Vacation rentals in Pleasantville

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.

Charming 3BR Home - Quiet Stay, Close to NYC

Welcome to your White Plains retreat- a beautifully renovated townhouse designed for convenience and a relaxing stay. Perfect for families or small groups, the home features a modern kitchen, three cozy bedrooms, and inviting spaces that truly feel like home. Just a 12-minute walk to North WP Station, you can reach Manhattan in about 45 minutes while still enjoying the restaurants, shops, and charm of Westchester. As Airbnb Superhosts, we’re dedicated to making every stay seamless and memorable.

Charming Studio Centrally Located in Pleasantville

Private Studio Apartment with private entrance. Queen-sized bed + sofa bed. Newly renovated bathroom. 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!

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.

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!

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.

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

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.

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. $19 cleaning with or without pets.

Stylish Tarrytown Studio | Walk to Train & Main St

Modern designer studio 1 block from Main St, 8-min walk to Metro-North (35 mins to NYC). Private entrance, fast Wi-Fi, full kitchen, Queen bed + King sofa bed. Small front yard for a breath of fresh air. Walk to restaurants, cafes, and Hudson River parks. Ideal for couples, solo travelers, and remote workers. Explore charming Tarrytown, Sleepy Hollow, Rockefeller trails, and the Hudson Valley. A stylish, comfortable base for your next getaway!

Clean, Comfy & Convenient. 1Bed Village Apt by MNR

Occupying the entire 2nd floor of a 2 unit home, above a chiropractors office in the heart of the "Big Little Village" Mt Kisco . You will be within a short walk to Northern Westchester Hospital, Metro North train station (for a less than 1 hr ride to Mid-Town Manhattan) along with a slew of high end restaurants, bars, cafes, boutique shops, hiking and outdoor activities abound.

Incredible barn in country setting

Country setting with Vermont feel. Indoor /outdoor fireplaces with large entertainment areas. Small kitchenette, 2 BR. Pull out coach, and sleeping loft . Wifi, CAC, washer/dryer, local hiking w 3 nature preserves nearby. Major estate area. 6 min. from Mt. Kisco train station. One hour NYC. Great local restaurants. Out of the ordinary!