
House vacation rentals in Pleasantville
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Top-rated house rentals in Pleasantville
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1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!
4.91 out of 5 average rating, 146 reviews
Spacious 3b/3b Mediterranean in White Plains
Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!
4.91 out of 5 average rating, 178 reviews
Lower Hudson Valley Idyllic Retreat
Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.
4.84 out of 5 average rating, 170 reviews
Modern 3BD West Point USMA House w/ HotTub!
Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!
4.99 out of 5 average rating, 116 reviews
Entire Home, Private Indoor Pool
This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.
4.81 out of 5 average rating, 136 reviews
Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC
4.99 out of 5 average rating, 190 reviews
Panoramic Lakeviews & Lush Garden | Beach Access
Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features hundreds of plants and a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. Guests get access to a private community beach. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, fireplace, smart TV, record player and board games.
5.0 out of 5 average rating, 227 reviews
Entire 4BR House, Walk to Train! Yard + Parking
Enjoy the 4BR/2BA house to yourself in one of Westchester’s most family-friendly communities, <40 min from NYC. Ideal for families (dog friendly, 1 per stay), relocations and longer stays, with a fenced yard, parking, fast Wi-Fi, washer/dryer and kid essentials (a crib, bassinet & more). Walk to Metro-North (13 min), stores, restaurants and Mamaroneck Ave. Kids will love the fenced yard and Florence Park down the block, with a playground, basketball and tennis. Need a longer stay? Ask us!
4.99 out of 5 average rating, 114 reviews
Beautiful & Fun Waterfront Duplex on the Hudson
Enjoy a getaway to this charming historic waterfront home. Sip a glass of wine, a cup of Joe, or a refreshing cool drink from the 36 ft deck overlooking the Hudson River and Mario Cuomo Bridge beautifully lit up each evening. **PLEASE read everything in the description of "The Space" and "Other Things to Note" before booking. Thank you! Check out my "GUIDEBOOK" for my favorite picks including entertainment, shopping, eateries, and more. Non shedding pets welcome with additional fee $150.
4.86 out of 5 average rating, 165 reviews
Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.
4.94 out of 5 average rating, 143 reviews
Cozy getaway 1 hr from NYC!
This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.
4.91 out of 5 average rating, 186 reviews
Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC
Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225
4.97 out of 5 average rating, 116 reviewsPopular amenities for Pleasantville house rentals
House rentals with a pool

Lake Views | Pool + Hot Tub | 1hr NYC | Ski Access
4.92 out of 5 average rating, 118 reviews
Cozy, Modern Retreat in the Woods of Cold Spring
4.95 out of 5 average rating, 179 reviews
Historic Cornwall Farmhouse w/ Sauna & Hot Tub
5.0 out of 5 average rating, 107 reviews
Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
4.92 out of 5 average rating, 181 reviews
Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
4.96 out of 5 average rating, 141 reviews
Midcentury Modern ZenHouse Sculptor Studio
4.96 out of 5 average rating, 270 reviews
Modern 3 Bedroom Apartment Oasis PRIME Location
4.95 out of 5 average rating, 127 reviews
Legoland Mt Peter 3BR Pool Theater Hot Tub 1Pet
4.96 out of 5 average rating, 108 reviewsWeekly house rentals

Family Cottage with 4 King Beds and Fire Pit
4.98 out of 5 average rating, 147 reviews
Hudson Valley Mountaintop Riverview
4.93 out of 5 average rating, 185 reviews
Crystal Wave LakeHouse
4.91 out of 5 average rating, 150 reviews
Peaceful & Spacious Retreat
4.96 out of 5 average rating, 179 reviews
Home in Cold Spring- Farm Stay!
4.99 out of 5 average rating, 104 reviews
Spacious, bright 5 bedroom house near West Point
4.99 out of 5 average rating, 214 reviews
Bright & Modern Victorian in NY Suburbs
4.98 out of 5 average rating, 152 reviews
Charming 3BR Walk to Town & Train
5.0 out of 5 average rating, 17 reviewsPrivate house rentals

The Hollow Inn at Sleepy Hollow
4.95 out of 5 average rating, 21 reviews
Elegant Hideaway: Cozy Cottage in Katonah, NY
5.0 out of 5 average rating, 12 reviews
1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres
4.89 out of 5 average rating, 71 reviews
A nice place to getaway
4.92 out of 5 average rating, 84 reviews
Fox Run 4 bedroom Private House
4.93 out of 5 average rating, 80 reviews
Comfortable Mid-Century on Quiet Country Road
5.0 out of 5 average rating, 79 reviews
Beachfront Home on the Hudson w/ Amazing Views!
4.94 out of 5 average rating, 80 reviews
Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC
4.93 out of 5 average rating, 71 reviewsDestinations to explore
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