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Sleepy Hollow, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Sleepy Hollow, NY

Discover Family-Friendly Vacation Rentals in Sleepy Hollow, NY

The right family vacation rental in Sleepy Hollow, NY makes all the difference, keeping you close to top city attractions.

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.
557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests - Sleepy Hollow, NY
Sleepy Hollow, NY
10/23 – 10/26
$1533/nighttotal: $4599 (3 )

557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests

5 6
apartment , Ossining
This estate is located in Ossining, Westchester, offering proximity to Sleepy Hollow and the scenic autumn landscapes of the surrounding area.
This 6,000 square foot residence accommodates up to 13 guests with 5 bedrooms, 4 bathrooms, a fully equipped kitchen, a pool table, an in-house bar, a swimming pool, a spa, and a garden, perfect for group comfort and entertainment.
Spacious 3br Home / Free Parking / Perfect For Families & Groups - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$1913/nighttotal: $13391 (7 )

Spacious 3br Home / Free Parking / Perfect For Families & Groups

3 2
apartment , White Plains
This 3-bedroom house in White Plains is located in a quiet residential neighborhood, offering convenient access to transportation, dining, and shopping, with Silver Lake Park and Rockefeller State Park Preserve nearby.
This private home accommodates up to 8 guests with 4 queen beds and features a fully equipped kitchen, free onsite parking, and is professionally cleaned with fresh linens and towels provided.
Perfect Family Getaway / 5br Home / 6 Queen Beds / Free Parking - Sleepy Hollow, NY
Sleepy Hollow, NY
10/23 – 10/26
$866/nighttotal: $2598 (3 )

Perfect Family Getaway / 5br Home / 6 Queen Beds / Free Parking

5 6
apartment , Yonkers
This 5-bedroom house in Yonkers' Bryn Mawr neighborhood is located near the Bronx Zoo and Untermyer Gardens Conservancy.
This property offers onsite parking, a fully equipped kitchen, and accommodates up to 12 guests, with air conditioning and internet provided.

Best Sleepy Hollow, NY vacation rentals with parking

Piermont Oasis - Sleepy Hollow, NY
9.8 18 reviews
Sleepy Hollow, NY
09/30 – 10/07
$160/nighttotal: $1120 (7 )

Piermont Oasis

1 2
apartment , Piermont
This Piermont apartment rental offers a private entrance and balcony overlooking mountain greenery, conveniently located near Tallman Mountain State Park and Palisades Interstate Park.
The one-bedroom, one-bathroom unit sleeps two guests and includes WiFi, AC, a kitchenette, and is ideal for exploring nearby attractions like the Tarrytown Music Hall and Rockland Bakery.
3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
8.0 4 reviews
Sleepy Hollow, NY
08/17 – 08/27
$539/nighttotal: $5390 (10 )

3 Mi To Downtown: Spacious White Plains Home

5 3
house , Fairview
This White Plains house rental, located three miles from downtown White Plains and six miles from Westchester County Airport, offers easy access to Manhattanville College, SUNY Purchase, Iona College, and the Palisades Center Mall.
This 3,210-square-foot property boasts five bedrooms, three bathrooms, and accommodates up to 25 guests, featuring a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and free Wi-Fi.
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.
Upscale 1br In Downtown | Kitchen | Gym | Work Space - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$322/nighttotal: $2254 (7 )

Upscale 1br In Downtown | Kitchen | Gym | Work Space

1 2
apartment , White Plains
This White Plains apartment rental is conveniently located near the Galleria mall and Westchester County Center, a short 6-minute walk from the White Plains Metro-North Railroad station.
This 520-square-foot, two-bedroom, one-bathroom unit sleeps three guests and features a full kitchen with dishwasher, in-unit laundry, free WiFi, a smart TV, and access to an on-site fitness center, swimming pool, and concierge services.

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! You've got to visit the Sleepy Hollow Cemetery, where Washington Irving, who wrote 'The Legend of Sleepy Hollow,' is buried. The Old Dutch Church is also a must-see, and it's right next to the cemetery. If you're into art, the Kykuit, the Rockefeller estate, is just a short drive away in nearby Pocantico Hills.
  • 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 walking or biking. It runs along the old aqueduct and offers scenic views of the Hudson River. You can also check out the Sleepy Hollow Historic District, which is perfect for a leisurely stroll. There are also several bike paths around the area, like the Saw Mill River Trail.
  • 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 a great place for outdoor activities. You can go hiking or biking on the trails around the area, like the Rockefeller State Park Preserve. There's also a great golf course at the Sleepy Hollow Country Club. If you're looking for something a little more active, you can go kayaking or canoeing on the Hudson River.
  • What are the best vacation rentals with a pool in Sleepy Hollow, NY?

    The best vacation rental with a pool in Sleepy Hollow, NY is (New To Airbnb) Charming Westchester Townhome.

  • What other towns or cities can be easily accessed from Sleepy Hollow, NY?

    Sleepy Hollow is conveniently located near other popular destinations. You can easily get to Tarrytown, which is just a few miles away. You can also take a short train ride to New York City or a drive to the historic town of Cold Spring, on the opposite side of the Hudson River.
  • 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 offer a range of amenities to make your stay comfortable. You can expect to find things like kitchens, laundry facilities, and Wi-Fi. Many rentals also have outdoor spaces like patios or balconies, and some even have fireplaces. You can also find rentals with unique features like hot tubs or swimming pools.
  • What time of year is best to rent a vacation rental Sleepy Hollow, NY?

    The best time to visit Sleepy Hollow depends on your preferences. If you want to enjoy the fall foliage, September and October are the best months. Spring and summer are also great times to visit, with warmer weather and opportunities for outdoor activities. Just be aware that it can get busy during the peak season.

Destinations nearby

Top Vacation Rentals with Balconies in Sleepy Hollow, NY

Wake up to breathtaking views at these Sleepy Hollow, NY vacation rentals with balconies, perfect for your morning coffee.

3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
9.2 15 reviews
Sleepy Hollow, NY
08/17 – 08/27
$520/nighttotal: $5200 (10 )

3 Mi To Downtown: Spacious White Plains Home

5 3
apartment , Fairview
This White Plains vacation rental, three miles from Downtown White Plains and eight miles from Westchester County Airport, offers easy access to New York City via train.
This 3,210-square-foot home features a spacious seven-bedroom, three-bathroom layout, accommodating up to twelve guests and including amenities such as a private patio, garden with gas grill, garage parking for four vehicles, and free Wi-Fi.
Global Luxury Suites Downtown White Plains - Sleepy Hollow, NY
8.0 238 reviews
Sleepy Hollow, NY
10/23 – 10/26
$857/nighttotal: $2571 (3 )

Global Luxury Suites Downtown White Plains

3 6
apartment , White Plains
The Global Luxury Suites Downtown White Plains is located in the heart of White Plains, just a short distance from Manhattanville College, SUNY Purchase, and Westchester County Airport. This apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers comfortable accommodations, including a fully equipped kitchen, a flat-screen TV, and a private bathroom. Guests can enjoy a range of amenities and activities, such as a seasonal outdoor swimming pool, a fitness center, and a picnic area.
Historic Former Speakeasy 4 Bdrm, Walk To Train And Town: Pleasantville - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$952/nighttotal: $6664 (7 )

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

4 2
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.
3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
Sleepy Hollow, NY
08/17 – 08/27
$560/nighttotal: $5600 (10 )

3 Mi To Downtown: Spacious White Plains Home

1 3
cottage , Fairview
This Fairview cottage is conveniently located within 3 miles of Greenburgh Public Library, Westchester County Center, Pace University Law School, Galleria at White Plains, and Blythedale Children's Hospital.
This smoke-free vacation home features two and a half bathrooms, a fully equipped kitchen with microwave and dishwasher, a private balcony, a private garden with barbecue grills, and free Wi-Fi in public areas; plus, an on-site arcade/game room offers entertainment.

Find the Best Dog-Friendly Vacation Rentals in Sleepy Hollow, NY

Travel with ease to Sleepy Hollow, NY with pet-friendly rentals located near local dog parks and scenic city walks.

Waterfront Luxury In Town - Sleepy Hollow, NY
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.
Convenient Apt: 2 Mi To Sprain Ridge Park! - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$1428/nighttotal: $9996 (7 )

Convenient Apt: 2 Mi To Sprain Ridge Park!

1 2
apartment , Yonkers
This 1-bedroom apartment is located in Yonkers, just a short drive from Sprain Ridge Park, Wave Hill, and Iona College, offering convenient access to outdoor activities and cultural attractions. You can enjoy easy access to Manhattan, with Manhattanville College and Yankee Stadium only 12 miles away.
The apartment is 700 square feet and comfortably accommodates up to 3 guests. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, and parking. You can enjoy the convenience of a private entrance and a comfortable stay with a spacious bedroom and a fully equipped kitchen.
Close To New York City With Bridge View & Parking - Sleepy Hollow, NY
9.6 169 reviews
Sleepy Hollow, NY
09/30 – 10/07
$848/nighttotal: $5936 (7 )

Close To New York City With Bridge View & Parking

1 2
apartment , Sleepy Hollow
This four-bedroom duplex is located just a short walk from Sleepy Hollow's Main Street, offering easy access to shops, restaurants, and attractions. The accommodation boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious home comfortably accommodates up to 10 guests and features a fully equipped kitchen, central air conditioning, a backyard deck, and high-speed Wi-Fi. Guests can enjoy easy access to the Hudson River waterfront, hiking trails, and a variety of local attractions.
Fifa 2026/nyc
Private, Resort-sanctuary - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$3994/nighttotal: $27958 (7 )

Fifa 2026/nyc Private, Resort-sanctuary

5 2
apartment , Old Tappan
This exclusive one-acre private retreat in a prestigious Bergen County neighborhood offers a 35-mile commute to New York City and is conveniently located for access to MetLife Stadium.
This 5,500 sq ft luxury home features 5 bedrooms, 5.5 bathrooms, a chef's kitchen, an oversized family room with three fireplaces, integrated sound and security systems, and a bluestone patio with an outdoor fireplace, accommodating up to 8 guests.
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