Vacation rentals in Pleasantville

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Top-rated vacation rentals in Pleasantville

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

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Top guest favorite
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, 126 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 favorite
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, 170 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.

Guest favorite
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, 242 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!

Guest favorite
A bright entryway features light streaming in through the upper floor, illuminating the staircase. Two indoor plants, one on a shelf and another in a pot, add a touch of greenery to the modern decor. The light wooden flooring creates a warm atmosphere.
Home in White Plains
4.96 out of 5 average rating, 118 reviews

Cozy renovated 3bed White Plains Home

Visit beautiful Westchester County, New York and stay in this cozy home located in the vibrant city of White Plains. This newly renovated triplex is only a 12-min walk to North White Plains train station then a 45-minute train ride to Manhattan. Easy access to freeway I-287. Whole Foods, Target, Westchester Mall, and popular restaurants are all within 5 minutes’ drive. Perfect for small families, the space offers 3 bedrooms and 1 full bath across 3 floors with a multiple car parking backyard.

Guest favorite
A spacious living area features a light-colored sectional sofa adorned with a patterned throw and decorative pillows. Soft carpeting covers the floor, enhancing comfort. Natural light floods the space through large windows, illuminating the surrounding decor, including framed photographs on the walls.
Guest suite in Croton-on-Hudson
4.92 out of 5 average rating, 155 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 favorite
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, 207 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.

Top guest favorite
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, 502 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 favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 115 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest favorite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guesthouse in Greenwich
4.95 out of 5 average rating, 109 reviews

The Cottage in Greenwich

Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

Guest favorite
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, 593 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

Top guest favorite
Home in West Side
4.99 out of 5 average rating, 192 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Top guest favorite
A bright living area features a comfortable sofa set against a white wall, paired with a wooden coffee table. Large windows allow natural light to fill the space, while a patterned area rug adds warmth beneath. A modern chair and a small storage unit are also visible.
Cottage in Valhalla
4.96 out of 5 average rating, 330 reviews

Charming private 1BR apt. Easy access to NYC

Location, location, location! Private 1 bedroom unit that is part of a two-unit property. It has its own entrance, kitchen, bath, and off street parking. Walkable to Valhalla Metro North train station. (Has steps and stairs. No children under 12 years old.)

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