Holiday houses in Pleasantville

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Top-rated holiday rentals in Pleasantville

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Top Guest favourite
A bright kitchen space features modern appliances, including a black refrigerator and stainless steel stove. A wooden dining table, seating four, is adorned with fresh flowers. Large windows allow natural light to illuminate the room, complemented by simple fixtures and seating.
Guest suite in Mount Kisco
4.98 out of 5 average rating, 122 reviews

Spacious, private retreat 45 mins to NYC

Private, spacious, woodland views, perfect writer's retreat, romantic getaway, or space to chill! Ground-floor apartment in single-family home on 5 acres, 45 mins from NYC. 900 sq. feet of space. Full kitchen, 1 large bedroom, king-size bed & fun bunkbed. Premium bedding, fresh towels, toiletries. Simple, healthy breakfast, coffee, tea, fruit, drinks and snacks provided. 2 miles to Mt Kisco Metro North Station. EV charger. Walk to local nature reserves. 5 mins drive to restaurants and shops.

Guest favourite
A modern living room features a gray sofa set against a wall adorned with a mountain landscape painting. A minimalist rug lies centrally on the floor, complemented by a white refrigerator positioned near an open doorway. Clean lines and neutral colors enhance the space.
Apartment in White Plains
4.92 out of 5 average rating, 168 reviews

Clean, convenient, & close to train & downtown

Beautiful and clean one bedroom unit (with own bathroom, living room, fridge, and kitchenette-no stove) with easy off-street parking! Private entrance and easy walk to the White Plains Metro North Station! Great for those visiting NYC, working at nearby hospitals or companies, commuting into the city, or visiting family in Westchester! Living room sofa can become a futon to sleep on. We have toddlers, but we always try to keep any noise to a minimum, and they usually are in bed by 8 PM.

Top Guest favourite
A stylish living area features a light-colored sofa with patterned cushions. Decorative wall plates and art are displayed above a sleek TV console. Two comfortable chairs, adorned with soft throws, invite relaxation, while a geometric area rug enhances the room's aesthetic.
Apartment in Tarrytown
4.99 out of 5 average rating, 79 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...

Guest favourite
A cozy living area features a large leather sofa adorned with soft, decorative pillows. A wooden coffee table is set with a small platter of snacks and a bottle of wine. A leafy indoor plant and bright natural light enhance the inviting space.
Home in White Plains
4.87 out of 5 average rating, 238 reviews

Bright&Comfy 2bed/1ba in quiet duplex

Bright, comfortable & quiet! Just outside downtown White Plains, this home has a relaxing living space with thoughtful touches. It offers easy accessibility to New York City (35 min Via Metro North) and Westchester (via highways and local buses). The house is set up for WFH, with great wifi via Verizon. It's an easy jump off spot for a fun weekend in Westchester. It comes with a dedicated parking spot, never worry about your vehicle! Bars, restaurants, shopping, groceries are all minutes away!

Top Guest favourite
Two twin beds are positioned side by side, each dressed with patterned bedspreads. A lamp with a decorative base sits on a small bedside table between them. Soft pillows are arranged at the head of each bed, contributing to a relaxed environment.
Apartment in Mount Kisco
4.93 out of 5 average rating, 205 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
A two-story duplex home is presented, featuring a light beige exterior with brick accents. A manicured lawn showcases neat shrubbery and a flowering plant bed. The front steps lead to a covered entryway, flanked by tall trees and complemented by a white picket fence.
Apartment in Pleasantville
4.91 out of 5 average rating, 22 reviews

Cozy Suite near Downtown Pleasantville

Cozy 1-bedroom apartment, includes 1 king bed and 1 full-sized pull-out couch, kitchen, parking, washer, dryer. A single-sized air mattress is also available upon request. Less than a 5-min. walk to downtown Pleasantville, home to many great restaurants/ bars, and the Metro-North train station, which goes directly to Grand Central Station, NYC in 50 min. Close to major highways (Bronx River Pkwy, Major Deegan, Saw Mill Pkwy). Wood & Fire and Southern Table are at the end of the block.

Top Guest favourite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Apartment in Ossining
4.96 out of 5 average rating, 492 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.

Guest favourite
Apartment in Newburgh
4.89 out of 5 average rating, 235 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top Guest favourite
The studio apartment features a queen-sized bed with a teal coverlet and a vibrant red accent chair. Large windows provide natural light, and a writing desk is situated beside the bed. A plush area rug adds warmth to the hardwood flooring.
Guest suite in Pleasantville
4.84 out of 5 average rating, 83 reviews

Charming Studio Centrally Located in Pleasantville

Private Studio Apartment with private entrance. Queen-sized bed + sofa bed. Cozy-space w/ big windows in a big home centrally located in the beautiful small town of Pleasantville. 5 min walk to MetroNorth Train to NYC (45 train ride), Pace University, TONS of bars & restaurants, coffee shops, Jacob Burns Film Center, cute shops. One of the best walking towns in Westchester County. Amazing outdoor activities close by. Friendly host nearby in main house for any questions!

Top Guest favourite
The living area showcases a light-colored sofa adorned with patterned throw pillows, set next to a dark wooden coffee table. A dining area is visible, featuring a kitchen island with seating, and modern appliances can be seen in the well-lit space.
Guesthouse in Mount Kisco
5 out of 5 average rating, 35 reviews

White Cedar Cottage

Tucked away in peaceful Bedford Corners, this renovated 1900s cottage offers charm, comfort, and privacy. Just a short drive to Westchester County Airport (HPN) and popular local spots, only 45 mins to NYC Yet perfectly secluded for a true escape. Relax among the pines, enjoy modern amenities, and you may even spot deer or other wildlife wandering through. Ideal for a romantic getaway, quiet retreat, or a peaceful place to recharge.

Top Guest favourite
A bright dining corner features a small wooden table surrounded by two chairs. Decorative plates adorn the wall above, while natural light enters through the nearby window, illuminating the warm wooden flooring.
Apartment in Ossining
4.95 out of 5 average rating, 38 reviews

Lovely | Private | Historic Home | Walk to Town

Our home is located in the heart of lower Hudson Valley and a quick drive to attractions in neighboring Sleepy Hollow and Croton-on- Hudson. Set in the charming, historic Upper Village neighborhood just a stones throw from downtown Ossining this garden-view apartment occupies part of the second floor of our village colonial and has a private entrance up a set of stairs in our back garden.

Top Guest favourite
A rustic cottage is nestled amidst lush greenery, featuring a weathered wooden exterior and a large window that reflects the surrounding forest. Vibrant foliage and flowers adorn the landscaped yard, creating a peaceful natural setting.
Barn in Mount Kisco
4.91 out of 5 average rating, 592 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

Popular amenities for Pleasantville holiday rentals