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Sleepy Hollow, NY accommodations
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12 Lodgings in Sleepy Hollow, NY

Browse Family Lodgings in Sleepy Hollow, NY

Traveling to Sleepy Hollow, NY with kids? Quality family lodging makes everything easier, keeping city attractions within easy reach.

2br House W/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$1213/nighttotal: $8491 (7 )

2br House W/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2 2
apartment , Yonkers
This 2-bedroom apartment in Yonkers' Bryn Mawr neighborhood offers a private home experience with free onsite parking, located within 2 miles of the Bronx Zoo and Untermyer Gardens Conservancy.
This family-friendly rental accommodates up to 10 guests with a fully equipped kitchen, air conditioning, and internet, providing convenient access to transportation, restaurants, and grocery stores.
Historic Former Speakeasy 4 Bdrm, Walk To Train And Town: Pleasantville - Sleepy Hollow, NY
Sleepy Hollow, NY
08/17 – 08/27
$931/nighttotal: $9310 (10 )

Historic Former Speakeasy 4 Bdrm, Walk To Train And Town: Pleasantville

4 3
castle , Pleasantville
This Pleasantville castle, a short walk from Graham Hills Park and a mile from Rockefeller State Park, offers easy access to Pleasantville's restaurants, farmer's market, and the train to Grand Central Terminal (50-minute ride).
This 4,000-square-foot estate boasts four bedrooms, four bathrooms, and accommodates up to ten guests, featuring a chef's kitchen, spa, and a terrace overlooking mature plantings, plus nearby access to hiking, biking, and shopping at Westchester Mall and the Galleria at White Plains.
Pureheart House, Spacious, 3bdr\n30 Mn From Manhattan. Nyc - Sleepy Hollow, NY
8.8 52 reviews
Sleepy Hollow, NY
10/23 – 10/26
$347/nighttotal: $1041 (3 )

Pureheart House, Spacious, 3bdr\n30 Mn From Manhattan. Nyc

3 6
apartment , Yonkers
This vacation home is located in Northeast Yonkers, just a short distance from the Hudson River Museum and Westchester County Center, in a quiet neighborhood. The house has received excellent user ratings, making it a popular choice for travelers. This three-bedroom home can comfortably accommodate up to six guests, with a spacious living room and dining area. The house features a fully equipped kitchen, a relaxing living room with a balcony, a dedicated workspace, and a stairlift for accessibility.
Westchester Summer: Pool Pet Friendly Events Games - Sleepy Hollow, NY
9.3 28 reviews
Sleepy Hollow, NY
10/23 – 10/26
$1393/nighttotal: $4179 (3 )

Westchester Summer: Pool Pet Friendly Events Games

1 6
house , Ossining
This estate in Ossining, NY, is situated 49 minutes from New York City and 15 minutes from White Plains, with Rockefeller State Park Preserve a 5-minute drive and Sleepy Hollow a 10-minute drive away.
This pet-friendly rental accommodates 13 guests with 5 bedrooms and 4 bathrooms, featuring a custom bar, pool table, arcade games, a seasonal in-ground pool, and private driveway parking for 5 vehicles.

Best Sleepy Hollow, NY lodging with a pool

Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best ones with a pool

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Sleepy Hollow, NY
9.2 7 reviews
Sleepy Hollow, NY
10/23 – 10/26
$1640/nighttotal: $4920 (3 )

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

5 6
apartment , Ossining
This family-friendly vacation home in Ossining is located a 15-minute walk from Sing Sing Correctional Facility and a 12-minute walk from Old Croton Aqueduct State Park.
This spacious 4280 square foot residence offers 5 bedrooms, 4.5 bathrooms, accommodates up to 13 guests, and features a private swimming pool, garden, and covered on-site parking.
Classic Tudor In A Prime Nyc Suburban Location. - Sleepy Hollow, NY
10 5 reviews
Sleepy Hollow, NY
10/23 – 10/26
$2062/nighttotal: $6186 (3 )

Classic Tudor In A Prime Nyc Suburban Location.

4 6
apartment , Scarsdale
This Scarsdale apartment offers a luxurious escape with its serene garden, refreshing swimming pool, and air-conditioned comfort. Its excellent user, location, and cleanliness ratings guarantee a memorable stay.
The apartment boasts four bedrooms and three bathrooms, accommodating up to nine guests. Its amenities include a garden, swimming pool, and air conditioning, ensuring a comfortable and enjoyable stay.
Matt’s Cozy Quarters Near Nyc W/outdoor Living - Sleepy Hollow, NY
Sleepy Hollow, NY
10/23 – 10/26
$493/nighttotal: $1479 (3 )

Matt’s Cozy Quarters Near Nyc W/outdoor Living

1 6
apartment , Orangeburg
This 3-bedroom, 2-bathroom rental home in Orangeburg offers a peaceful residential setting with convenient access to New Jersey via the Palisades Parkway and is located within a mile of local shops and dining.
This pet-friendly apartment features a renovated interior, a seasonal swimming pool open mid-June to early October, a dishwasher, air conditioning, and off-street parking, accommodating up to 10 guests.
Fifa/nyc 
Private, Resort-sanctuary - Sleepy Hollow, NY
Sleepy Hollow, NY
06/26 – 07/04
$2630/nighttotal: $21040 (8 )

Fifa/nyc Private, Resort-sanctuary

5 5
apartment , Norwood
This 5-bedroom, 4-bathroom estate in Norwood offers a private 1.3-acre sanctuary with 25-minute access to New York City via nearby public transportation.
This resort-style residence accommodates up to 10 guests, featuring a swimming pool, air conditioning, a full kitchen with a dishwasher, and dog-friendly amenities.

Frequently Asked Questions about accommodations in Sleepy Hollow, NY

Destinations nearby

Best Sleepy Hollow, NY accommodation with a garden

Mid-century Oasis For Film Crew Shoots/locations - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$5787/nighttotal: $40509 (7 )

Mid-century Oasis For Film Crew Shoots/locations

5 2
apartment , Briarcliff Manor
This 5-bedroom apartment is located in Briarcliff Manor, a short 10-minute drive from the Hudson River and train station, providing easy access to both the tranquility of nature and the excitement of New York City. The apartment is set on 1.75 acres of private land, offering a secluded and peaceful retreat.
The apartment comfortably accommodates 8 guests and features a stylish mid-century modern design with a blend of vintage and modern furniture. Enjoy the outdoor spaces including the sunset terrace, BBQ area, swimming pool, sundeck, and fire pit, as well as the indoor fireplace and access to the vegetable garden and free-range hens.
Clean And Large Family Home In  Nyc Suburbs - Sleepy Hollow, NY
10 7 reviews
Sleepy Hollow, NY
06/26 – 07/04
$2443/nighttotal: $19544 (8 )

Clean And Large Family Home In Nyc Suburbs

5 5
apartment , Scarsdale
This Scarsdale apartment is conveniently located just a short walk from the Metro North train station, offering a quick and easy 45-minute commute to Grand Central Station in New York City. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
This spacious home comfortably accommodates up to 10 guests with its multiple bedrooms and living areas. The apartment provides a fully equipped kitchen, private yard, laundry facilities, and ample storage space for a comfortable and enjoyable stay.
Stylish Tarrytown Studio - Walk To Train & Main St - Sleepy Hollow, NY
9.8 18 reviews
Sleepy Hollow, NY
11/06 – 11/08
$418/nighttotal: $836 (2 )

Stylish Tarrytown Studio - Walk To Train & Main St

1 2
studio , Tarrytown
This Tarrytown apartment rental is centrally located, within a 15-minute walk of the Tarrytown Music Hall and Pierson Park, and less than a mile from historic sites like Philipsburg Manor and the Old Dutch Church of Sleepy Hollow.
This family-friendly unit, sleeping four, boasts a fully equipped kitchen, a jacuzzi, and a private terrace/balcony plus on-site parking and a garden.
Truly Amazing 6-br With Luxury Stay For Worldcup - Sleepy Hollow, NY
10 1 review
Sleepy Hollow, NY
06/26 – 07/04
$3863/nighttotal: $30904 (8 )

Truly Amazing 6-br With Luxury Stay For Worldcup

6 5
apartment , Closter
This spacious 6-bedroom, 5-bathroom apartment in Closter is ideally situated near the Plaza and Palisades Parkway, offering convenient access to local attractions and transportation. With excellent user, location, and cleanliness ratings, this apartment is a top choice for travelers seeking a comfortable and well-equipped accommodation.
The apartment boasts a range of amenities, including a heated pool, covered patio, basketball court, trampoline, gym, and fire pit, providing ample entertainment and relaxation options. The home entertainment system, including a home theater and sound system in every room, enhances the entertainment experience. The apartment's stylish and inviting design, with ceiling fans in every room, creates a comfortable and welcoming atmosphere for guests.

Best Sleepy Hollow, NY accommodation with a kitchen

Upscale Studio In Ny With Kitchen & Serene Setting - Sleepy Hollow, NY
9.1 57 reviews
Sleepy Hollow, NY
08/17 – 08/27
$174/nighttotal: $1740 (10 )

Upscale Studio In Ny With Kitchen & Serene Setting

1 3
apartment , Congers
This Congers, NY studio suite is conveniently located near Rockland Lake State Park and Congers Lake, offering easy access to outdoor recreation and is within driving distance of major Hudson Valley and NYC attractions.
This fully furnished apartment rental boasts a full kitchen, private porch, queen-size bed and sofa bed sleeping up to three guests, and includes on-site parking and a vending machine.
Pool/hottub - Close To Nyc - Sleepy Hollow, NY
9.8 21 reviews
Sleepy Hollow, NY
06/26 – 07/04
$808/nighttotal: $6464 (8 )

Pool/hottub - Close To Nyc

1 5
apartment , Ossining
This charming Tudor-style home is located in Ossining, Westchester, just a short walk from both the Croton/Harmon and Ossining train stations, providing easy access to New York City. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This spacious residence features four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy the private pool and hot tub, the fenced-in yard, and a screened-in porch with a porch swing, perfect for relaxing after a day of exploring Ossining.
Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 Min From Nyc- Ac & Hudson River Views - Sleepy Hollow, NY
10 5 reviews
Sleepy Hollow, NY
09/30 – 10/07
$249/nighttotal: $1743 (7 )

Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 Min From Nyc- Ac & Hudson River Views

1 2
apartment , Dobbs Ferry
This Dobbs Ferry apartment rental boasts a riverfront location, a short drive from the Bronx Zoo (21 minutes) and Westchester County Center (11 minutes).
The one-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen with microwave, in-unit Wi-Fi, air conditioning, and access to a fitness center; nearby attractions include Untermyer Gardens Conservancy and the shops at Ridge Hill.
New 4 Bedroom Designer Home 35 Min From Nyc - Sleepy Hollow, NY
9.7 20 reviews
Sleepy Hollow, NY
08/17 – 08/27
$928/nighttotal: $9280 (10 )

New 4 Bedroom Designer Home 35 Min From Nyc

4 3
apartment , White Plains
This apartment in White Plains is a 15-minute walk from the Metro-North station, making it easy to reach the city in 35 minutes. It's also close to shops and groceries, including Trader Joe's, for convenient access to daily necessities. The apartment boasts excellent ratings for user experience, location, and cleanliness.
This rental features four bedrooms and two bathrooms, accommodating up to five guests. The apartment includes a modern kitchen, a fireplace, and a private garden, perfect for enjoying the outdoors.
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