Places to stay in Sleepy Hollow, NY

26 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Sleepy Hollow, NY place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

26 Best places to stay in Sleepy Hollow, NY

Best family friendly Sleepy Hollow, NY lodging

Among the 26 accommodations in Sleepy Hollow, NY, here are the 4 best for families

557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests - Sleepy Hollow, NY
No reviews

557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests

apartment, Ossining
This large property is located in Ossining, Westchester, a short distance from Sleepy Hollow, making it ideal for experiencing the region's autumn colours.
This 557 square meter residence offers five bedrooms, four bathrooms, and can accommodate thirteen guests, featuring a fully equipped kitchen, a custom in-house bar, a pool table, smart TVs, fast WiFi, air conditioning, a swimming pool, a terrace, a garden, a spa, and parking, with pets welcome.
Piermont Landmark House - Garden Suite - Sleepy Hollow, NY
9.9 39 reviews

Piermont Landmark House - Garden Suite

apartment, Piermont
This two-bedroom flat is situated in a historic Greek Revival house, just across the street from the Hudson River in Piermont, a short walk from the town centre and the pier. It has consistently received excellent ratings for location, cleanliness, and user experience.
The apartment can accommodate up to four guests and features a kitchenette with a microwave, mini fridge, and electric kettle. Guests can enjoy a private garden oasis with a patio, lounge chairs, a hammock, and a BBQ, as well as direct access to the Hudson River for scenic walks.
Peaceful 3-bedroom Apartment With Ac In Lovely Yonkers - Sleepy Hollow, NY
No reviews

Peaceful 3-bedroom Apartment With Ac In Lovely Yonkers

apartment, Yonkers
This family-friendly residence in Yonkers' Bryn Mawr district offers convenient access to the Bronx Zoo, situated approximately 5.8 kilometres away, and is a mere 12.2 kilometres from Yankee Stadium.
This spacious 3-bedroom, 2-bathroom house accommodates up to 16 guests and features a dedicated game room with a pool table, foosball, and air hockey, alongside a private backyard with a pergola for outdoor enjoyment.
Beautiful Hudson River Bungalow In Dobbs Ferry - Sleepy Hollow, NY
9.9 221 reviews

Beautiful Hudson River Bungalow In Dobbs Ferry

apartment, Dobbs Ferry
This Dobbs Ferry apartment, a newly renovated property on Main Street, is a seven-minute walk from Dobbs Ferry Metro-North station, offering easy access to Grand Central Terminal in Manhattan and is situated near the Old Croton Aqueduct trail.
The self-catering apartment comprises two bedrooms, a full-size sofa bed, and a full kitchen, sleeping up to four guests and features Netflix, Prime Video, and Wi-Fi.

Best Sleepy Hollow, NY lodgings with a pool

Among the 26 accommodations in Sleepy Hollow, NY, here are the 4 best ones with a pool

Bright, Modern Studio In White Plans - Sleepy Hollow, NY
10 1 review

Bright, Modern Studio In White Plans

apartment, White Plains
This modern studio flat in White Plains' White Place high-rise is conveniently located near shops and public transport, offering easy access to Manhattan, approximately 64km away.
The self-contained apartment, sleeping up to four guests, boasts a kitchenette, bathroom, queen-sized bed, and access to a building with an indoor heated pool, gym, and coworking space.
Luxury 1br In Downtown | Full Kitchen | W&d - Sleepy Hollow, NY
8.4 5 reviews

Luxury 1br In Downtown | Full Kitchen | W&d

apartment, White Plains
This one-bedroom flat is located in downtown White Plains, a short walk from the Galleria at White Plains shopping mall and a 14-minute walk from Westchester County Center. The apartment is conveniently situated near restaurants, shops, and public transport, making it a great base for exploring the area.
The 48 square meter flat comfortably sleeps up to three guests and features a separate living room, dining area, and bedroom. The apartment comes with a range of amenities including a fully equipped kitchen, a private terrace, a shared pool, a fitness centre, and a playground.
Modern 2br In Downtown| Clubhouse + Gym | Parking - Sleepy Hollow, NY
8.8 3 reviews

Modern 2br In Downtown| Clubhouse + Gym | Parking

apartment, White Plains
This White Plains apartment is situated a 6-minute walk from White Plains Metro-North Railroad Station, less than 1.6km from White Plains Hospital Center and Pace University Law School, and within a 15-minute walk of The Galleria at White Plains and Westchester County Center.
The 93 square metre flat offers three bedrooms, two bathrooms, sleeps five guests, and includes a fully equipped kitchen, free Wi-Fi, a swimming pool, fitness centre, concierge service, parking, and is close to numerous shops and entertainment venues.
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Sleepy Hollow, NY
8.6 8 reviews

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok!

apartment, Ossining
This family-friendly holiday home in Ossining is situated a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park.
Boasting 398 square meters of living space, this accommodation accommodates up to 13 guests with 5 bedrooms and 4 bathrooms, featuring a private swimming pool, garden, billiards, and free Wi-Fi, with on-site covered parking and proximity to outdoor activities.

Frequently asked questions about accommodations in Sleepy Hollow, NY

  • What are the must-see sites in or near Sleepy Hollow, NY?

    Sleepy Hollow is brimming with history and charm. You absolutely have to visit the iconic Sleepy Hollow Cemetery, where Washington Irving, the author of The Legend of Sleepy Hollow, is buried. The Old Dutch Church is also a must-see, and you can even take a tour of the Old Dutch Church and Cemetery. If you want to delve deeper into the legend, the Headless Horseman Hayride is a thrilling experience.
  • What are the best accommodations in Sleepy Hollow, NY?

    Among the accommodations in Sleepy Hollow, NY, Castle Hotel & Spa - Luxury Hotel Near Nyc, Relaxing & Great Location & Minutes From New York and Aleida'house On Beautiful Town are the most popular ones.

  • How can travelers reach Sleepy Hollow, NY?

    Sleepy Hollow is easily accessible. The nearest airport is Westchester County Airport, about 30 minutes away. If you're driving, it's about an hour from New York City. The Metro-North Railroad also offers a convenient route from Grand Central Terminal in Manhattan, with the station just a short walk from the village centre.
  • What are the best accommodations with a pool in Sleepy Hollow, NY?

    Castle Hotel & Spa - Luxury Hotel Near Nyc and (New To Airbnb) Charming Westchester Townhome are the best accommodations with a pool in Sleepy Hollow, NY.

  • What outdoor activities can visitors enjoy in and around Sleepy Hollow, NY?

    Sleepy Hollow is a haven for outdoor enthusiasts. You can explore the scenic trails of the Rockefeller State Park Preserve, just a short drive away. The 1600-acre park offers hiking, biking, and even horseback riding. For a more laid-back experience, you can stroll along the Hudson River or enjoy a picnic at the Sleepy Hollow Waterfront Park.
  • What are the best accommodations with a jacuzzi in Sleepy Hollow, NY?

  • When is the ideal time to plan a trip to Sleepy Hollow, NY?

    The best time to visit Sleepy Hollow is during the autumn months, from September to November, when the leaves turn vibrant colours. The village comes alive with Halloween festivities, including the famous Headless Horseman Hayride. Spring and summer are also lovely, with pleasant weather and plenty of outdoor activities.
  • What are the best accommodations for families and kids in Sleepy Hollow, NY?

  • What are the best walking or cycling routes in Sleepy Hollow, NY?

    For a leisurely walk, the Sleepy Hollow Cemetery is a great option. The historic cemetery is beautifully maintained and offers stunning views of the Hudson River. For a longer bike ride, you can follow the Old Croton Aqueduct Trail, which runs for 26 miles along the former aqueduct, offering picturesque scenery and access to several parks.
  • What are the best pet friendly accommodations in Sleepy Hollow, NY?

  • What nearby towns or cities can be explored from Sleepy Hollow, NY?

    Sleepy Hollow is ideally situated for exploring the surrounding area. You can easily visit Tarrytown, just a short drive away, known for its charming shops and restaurants. A bit further afield, you can explore the vibrant city of New York, which is just a short train ride away.
  • What are the best accommodations with parking in Sleepy Hollow, NY?

  • What amenities can travelers expect from accommodations in Sleepy Hollow, NY?

    Sleepy Hollow offers a range of accommodation options, from charming bed and breakfasts to modern hotels. Most accommodations include amenities like Wi-Fi, parking, and breakfast. Some also offer additional amenities like swimming pools, fitness centres, and restaurants. You can find something to suit your budget and preferences.

Popular destinations

Best Sleepy Hollow, NY accommodations with a garden

Hudson River Views: Briarcliff Manor Home W/ Deck - Sleepy Hollow, NY
9.8 14 reviews

Hudson River Views: Briarcliff Manor Home W/ Deck

apartment, Briarcliff Manor
This spacious apartment is located in Briarcliff Manor, just a short distance from the Sleepy Hollow Country Club and Rockefeller State Park Preserve, offering a tranquil setting for your stay. It has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This three-bedroom, four-bathroom apartment spans 386 square metres and can accommodate up to 10 guests, providing ample space for families or groups. The apartment offers a range of amenities, including a game room, home office, gym, and a spacious deck with stunning views of the Hudson River and Palisades Mountains.
Close To New York City With Bridge View & Parking - Sleepy Hollow, NY
No reviews

Close To New York City With Bridge View & Parking

apartment, Sleepy Hollow
This four-bedroom duplex in Tarrytown offers excellent proximity to town sights, the train station, and notable cultural attractions like the Tarrytown Music Hall and Rockefeller Archive Center.
With a floor area of 181 square meters, this accommodation comfortably hosts up to 11 guests and features a microwave oven, dishwasher, air conditioning, and Smart TV, with free parking and scenic bridge/river views.
Classic Tudor In A Prime Nyc Suburban Location. - Sleepy Hollow, NY
10 5 reviews

Classic Tudor In A Prime Nyc Suburban Location.

apartment, Scarsdale
This Scarsdale house, a mile (1.6km) from Scarsdale Metro-North station for easy Manhattan access, offers convenient proximity to top-rated schools and town amenities.
The spacious four-bedroom property sleeps nine, boasting a finished basement with kitchenette and large TV, a private backyard, two driveways, and access to Scarsdale's town pool and tennis courts (membership fees apply for stays over 30 days).
Piermont Jewel - Sleepy Hollow, NY
9.4 353 reviews

Piermont Jewel

apartment, Piermont
This apartment is situated on the main street of Piermont, New York, just a short walk from the Hudson River and the Piermont Pier, offering a charming village atmosphere. It has received excellent ratings for location, cleanliness, and overall user experience.
This cosy flat is ideal for a small group of up to three guests, and is fully equipped with everything you need for a comfortable stay. The apartment includes a kitchen with a fridge, air conditioning, a garden, and parking, making it perfect for exploring the village and enjoying the nearby attractions.

Best Sleepy Hollow, NY accommodations with a kitchen

Nyack Haven - Sleepy Hollow, NY
9.3 248 reviews

Nyack Haven

apartment, Nyack
This two-bedroom flat is conveniently located in Nyack, just a short walk from the village's charming shops, restaurants, and the Hudson River. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The flat is comfortably furnished and can accommodate up to four guests. It is fully equipped with modern amenities including a kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a garden, and parking.
Hudson River Views: Briarcliff Manor Home W/ Deck - Sleepy Hollow, NY
10 2 reviews

Hudson River Views: Briarcliff Manor Home W/ Deck

house, Briarcliff Manor
This Briarcliff Manor estate is situated just 11 miles from The Palisades Center Mall and 14 miles from Manhattanville College, offering stunning Hudson River views and a peaceful setting. The property has received excellent ratings for user experience, location, and cleanliness.
The 3-bedroom home provides ample space for families or groups, with a floor area of 386 square metres and a guest capacity of 10. Enjoy modern amenities such as free Wi-Fi, cable TV, a washing machine, a fully equipped kitchen, a spa, a fitness centre, and a garden.
Prime Luxe 3-br Nyc - Free Parking - Sleepy Hollow, NY
No reviews

Prime Luxe 3-br Nyc - Free Parking

apartment, White Plains
This White Plains flat is located in a residential district, offering easy access to White Plains Hospital Centre, Central Park and the Metropolitan Museum of Art, all within 5 kilometres.
This pet-friendly accommodation for two guests includes a microwave, dishwasher, air conditioning, and on-site laundry facilities, with free parking available.
Charming Dobbs Ferry (Westchester) Victorian Home - Sleepy Hollow, NY
9.4 10 reviews

Charming Dobbs Ferry (Westchester) Victorian Home

apartment, Dobbs Ferry
This Dobbs Ferry apartment, situated opposite Gould Park, is 0.8km from the village centre and 1.6km from the train station, offering easy access to Manhattan via a 35-minute train journey.
Sleeping up to nine guests, this four-bedroom, one-bathroom Victorian house boasts a spacious layout with two king-size and one single bed, a second living area, full kitchen, BBQ, laundry facilities, and ample street parking; it also benefits from a large garden and is available for short or discounted long-term lets.
©2026 cozycozy.com