Holiday houses in Pleasantville

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Top-rated holiday rentals in Pleasantville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Home in Ossining

4.85 out of 5 average rating, 151 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.

Guest favourite

Home in White Plains

4.92 out of 5 average rating, 128 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!

Top Guest favourite

Apartment in Tarrytown

4.99 out of 5 average rating, 69 reviews

2 BRs, Easy Walking in Tarrytown and Sleepy Hollow

This special place, newly renovated and lovingly decorated, has a private entrance, off-street parking, and a washer/dryer. Close to everything the Sleepy Hollow/Tarrytown area offers - a short walk to both downtowns, the Metro North train to NYC, Hudson River parks, the Jazz Forum, the Tarrytown Music Hall, a Saturday farmers market. A mile walk to the incomparable Rockefeller Park Preserve, 1.5 miles to Kykuit, 2 miles to Lyndhurst. The list of attractions and destinations goes on and on...

Top Guest favourite

Guest suite in Croton-on-Hudson

4.92 out of 5 average rating, 145 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: No Kitchen!! Drive, walkway & entrance accessible to full size wheelchair (see photos) but bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

Top Guest favourite

Apartment in Mount Kisco

4.93 out of 5 average rating, 191 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mt. Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Guest favourite

Guest suite in White Plains

4.97 out of 5 average rating, 34 reviews

neither near nor far from nyc

Cute, cozy, small apartment on second floor offers a quiet place to relax after a day trip to New York City, hiking or work in the area. Commuter train (40 min to Grand Central Terminal), grocery store, pharmacy, few restaurants, bagel shop are walking distance from the house. Entertainment, restaurants and bars in downtown White Plains (5-10 min ride), hiking and historic sites in Westchester county are short rides away. Come and enjoy the closeness to NYC in a peaceful tree lined area.

Top Guest favourite

Apartment in Ossining

4.96 out of 5 average rating, 454 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Superhost

Tiny home in Chappaqua

4.88 out of 5 average rating, 48 reviews

Cozy tiny log cabin on 13 acres

Tiny rustic cabin located in the woods. Large screen TV and Wi-Fi. No stove but will provide cooktop and toaster. Full bathroom with shower. People love the back deck to enjoy their morning coffee and to watch for wildlife. One bedroom with comfy queen bed and fan. All linens and towels supplied. Please be aware this is a rustic beautiful site. Trails in the back and very close to rail trail. Mini splits will keep you toasty warm in the winter and ice cold in the summer.

Superhost

Guest suite in Ossining

4.73 out of 5 average rating, 60 reviews

Comfortable Studio Apartment

Cozy, private studio apartment in the quiet and historic town of Ossining. The location is close to metro north (Scarborough station), bus stop, shops and some restaurants. The studio is an independent unit attached to the main home. Five minute drive to Phelps Hospital. Ten minutes to PACE university Forty minute train ride to NYC. Close to State Parks, historic Sleepy Hollow, Tarrytown and West-Point. Many hiking options and bike trails nearby.

Top Guest favourite

Apartment in White Plains

5 out of 5 average rating, 6 reviews

Designer 2BR | Luxe Amenities, Gym, Parking

Welcome to your upscale 2-Bedroom retreat at 51 South in downtown White Plains. Enjoy city living with shops, cafes, and transit just steps away. Highlights: • Request a high-floor unit for more light • Deep-clean before every guest • Coffee, fresh linens, & bathroom essentials provided • Co-working Lounge & Quiet Pods • Fitness Center w/ On-Demand Classes • Rooftop Games & Fireplace • Pool with Cabanas & Outdoor Dining (Closed for the season!)

Guest favourite

Guesthouse in Peekskill

4.93 out of 5 average rating, 288 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Top Guest favourite

Barn in Mount Kisco

4.91 out of 5 average rating, 586 reviews

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb