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12 Lodgings in Sleepy Hollow, NY
9.7 33 reviews
Sleepy Hollow, NY
11/06 – 11/08
$466/nighttotal: $932 (2 )
Comfortable Cottage
1 2
apartment , Briarcliff Manor
This Briarcliff Manor cottage, located directly on the North County Trailway, offers easy access to the Rockefeller State Park Preserve, Stone Barns Center, and is a 2.5-mile walk or 10-minute Uber ride from the train station for convenient NYC access. Sleeping five guests comfortably, this three-bedroom, one-bathroom house boasts a spacious dining room, fenced yard with a swing, basement laundry, smart TV, fireplace, sunroom, and full kitchen with dishwasher; plus, enjoy nearby hiking, biking, and farm visits.
9.9 20 reviews
Sleepy Hollow, NY
08/17 – 08/27
$529/nighttotal: $5290 (10 )
Stylish, Cozy 2 Br Pied-á-terre
1 3
apartment , Tarrytown
This Tarrytown apartment is conveniently located near the Old Croton Aqueduct Trail, a short walk from Main Street's shops and cafes, and a 12-minute walk from the Metro-North Tarrytown train station offering easy access to Manhattan. The newly renovated unit features a fully equipped kitchen, in-unit laundry, a 65-inch smart TV, and sleeps four guests, perfect for exploring Tarrytown and its surrounding attractions.
Sleepy Hollow, NY
06/27 – 07/04
$166/nighttotal: $1162 (7 )
2 Bed 2 Bath Near Metro North.
2 2
apartment , White Plains
This two-bedroom, one-bathroom apartment in White Plains offers convenient access to local attractions and amenities, though precise distances require further clarification. The 2-bedroom rental sleeps 4-5 guests comfortably and includes a kitchen, air conditioning, on-site fitness center, and parking.
9.8 244 reviews
Sleepy Hollow, NY
09/30 – 10/07
$140/nighttotal: $980 (7 )
Private Charming Studio Efficiency
1 2
apartment , Dobbs Ferry
This studio apartment is located in Dobbs Ferry, a short walk from the train station and within easy reach of restaurants like Sushi Mike's and The Parlor. Guests consistently rate this property as excellent for location, cleanliness, and overall experience. This basement apartment offers a private entrance and is ideal for solo travelers, couples, or business travelers. The studio features a fully equipped kitchen with a refrigerator, coffee pot, toaster oven, and microwave, making it easy to prepare meals.
9.9 74 reviews
Sleepy Hollow, NY
09/30 – 10/07
$700/nighttotal: $4900 (7 )
Waterfront Luxury In Town
1 2
apartment , Piermont
This waterfront apartment in Piermont is just minutes from the downtown area and a quick 15-minute drive to the NYC train station, offering easy access to both Piermont's charming shops and restaurants and the excitement of the city. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The apartment features four bedrooms and two bathrooms, comfortably accommodating up to eight guests. You'll enjoy a spacious open floor plan with a large living area, dining room, and kitchen, as well as a private outdoor space with decks, a patio, and a yard directly on the waterfront.
9.7 34 reviews
Sleepy Hollow, NY
11/06 – 11/08
$185/nighttotal: $370 (2 )
Private & Cozy 1 Bedroom Apartment In White Plains
1 2
apartment , Fairview
This one-bedroom Fairview basement apartment is conveniently located two miles from the Metro-North train station, offering easy access to NYC and downtown White Plains. The unit, sleeping two, features a fully equipped kitchen (excluding stove), outdoor dining area with propane grill and fire pit, and is close to White Plains Hospital and the County Center.
9.2 29 reviews
Sleepy Hollow, NY
08/17 – 08/27
$494/nighttotal: $4940 (10 )
3 Mi To Downtown: Spacious White Plains Home
5 3
apartment , Fairview
This spacious White Plains house, near Westchester County's largest walkable downtown area, provides easy access to White Plains and convenient train access to New York City. The 3212-square-foot, five-bedroom, 2.5-bathroom home sleeps 13, features a fully equipped kitchen, a private patio and garden, and parking for four vehicles, plus amenities like Smart TVs and a washer/dryer.
8.0 4 reviews
Sleepy Hollow, NY
06/26 – 07/04
$945/nighttotal: $7560 (8 )
Private Suite In Scarsdale Near Nyc & White Plains
1 5
apartment , Greenville
This apartment is an excellent choice for travelers visiting Greenville. It's conveniently located in a safe and quiet neighborhood, within walking distance of popular attractions. The apartment has received very good ratings for its cleanliness, location, and user experience. The apartment has one bedroom, one bathroom, and can accommodate up to 10 guests. It features a fully equipped kitchen, air conditioning, internet, and parking. Guests can enjoy the convenience of being close to restaurants, shops, and entertainment options.
Sleepy Hollow, NY
06/27 – 07/04
$252/nighttotal: $1764 (7 )
Welcoming 2-bedroom Apartment In Vibrant Westwood Perfect For Your Stay
2 2
apartment , Westwood
This 2-bedroom, 1-bathroom apartment in Westwood offers convenient access to outdoor recreation, with Palisades Interstate Park 12 miles away and Rockland Lake State Park 21 miles away, while also being a short drive to entertainment hubs like MetLife Stadium (23 miles) and American Dream mall (22 miles). This pet-friendly unit accommodates up to 4 guests and includes essential amenities such as Wi-Fi, heating, a washing machine, and linens for a comfortable stay.
9.9 207 reviews
Sleepy Hollow, NY
11/06 – 11/08
$417/nighttotal: $834 (2 )
Chic Vintage Cottage In Artsy Village Of Nyack
2 2
apartment , Nyack
This charming 1929 cottage sits just one block from Main Street in Nyack Village, putting you within easy walking distance of the town's restaurants, shops, and cultural attractions. Guests consistently rate the cottage as excellent for its location, cleanliness, and overall experience. The cottage features an open floor plan with a woodburning stove, perfect for cozy evenings, and can comfortably accommodate up to four guests. You'll also find a well-equipped kitchen, a private yard with a fire pit lounge, and a four-season sunroom, making it a great place to relax and unwind after a day of exploring.
8.0 2 reviews
Sleepy Hollow, NY
06/27 – 07/04
$265/nighttotal: $1855 (7 )
Polished 1br W/ Accessible Room Features + Sauna
1 2
apartment , Ossining
This ADA-friendly studio apartment in Ossining, NY, offers a serene Hudson Valley escape, conveniently located minutes from New York City and near attractions like Croton Gorge Park and Rockefeller State Park Preserve. This accommodation features a queen guestroom with a roll-in shower, complimentary Wi-Fi, air conditioning, a sauna, fitness center, and on-site parking, accommodating up to two guests.
9.0 6 reviews
Sleepy Hollow, NY
10/23 – 10/26
$820/nighttotal: $2460 (3 )
Castle In The Sky ! Beautifully Renovated Victorian One Block From Main St.
4 6
apartment , Nyack
This Nyack vacation rental is a 4-bedroom, 4-bathroom house located within a 15-minute walk of the Edward Hopper House Art Center and Nyack Hospital, and near Blauvelt State Park and the Rockland Center for the Arts. This 8-guest home features in-unit laundry, essential amenities like a hair dryer and ironing board, and is ideally situated for exploring Nyack's attractions and public transportation.
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.
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.
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.
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.
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
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.
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.
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.
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
What outdoor activities can visitors enjoy in and around Sleepy Hollow, NY?
Sleepy Hollow is great for walking and biking. The Old Croton Aqueduct Trail is a beautiful 26-mile paved path perfect for a leisurely stroll or bike ride. You can also enjoy kayaking or canoeing on the Hudson River.
What are the best accommodations 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 in the fall, when the leaves change color. You can also enjoy the Halloween season, with lots of events and activities. Spring and summer are also pleasant times to visit, with warmer temperatures and longer days.
What are the best accommodations with a pool in Sleepy Hollow, NY?
What are the best walking or cycling routes in Sleepy Hollow, NY?
The Old Croton Aqueduct Trail is a great option for a leisurely walk or bike ride. It runs through Sleepy Hollow and offers beautiful views of the Hudson River. You can also walk or bike along the riverfront in Sleepy Hollow, enjoying views of the Tappan Zee Bridge.
What are the best accommodations with a jacuzzi in Sleepy Hollow, NY?
What nearby towns or cities can be explored from Sleepy Hollow, NY?
Tarrytown is just a short walk from Sleepy Hollow and is worth exploring. You can also easily visit nearby cities like New York City, Yonkers, and White Plains. If you want to experience a bit of history, visit the historic town of Croton-on-Hudson.
What are the best accommodations for families and kids in Sleepy Hollow, NY?
Best Sleepy Hollow, NY accommodation with a garden
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.
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.
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.
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
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.
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.
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.
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.