturesque streets, and a variety of cultural and recreational activities that appeal to both families and solo travelers. One of the highlights of Pleasantville is the Jacob Burns Film Center, a cultural hub that showcases independent, documentary, and world cinema. Film enthusiasts can enjoy thought-provoking movies and participate in discussions and educational programs. The center's commitment to the arts makes it a cornerstone of the village's cultural life. For those interested in the outdoors, Pleasantville is surrounded by beautiful natural landscapes. The Rockefeller State Park Preserve offers miles of scenic trails for hiking, horseback riding, and bird watching. The preserve's diverse habitats, including wetlands, woodlands, meadows, and lakes, provide a peaceful setting for nature lovers to explore. Pleasantville's farmers market is a treasure trove for foodies, offering fresh, locally-sourced produce, artisanal cheeses, baked goods, and more. The market not only supports local agriculture but also serves as a gathering place for the community, with live music and special events adding to the vibrant atmosphere. The village's downtown area, with its small-town charm, features a variety of shops, cafes, and restaurants that cater to a range of tastes. From cozy coffee shops to fine dining establishments, Pleasantville's culinary scene is sure to satisfy any palate. For history enthusiasts, the nearby Pocantico Hills and Sleepy Hollow offer a glimpse into the region's past, with historic estates and landmarks that tell the story of the area's development. The iconic Sleepy Hollow Cemetery and the Old Dutch Church are just a short drive away, providing a connection to the rich heritage of the Hudson Valley. Pleasantville also hosts a number of community events throughout the year, including outdoor concerts, festivals, and parades, which showcase the village's strong community spirit and provide entertainment for all ages. In summary, Pleasantville, New York, is a delightful destination that offers a mix of cultural experiences, outdoor adventures, and small-town charm. Its proximity to New York City, combined with its own unique attractions, makes it a worthwhile visit for those looking to enjoy the best of both worlds.
Pleasantville, New York, nestled in the heart of Westchester County, experiences a classic Northeastern climate with four distinct seasons, each offering its own unique appeal. Winter, from December to February, is cold with average temperatures ranging from the low 20s to mid-30s Fahrenheit. Snowfall is common, with the region receiving an average of 25 to 30 inches annually. This season transforms Pleasantville into a winter wonderland, perfect for cozy indoor activities or enjoying the picturesque snow-covered landscapes. Spring, from March to May, brings a gradual warming with temperatures ranging from the mid-40s to high 60s. This season is marked by a mix of rain and sunshine, leading to the blooming of flowers and greening of the area's abundant parks and gardens. The weather can be unpredictable, so layers are recommended. Summer, from June to August, is warm and humid, with temperatures typically in the high 70s to mid-80s. This is the time when Pleasantville truly comes alive, with outdoor events, farmers' markets, and the opportunity to enjoy the many trails and outdoor spaces. Thunderstorms are not uncommon, contributing to the lushness of the region. Autumn, from September to November, is a particularly delightful time to visit Pleasantville. The temperatures cool to a comfortable range of the mid-50s to low 70s, and the humidity drops. The fall foliage is spectacular, with vibrant colors adorning the trees, making it an excellent time for scenic drives or leisurely walks. The most popular weather conditions tend to be in the late spring, when the landscape is in full bloom, and early fall, when the foliage is at its peak and the temperatures are most pleasant. These seasons offer the perfect balance for outdoor activities without the extremes of summer heat or winter cold. For those seeking the quintessential Northeastern experience, Pleasantville in the fall is especially pleasant, with its array of colors and comfortable climate. It's an ideal time for visitors looking to enjoy the natural beauty and charm of the region.
Pleasantville, New York, may not be as well-known as some of the world's major cultural hubs, but it offers a charming and intimate setting for those who delight in the arts, history, and local customs. This quaint village in Westchester County is a haven for cultural enthusiasts looking for a quieter, yet enriching experience. Begin your cultural journey at the Jacob Burns Film Center, a premier venue for independent and documentary films. This cultural institution not only screens a diverse array of films but also hosts Q&A sessions with filmmakers, offering a deeper insight into the cinematic arts. For those interested in history, the Pleasantville Historical Society is a treasure trove of local lore. Housed in a beautifully preserved Victorian building, the society's museum showcases artifacts and exhibits that tell the story of Pleasantville's past, from its early settlement days to the present. Art aficionados will find solace in the local galleries. The Pleasantville art scene may be small, but it is vibrant and welcoming. Galleries like the OSilas Gallery at Concordia College feature rotating exhibitions that highlight both regional and national artists. The gallery also hosts lectures and workshops, providing an interactive experience for visitors. Live music can be enjoyed at a variety of local venues and seasonal events. The Pleasantville Music Festival, for example, is an annual event that brings together a mix of well-known and emerging artists for a day of music and community spirit. Throughout the year, smaller venues and community gatherings offer performances ranging from classical to contemporary genres. Pleasantville's charm extends to its local customs and community events. The Pleasantville Farmers Market, the largest year-round farmers' market in Westchester, is a place where locals and visitors alike can enjoy fresh produce, artisanal foods, and live music, all while engaging with the community. For a taste of local theater, the Arc Stages offers a variety of performances, from contemporary plays to musicals and educational programming. This community-centered space is dedicated to fostering a love for the arts in audiences of all ages. While Pleasantville may not boast the scale of cultural institutions found in larger cities, its dedication to the arts, history, and local customs creates a warm and inviting atmosphere for cultural enthusiasts. It's a place where one can enjoy the richness of culture without the hustle and bustle, making it a delightful destination for those seeking a more relaxed cultural experience.
Pleasantville, New York, is a charming destination that offers a variety of activities for families traveling with children. This quaint village, nestled in Westchester County, provides a peaceful retreat with plenty of kid-friendly attractions. Start your adventure at the Jacob Burns Film Center, where families can enjoy a selection of movies, including educational and child-appropriate films. The center often hosts special events and workshops for young film enthusiasts, making it a great spot for inspiring creativity. For those looking to engage with nature, the Rockefeller State Park Preserve is a short drive away and offers miles of scenic trails perfect for hiking, horseback riding, and bird watching. Children will love the chance to explore the outdoors and may even spot some local wildlife. The Pleasantville Farmers Market, open on Saturdays, is a delightful experience for all ages. Kids can taste fresh, local produce, enjoy live music, and participate in seasonal activities like pumpkin decorating or face painting. If your children are sports enthusiasts, the Pleasantville Recreation Department provides a variety of sports fields and playgrounds. From soccer to baseball, there's ample space for kids to run around and play. The village also has several parks with playgrounds, such as Nannahagan Park, where children can swing, slide, and climb to their hearts' content. For a touch of history, take a short trip to the nearby Van Cortlandt Manor in Croton-on-Hudson. This historic estate offers a glimpse into the past with its beautifully preserved manor house and gardens. They host family-friendly events throughout the year, including the popular Great Jack O'Lantern Blaze during the Halloween season. When it's time to eat, Pleasantville boasts a variety of family-friendly restaurants that cater to even the pickiest of eaters. From classic American diners to pizzerias, there's something to satisfy every appetite. Lastly, for a unique cinematic experience, visit the Westchester's Ridge Hill shopping center in Yonkers, where you'll find LEGOLAND Discovery Center. This indoor LEGO playground features rides, a 4D cinema, and opportunities for kids to build and play with LEGO bricks. Pleasantville and its surrounding areas offer a blend of cultural, recreational, and educational experiences that are sure to delight children and provide a memorable family getaway.
Pleasantville, New York, is a charming village that offers a serene escape into nature for those who seek outdoor adventures and the tranquility of the natural world. Nestled in Westchester County, this picturesque locale is a treasure trove of outdoor activities and natural wonders. The Rockefeller State Park Preserve is a highlight for nature lovers visiting Pleasantville. With over 1,400 acres of varied terrain, the preserve boasts scenic trails that meander through wetlands, woodlands, meadows, and fields. It's an ideal spot for hiking, bird-watching, fishing, and horseback riding. The preserve's carriage roads, designed by John D. Rockefeller Jr., provide a gentle and picturesque path for walkers and equestrians alike. For those who enjoy water-based activities, the nearby Pocantico River offers a peaceful setting for kayaking and canoeing. The gentle flow of the river is perfect for paddlers of all skill levels, and the surrounding foliage provides a lush backdrop, especially during the fall when the leaves turn into a vibrant tapestry of colors. Graham Hills Park is another outdoor haven that should not be missed. This park features challenging trails for mountain biking enthusiasts, with terrain that ranges from steep technical sections to fast, rolling hills. Hikers can also enjoy these trails, which offer a quiet retreat into the woods and the chance to spot local wildlife. For a more leisurely outdoor experience, the Pleasantville Farmers Market, open year-round, allows visitors to connect with the local community and enjoy fresh, locally-sourced produce and artisanal goods. It's a perfect Saturday morning activity, where one can savor organic treats and mingle with friendly vendors and fellow nature lovers. In the heart of Pleasantville, the Jacob Burns Film Center is an unexpected gem for those who appreciate the arts amidst their nature excursions. While not a natural wonder, it provides a cultural complement to the outdoor experiences, showcasing independent and documentary films in a state-of-the-art theater. Lastly, for panoramic views and a touch of history, a visit to the nearby Kensico Dam Plaza is in order. The dam itself is an impressive structure, and the surrounding parkland offers walking paths, picnic areas, and a large open space for various recreational activities. Pleasantville, with its quaint charm and abundance of natural beauty, is a delightful destination for outdoor enthusiasts looking to immerse themselves in nature while still enjoying the comforts and culture of a friendly village atmosphere.
Pleasantville, New York, is a charming suburban village in Westchester County that offers a peaceful retreat with convenient transportation options for visitors. Nestled just about 30 miles north of New York City, it is well-connected to the metropolitan area and beyond. Travelers typically arrive in Pleasantville by car or train. The village is easily accessible via the Taconic State Parkway and the Saw Mill River Parkway, making it a straightforward drive for those coming from other parts of New York State or neighboring states. For those who prefer not to drive, Pleasantville is served by the Metro-North Railroad's Harlem Line, which provides regular service to and from Grand Central Terminal in New York City. The train journey offers a scenic route along the Hudson River and is a popular choice for commuters and visitors alike. Once in Pleasantville, getting around can be quite convenient. The village itself is compact and boasts a walkable downtown area where visitors can explore a variety of shops, restaurants, and the renowned Jacob Burns Film Center on foot. The sidewalks and pedestrian areas are well-maintained, making it pleasant for strolling and soaking in the small-town atmosphere. For destinations that are further afield or for those who prefer not to walk, taxi services and ride-sharing options like Uber and Lyft are available. These can be especially useful for reaching attractions that are outside the village center or for trips to nearby towns and natural areas. Pleasantville also has local bus services provided by the Bee-Line Bus System, which connects it to other parts of Westchester County. This can be a cost-effective way to travel, especially for those looking to explore the wider region without a car. Cycling is another viable option for getting around Pleasantville and the surrounding areas, with several bike-friendly roads and paths available. However, it's important to note that some areas outside the village center may have limited sidewalks or bike lanes, so planning your route in advance is advisable. In summary, Pleasantville offers a variety of transportation options that cater to different preferences. Whether you're arriving by train, driving, or using local transit, you'll find this destination both accessible and navigable. The village's walkable downtown area is a highlight for visitors, providing a quaint and leisurely experience that is emblematic of the charm of Westchester County.

Pleasantville FAQs

Pleasantville is a charming village in Westchester County with a variety of activities to enjoy. Visitors can catch a movie at the historic Jacob Burns Film Center, enjoy outdoor activities at Rockefeller State Park Preserve, explore local history at the Pleasantville Historical Society, or attend a performance at the Arc Stages theater. The village also hosts a popular farmers' market and offers a range of dining options featuring local cuisine.
Pleasantville is easily accessible from New York City by train. You can take the Metro-North Railroad's Harlem Line from Grand Central Terminal to the Pleasantville station. The journey typically takes about an hour. Alternatively, you can drive via the Saw Mill River Parkway or the Taconic State Parkway, which takes about the same amount of time depending on traffic.
Absolutely! Pleasantville boasts a variety of dining options ranging from casual eateries to upscale restaurants. Local favorites include Iron Horse Grill for American cuisine, Mediterraneo for Italian dishes, and the Pleasantville Diner for classic diner fare. There are also several cafes and bakeries for lighter meals or a quick coffee.
Pleasantville is beautiful year-round, but the best times to visit are during the spring and fall. Spring offers blooming flowers and comfortable temperatures, while fall features stunning foliage. The village also has seasonal events such as the Pleasantville Music Festival in the summer and various holiday celebrations in the winter.
While Pleasantville itself has limited accommodation options, there are several hotels and bed & breakfasts in the surrounding area. Nearby towns like White Plains and Tarrytown offer a range of hotels to suit different budgets and preferences. For a more unique experience, you can look for local Airbnb listings in Pleasantville and the surrounding Westchester County.
Yes, Pleasantville is a family-friendly destination. The village has parks and playgrounds, family-friendly restaurants, and activities that cater to all ages. The Jacob Burns Film Center often has programming for children and families, and the farmers' market is a fun outing for everyone. Outdoor spaces like the Rockefeller State Park Preserve provide ample opportunities for hiking and picnicking.
Pleasantville has a quaint downtown area with a variety of shops where you can find gifts, books, clothing, and more. For a larger shopping experience, the nearby Westchester Mall in White Plains offers a wide range of retail stores. Additionally, local artisanal and craft fairs are often held in Pleasantville, providing unique shopping experiences.

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