Compare best Airbnb in Sleepy Hollow, NY from 100+ providers!

12 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Sleepy Hollow, NY vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

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.
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.
Perfect Family Getaway / 5br Home / 6 Queen Beds / Free Parking - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$1827/nightTotal: $12789 (7 )

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

5 2
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.
Relaxing & Great Location & Minutes From New York - Sleepy Hollow, NY
9.6 173 reviews
Sleepy Hollow, NY
08/08 – 08/13
$606/nightTotal: $3030 (5 )

Relaxing & Great Location & Minutes From New York

1 2
apartment , Sleepy Hollow
This 4-bedroom home is located in Tarrytown, just a short drive from Sleepy Hollow and its famous landmarks. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The home comfortably sleeps up to 8 guests and has two full bathrooms. Guests can enjoy free parking, high-speed internet, a fully equipped kitchen, and access to four bicycles for exploring the surrounding area.

Best Sleepy Hollow, NY vacation rentals with parking

Upscale Downtown 2br | Lux Amenities | Laundry - Sleepy Hollow, NY
8.6 4 reviews
Sleepy Hollow, NY
08/08 – 08/13
$454/nightTotal: $2270 (5 )

Upscale Downtown 2br | Lux Amenities | Laundry

2 2
apartment , White Plains
This White Plains apartment is located in the city center, just a short walk from the Cudner-Hyatt House Complex, Capitol Theatre, Westchester Skating Academy, and Legoland Discovery Center Westchester. A short train ride connects you to Manhattan, making it easy to explore the city.
The 1000-square-foot apartment comfortably accommodates up to 5 guests with 2 bedrooms and 2 bathrooms. Amenities include a fitness center, rooftop sky lounge, outdoor pool, children's playroom, business center, game room, and a dog wash.
Prime Luxe 3-br Nyc - Free Parking - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$1110/nightTotal: $7770 (7 )

Prime Luxe 3-br Nyc - Free Parking

1 2
apartment , White Plains
This pet-friendly apartment in White Plains is located in a residential district, offering convenient access to White Plains Hospital Center, Central Park, and the Metropolitan Museum of Art.
This accommodation for 2 guests includes a microwave oven, dishwasher, air conditioning, and parking, with on-site laundry facilities available.
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.
Cozy Apartment To Relax - Apartment "A" - Sleepy Hollow, NY
Sleepy Hollow, NY
06/27 – 07/04
$247/nightTotal: $1729 (7 )

Cozy Apartment To Relax - Apartment "A"

2 2
apartment , Yonkers
This Yonkers rental unit in Getty Square offers convenient access to local attractions, being a 3-minute drive from Untermyer Gardens Conservancy and a 5-minute drive from Van Cortlandt Park.
This apartment features a private terrace with outdoor furniture, complimentary Wi-Fi, a fully equipped kitchen, and air conditioning, with proximity to Westchester County Center and attractions in New York City.

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
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.
3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
8.0 4 reviews
Sleepy Hollow, NY
09/30 – 10/07
$683/nightTotal: $4781 (7 )

3 Mi To Downtown: Spacious White Plains Home

5 2
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.
Piermont Oasis - Sleepy Hollow, NY
9.8 18 reviews
Sleepy Hollow, NY
08/08 – 08/13
$199/nightTotal: $995 (5 )

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
9.2 15 reviews
Sleepy Hollow, NY
09/30 – 10/07
$642/nightTotal: $4494 (7 )

3 Mi To Downtown: Spacious White Plains Home

5 2
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.

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.

Spacious Luxury Retreat Sleeps 16  Prime Area  Free Parking  Near Nyc - Sleepy Hollow, NY
Sleepy Hollow, NY
10/23 – 10/26
$1371/nightTotal: $4113 (3 )

Spacious Luxury Retreat Sleeps 16 Prime Area Free Parking Near Nyc

3 6
apartment , White Plains
This 3-bedroom, 2-bathroom apartment in White Plains accommodates up to 16 guests and is located near The Westchester Mall and Rockefeller State Park Preserve.
This spacious rental offers a fully equipped kitchen, comfortable seating for group gatherings, and is conveniently situated for exploring local attractions.
The Cozy Den - Sleepy Hollow, NY
9.4 72 reviews
Sleepy Hollow, NY
09/30 – 10/07
$192/nightTotal: $1344 (7 )

The Cozy Den

1 2
apartment , Nyack
This cozy den is located in a quiet and safe neighborhood in Nyack, just a short walk from the town center and offering beautiful views of the Hudson River. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a private entrance, a modern kitchen with a fridge and microwave, air conditioning, a garden, parking, internet access, and is pet-friendly.
Convenient Apt: 2 Mi To Sprain Ridge Park! - Sleepy Hollow, NY
Sleepy Hollow, NY
08/08 – 08/13
$1432/nightTotal: $7160 (5 )

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.
A Comfortable Cozy Place In The Heart Of Nyack - Sleepy Hollow, NY
Sleepy Hollow, NY
08/17 – 08/27
$266/nightTotal: $2660 (10 )

A Comfortable Cozy Place In The Heart Of Nyack

1 3
apartment , Nyack
This Nyack condo offers a prime central location, placing you within a well-established residential area with convenient access to the town's shops, restaurants, and cultural venues.
This pet-friendly rental accommodates two guests with a private bedroom and bathroom, featuring air conditioning, internet, and a kitchen, and you'll likely have the entire residence to yourself, allowing you to experience Nyack like a local.
©2026 cozycozy.com