Holiday rentals in Pocantico Hills

The Hollow Inn at Sleepy Hollow

The Hollow Inn, a charming retreat nestled in the heart of historic Sleepy Hollow—just 45 minutes from NYC and a 15-minute stroll from the Tarrytown train station. Whether you're planning a festive fall getaway with a large family or a peaceful couples’ retreat, this cozy spot is the perfect home base. October is truly magical here, Sleepy Hollow comes alive with Halloween festivities, haunted hayrides, lantern-lit cemetery tours, and more. Book your stay and experience the legend for yourself!

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!

The Westchester Gem. Free Parking! No Cleaning fee

This stylish and modern apt is located in a prime White plains location. It’s right in the hearts of downtown white plains and only about 0.6 miles from White plains station, to make your commute into Manhattan a breeze. The apartment is surrounded by lots of supermarkets including Whole foods which is a stone throw away. There is plethora of restaurants, bars, cafes and shops all within walking distance. The apartment itself is super equipped with everything you would need for a great stay

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

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.

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, never perfect private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (Rustic), yet tastefully curated with eclectic art and furnishings that can change depending on “finds.” Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking.

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!

2 bedroom apartment in Tarrytown/Sleepy Hollow

Hi there! My name is GiGi your Airbnb host:) Your family will be close to everything when you stay at this centrally-located place. Enjoy all wonders of broadway and Main Street the heart of the town. You’re a short walk/ drive away from all the fun, this property is located 5 Minutes away from the train station with just a 45 min train ride to the city. Enjoy the city that never sleeps then come back to a peaceful quiet environment to unwind.