Compare Vacation Rentals & Airbnb in Sleepy Hollow, NY
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12 Rentals and Airbnb in Sleepy Hollow, NY
Sleepy Hollow, NY
23/10 – 26/10
$5583/nighttotal: $16749 (3 )
Fifa 2026/nyc
Private, Resort-sanctuary
5 6
apartment , Old Tappan
This exclusive one-acre luxury residence in Old Tappan, Bergen County, offers a private retreat just 56 kilometres from New York City and is conveniently located for access to Wembley Stadium. This 511 square metre detached house features five bedrooms, five bathrooms, a chef's kitchen with premium appliances, an oversized family room with three fireplaces, and an outdoor bluestone patio with a fireplace, accommodating up to eight guests.
Sleepy Hollow, NY
23/10 – 26/10
$2142/nighttotal: $6426 (3 )
557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests
5 6
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.
Sleepy Hollow, NY
27/06 – 04/07
$352/nighttotal: $2464 (7 )
Welcoming 2-bedroom Apartment In Vibrant Westwood Perfect For Your Stay
2 2
apartment , Westwood
This two-bedroom flat in Westwood provides convenient access to natural areas such as Palisades Interstate Park (approximately 19 kilometres away) and Rockland Lake State Park (approximately 34 kilometres away), as well as major attractions including MetLife Stadium (approximately 37 kilometres away) and American Dream Mall (approximately 35 kilometres away). This pet-friendly accommodation, suitable for up to four guests, offers essential amenities like Wi-Fi, heating, an iron, and a washing machine, with basic toiletries and linens provided for a comfortable stay.
9.9 33 reviews
Sleepy Hollow, NY
30/09 – 07/10
$352/nighttotal: $2464 (7 )
1/2 Block From The Hudson River
1 2
apartment , Nyack
This charming flat is situated on a picturesque street in Nyack, just a short walk from the Hudson River and the town centre with its restaurants and cafes. The area is peaceful and offers a relaxing retreat after exploring the town. The apartment has a private entrance and can accommodate two guests. It features a well-equipped kitchen, a comfortable queen-sized bed, and air conditioning, ensuring a pleasant stay.
Sleepy Hollow, NY
30/09 – 07/10
$293/nighttotal: $2051 (7 )
The Luxe Nook, Premier Studio In Scenic Congers
1 2
studio , Congers
The Luxe Nook studio apartment is located in Congers, New York, 7km from The Palisades Center mall and 24km from Bear Mountain State Park. This self-catering unit sleeps five guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and a flat-screen TV; a private entrance ensures privacy.
10 7 reviews
Sleepy Hollow, NY
27/06 – 04/07
$3276/nighttotal: $22932 (7 )
Clean And Large Family Home In Nyc Suburbs
5 2
apartment , Scarsdale
This spacious apartment is located in Scarsdale, a short walk from the Metro North train station, offering a 45-minute ride to Grand Central Station in NYC. It benefits from excellent user, location and cleanliness ratings. The property is ideal for families or groups of up to 10 guests, and features a private garden, a fully equipped kitchen, laundry facilities and ample storage space. Guests can enjoy a relaxing outdoor space and benefit from a peaceful, residential setting with easy access to shops, restaurants and amenities in Scarsdale Village.
9.8 18 reviews
Sleepy Hollow, NY
27/06 – 04/07
$430/nighttotal: $3010 (7 )
Spring Flowers Coming Up. Plus Great Views Of Croton River Gorge, A Birder Haven
1 2
cottage , Croton-on-Hudson
This Croton-on-Hudson cottage boasts stunning Croton River Gorge views and is situated near the United States Military Academy (distance unspecified) and Sing Sing Correctional Facility. The one-bedroom, two-bathroom property sleeps four guests and includes Wi-Fi, air conditioning, and amenities such as an ironing board and hairdryer; nearby dining options include For The Love Of Chocolate and Lucky Strike (distances unspecified).
9.9 202 reviews
Sleepy Hollow, NY
17/08 – 27/08
$357/nighttotal: $3570 (10 )
Beautiful Hudson River Bungalow In Dobbs Ferry
1 3
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.
Sleepy Hollow, NY
27/06 – 04/07
$378/nighttotal: $2646 (7 )
1br Queen Near Nyc | Trails, Biking & Sauna Bliss
1 2
apartment , Croton-on-Hudson
This aparthotel in Ossining offers a convenient base for exploring Croton-on-Hudson, situated a short distance from Mohansic Golf Course, Captain Lawrence Brewing, Bear Mountain State Park, and the Old Croton Aqueduct State Park. Guests can enjoy complimentary high-speed Wi-Fi, air-conditioned rooms, and an on-site sauna, with easy access to outdoor pursuits such as hiking and biking.
9.7 20 reviews
Sleepy Hollow, NY
17/08 – 27/08
$1297/nighttotal: $12970 (10 )
New 4 Bedroom Designer Home 35 Min From Nyc
4 3
apartment , White Plains
This apartment is located in White Plains, just 1.5 kilometres from the Metro-North station, offering a quick commute to the city and easy access to local shops and amenities. The property has received excellent ratings for cleanliness, location, and user experience. The apartment has four bedrooms, two bathrooms, and can comfortably accommodate five guests. You'll enjoy modern amenities, including a fully equipped kitchen, a fireplace, and a spacious outdoor area with a patio and deck, perfect for relaxing or entertaining.
9.4 10 reviews
Sleepy Hollow, NY
30/09 – 07/10
$291/nighttotal: $2037 (7 )
Nyack- Private Studio Steps From Downtown
1 2
house , Nyack
This Nyack studio apartment is located minutes from Nyack's downtown area, offering easy access to cafes, bakeries, art galleries, Nyack Beach, Memorial Park, and Hook Mountain. The self-contained unit sleeps two guests and features a full kitchen with fridge, freezer, microwave, and dishwasher, plus a private bathroom and convenient workspace; nearby activities include exploring the Hudson River waterfront and hiking Hook Mountain.
Sleepy Hollow, NY
17/08 – 27/08
$371/nighttotal: $3710 (10 )
A Comfortable Cozy Place In The Heart Of Nyack
1 3
apartment , Nyack
This Nyack flat is centrally situated, providing easy access to local amenities and attractions within 1 kilometre of the Hudson River. This private apartment accommodates two guests and features a kitchen, air conditioning, and Wi-Fi, with pets welcome and a high probability of exclusive use.
Best family friendly Sleepy Hollow, NY vacation rentals
Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best family friendly rentals
9.3 28 reviews
Sleepy Hollow, NY
23/10 – 26/10
$1948/nighttotal: $5844 (3 )
Westchester Summer: Pool Pet Friendly Events Games
1 6
house , Ossining
This 6000 sq ft estate in Ossining, New York, is situated just 8 kilometres from White Plains and 49 minutes by train to New York City, offering convenient access to Rockefeller State Park Preserve (800 metres away), Croton Gorge Park (6.4 kilometres away), and Sleepy Hollow (16 kilometres away). This family-friendly, pet-welcoming property accommodates up to 13 guests with 5 bedrooms and 4 bathrooms, featuring a custom bar, pool table, arcade games, a seasonal swimming pool, fully equipped kitchen, fast WiFi, and private parking for 5 vehicles.
Sleepy Hollow, NY
27/06 – 04/07
$2553/nighttotal: $17871 (7 )
Perfect Family Getaway / 5br Home / 6 Queen Beds / Free Parking
5 2
apartment , Yonkers
This expansive five-bedroom residence is situated in Yonkers' Bryn Mawr district, offering convenient access to landmarks such as the Bronx Zoo, located approximately 3.2 kilometres away, and the Untermyer Gardens Conservancy, about 2.4 kilometres distant. This private home accommodates up to 20 guests with six queen beds, featuring a fully equipped kitchen, complimentary on-site parking, and air conditioning, making it a suitable option for families and groups seeking a comfortable stay in Yonkers.
Sleepy Hollow, NY
27/06 – 04/07
$699/nighttotal: $4893 (7 )
Enjoy The Best Of Both Worlds
2 2
apartment , Congers
This two-bedroom flat is located in Congers, just 40 kilometres from New York City and 56 kilometres from Woodbury Commons, offering easy access to Rockland Lake and Bear Mountain, both just minutes away. The surrounding area is peaceful and scenic, with stunning mountain and river views. The flat has three bathrooms and can accommodate up to four guests. It comes with a fully equipped kitchen, air conditioning, a garden, parking for two cars, and internet access. Guests can enjoy a range of activities in the area, including hiking, biking, swimming, and picnicking.
9.6 169 reviews
Sleepy Hollow, NY
23/10 – 26/10
$1363/nighttotal: $4089 (3 )
Close To New York City With Bridge View & Parking
1 6
apartment , Sleepy Hollow
This four-bedroom duplex is located in a lively neighbourhood in Sleepy Hollow, just a short walk from the Metro-North train station and the town's main street. The accommodation has received excellent ratings for location, cleanliness and overall experience. The home is spacious and comfortably accommodates up to 10 guests. It comes equipped with modern amenities like high-speed Wi-Fi, smart TVs, a fully equipped kitchen and a private garden. Guests can enjoy easy access to local attractions, activities and restaurants.
Best Sleepy Hollow, NY vacation rentals with parking
Sleepy Hollow, NY
23/10 – 26/10
$1185/nighttotal: $3555 (3 )
Spacious 3br Home / Free Parking / Perfect For Families & Groups
3 6
apartment , White Plains
This three-bedroom flat in White Plains is located in a peaceful residential area, offering easy access to amenities and attractions such as Bowlero White Plains and Silver Lake Park, situated approximately 1.6 kilometres away. This private residence accommodates up to 16 guests with four queen beds, featuring a fully equipped kitchen, air conditioning, complimentary on-site parking, and is professionally cleaned with fresh linens and towels provided.
9.2 15 reviews
Sleepy Hollow, NY
30/09 – 07/10
$898/nighttotal: $6286 (7 )
3 Mi To Downtown: Spacious White Plains Home
5 2
apartment , Fairview
This Fairview property, a seven-bedroom, three-bathroom house, is situated 4.8 kilometres from White Plains city centre, 3.2 kilometres from the Bronx River Greenway, and offers easy access to New York City (51.5 kilometres away). The 298 square metre dwelling boasts a spacious layout sleeping up to twelve guests, featuring a private patio, garden with gas grill, garage parking for four vehicles, plus Smart TVs, a washer/dryer, and complimentary toiletries.
Sleepy Hollow, NY
27/06 – 04/07
$2092/nighttotal: $14644 (7 )
Convenient Apt: 2 Mi To Sprain Ridge Park!
1 2
apartment , Yonkers
This Northeast Yonkers flat is conveniently located within 5km of NewYork-Presbyterian Westchester Hospital and Sarah Lawrence College, and within 10km of Legoland Discovery Centre Westchester and Empire City Casino. This 65 square metre one-bedroom apartment sleeps two, offering free Wi-Fi, on-site parking, a fully equipped kitchen, and amenities including a TV, coffee maker, and hairdryer.
Sleepy Hollow, NY
27/06 – 04/07
$345/nighttotal: $2415 (7 )
Cozy Apartment To Relax - Apartment "A"
2 2
apartment , Yonkers
This flat offers a prime Yonkers location, just 3 minutes by car from Untermyer Gardens Conservancy and 5 minutes from Van Cortlandt Park, with convenient access to the Westchester County Center and the Metropolitan Museum of Art. This property provides complimentary Wi-Fi, air conditioning, a fully equipped kitchen with a fridge and microwave, and a private terrace, making it ideal for exploring attractions like the Bronx Zoo and Yankee Stadium.
Frequently Asked Questions about vacation rentals in Sleepy Hollow, NY
What are some interesting places to visit in or near Sleepy Hollow, NY?
Sleepy Hollow is packed with history and charm. You've got the iconic Sleepy Hollow Cemetery, where Washington Irving is buried, and the Old Dutch Church, where he drew inspiration for his famous story. And if you're into art, the Kykuit, the Rockefeller estate, is a must-see, just a short drive away.
What are the best Airbnb and vacation rentals in Sleepy Hollow, NY?
Which walking or cycling routes are the best in Sleepy Hollow, NY?
The Old Croton Aqueduct Trail is a great option for both walking and cycling, offering scenic views of the Hudson River. You can also take a stroll along the Pocantico River Walk, which runs alongside the river and offers a peaceful escape from the hustle and bustle of the town.
What are the most popular Airbnbs in Sleepy Hollow, NY?
What sports or outdoor activites can visitors enjoy in and around Sleepy Hollow, NY?
Sleepy Hollow is perfect for outdoor enthusiasts. You can go kayaking or canoeing on the Hudson River, or explore the scenic trails at Rockefeller State Park Preserve. For a more leisurely activity, try a round of golf at the Sleepy Hollow Country Club.
What are the best vacation rentals with a pool in Sleepy Hollow, NY?
What other towns or cities can be easily accessed from Sleepy Hollow, NY?
Sleepy Hollow is ideally located near other fascinating destinations. You can easily reach Tarrytown, with its historic charm and waterfront restaurants, or head to the vibrant city of New York City, just a short train ride away.
What are the best rentals for families and kids in Sleepy Hollow, NY?
What amenities are commonly available in vacation rentals in Sleepy Hollow, NY?
Vacation rentals in Sleepy Hollow usually come equipped with modern amenities like Wi-Fi, a fully equipped kitchen, and comfortable bedrooms. Many also offer outdoor spaces like a patio or balcony for enjoying the fresh air.
What time of year is best to rent a vacation rental Sleepy Hollow, NY?
The best time to rent a vacation rental in Sleepy Hollow depends on what you're looking for. Spring and autumn offer pleasant weather and vibrant foliage, while summer is ideal for outdoor activities. If you're looking for a more peaceful experience, consider visiting during the off-season.
What are the local dishes in Sleepy Hollow, NY region?
The Hudson Valley is known for its fresh, seasonal produce, so you'll find plenty of farm-to-table restaurants in Sleepy Hollow. Try some local specialties like apple pie, Hudson Valley foie gras, or a hearty dish with local mushrooms. And don't forget to sample some of the region's award-winning craft beers and wines!
Destinations nearby
Best Sleepy Hollow, NY vacation rentals with a balcony
Sleepy Hollow, NY
27/06 – 04/07
$516/nighttotal: $3612 (7 )
Beautiful Apartment 1 In Great Pleasantville, Ny
3 2
apartment , Pleasantville
This three-bedroom flat in Pleasantville offers convenient access to Captain Lawrence Brewing Company, Bowlero White Plains, and is a short drive to Rockefeller State Park Preserve and the Audubon Center. This accommodation comfortably sleeps six guests and provides essential amenities including air conditioning and Wi-Fi, with easy access to family attractions such as the Westchester Skating Academy and Legoland Discovery Center Westchester.
9.7 292 reviews
Sleepy Hollow, NY
23/10 – 26/10
$1541/nighttotal: $4623 (3 )
Modern 4bd/3ba W/parking & Deck & 29 Min>nyc
4 6
apartment , Hastings-on-Hudson
This family-friendly house is located in Yonkers, a short drive from Hastings-on-Hudson and close to attractions like Untermyer Gardens Conservancy and the Hudson River Museum. The property has excellent user, location, and cleanliness ratings. The house has three bedrooms and is 102 square metres in size. It offers a range of amenities including a swimming pool, tennis court, and a fully equipped kitchen, perfect for a comfortable and enjoyable stay.
8.0 4 reviews
Sleepy Hollow, NY
17/08 – 27/08
$754/nighttotal: $7540 (10 )
3 Mi To Downtown: Spacious White Plains Home
5 3
house , Fairview
This spacious five-bedroom house in White Plains, Fairview, is situated 5km from White Plains city centre, offering easy access to Manhattanville College (9km), SUNY Purchase (11km), Iona College (18km), and Westchester County Airport (10km). The 298 square metre property boasts three bathrooms, a fully equipped kitchen including a dishwasher and microwave, private parking, a terrace, garden, free Wi-Fi, and comfortably accommodates up to 25 guests.
9.2 7 reviews
Sleepy Hollow, NY
23/10 – 26/10
$2293/nighttotal: $6879 (3 )
Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok!
5 6
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.
Best pet friendly Sleepy Hollow, NY vacation rentals
Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best pet friendly rentals
9.9 74 reviews
Sleepy Hollow, NY
30/09 – 07/10
$979/nighttotal: $6853 (7 )
Waterfront Luxury In Town
1 2
apartment , Piermont
This waterfront flat is located in Piermont, a charming village just 15 minutes by car from the train station offering easy access to New York City. The property has received excellent reviews for its location, cleanliness, and user experience. The apartment features four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy the spacious living area, the fully equipped kitchen, and the private outdoor space including decks, patio, and a yard stretching to the river.
8.0 3 reviews
Sleepy Hollow, NY
27/06 – 04/07
$367/nighttotal: $2569 (7 )
Fully Furnished, Cozy 1br In White Plains
1 2
resort , White Plains
This apartment is situated in Downtown White Plains, a short train journey from Manhattan and a quick drive up the Hudson River, making it a convenient base for exploring the area. It has received excellent ratings for location, cleanliness, and overall user experience. The flat is a one-bedroom, one-bathroom property with a capacity for three guests. Guests can enjoy a range of amenities, including a swimming pool, fitness centre, and a garden, as well as a fully equipped kitchen and laundry facilities.
Sleepy Hollow, NY
27/06 – 04/07
$1646/nighttotal: $11522 (7 )
Stylish 3br Home Game Room Free Parking Sleeps 16
3 2
apartment , White Plains
This three-bedroom, two-bathroom flat in White Plains, conveniently situated within 2 kilometres of cultural sites such as the Westchester Broadway Theatre and Rockefeller Archive Center, offers ample space for up to 16 guests. This White Plains rental, ideal for large groups and families, features five queen beds, a dedicated game room, free on-site parking, and a fully equipped kitchen, ensuring a comfortable and entertaining stay for all.
Sleepy Hollow, NY
27/06 – 04/07
$1996/nighttotal: $13972 (7 )
Convenient Apt: 2 Mi To Sprain Ridge Park!
1 2
apartment , Yonkers
This one-bedroom flat is conveniently located in Yonkers, just 3 kilometres from Sprain Ridge Park, 16 kilometres from the Bronx Zoo and 19 kilometres from Manhattanville College. The surrounding area offers easy access to major highways and public transport, making it a great base for exploring the region. The 65 square metre flat comfortably sleeps up to three guests and features a fully equipped kitchen, a private entrance, air conditioning, free Wi-Fi and parking. Enjoy the convenience of having a fridge, a microwave oven, towels and bed linen provided, as well as the added bonus of being pet-friendly.