Holiday 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.

Cozy Guest Suite in Greenwich, 1mi from train

A light-filled studio with private entrance in a newly renovated home. Nestled on a very quiet street, it offers a queen size bed with private bathroom and lounge space (sofa bed) . The space small kitchen amenities include a refrigerator, coffee machine, kettle and microwave, Wi-Fi and private bathroom with shower are additional features. Other things to note As we are a young family looking for total quiet during your stay? We may not be the best hosts for you. Otherwise, please reach out!

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.

5 Min to the Train White Plains/Valhalla apartment

Conveniently located only 5 min drive to Valhalla Train Station and steps from major hospitals this cozy apartment is the ideal find. It is located on the 2nd floor and it foes require you to go up the stairs. You will have parking for 1 car on an outdoor driveway. The apartment has all you need: comfy queen bed and a super comfy couch that is perfect to sleep as well. We don’t have an oven but we have pots, pans and an electric cooktop for your convenience and meal preps. Microwave is there.

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...

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!

Charming 18th-Century Farm Cottage

Lovely 18th-century cottage on our vibrant farm 50 minutes North of NYC. Excellent base for exploring the City & the lower Hudson Valley, or for visiting the area for a work or family event. Inspiring & grounding space for working from home, an ideal retreat for artists & writers! NOTE: Maximum occupancy is 1 couple or 2 individuals. Gatherings w/extra people for the day are not possible. We do not allow children under 12, cottage isn't set up for kids & our property isn't suitable for them.

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.

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!

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.

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.

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)