Holiday Rentals in Sleepy Hollow, NY

12 available vacation rental offers

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Sleepy Hollow, NY holiday rentals
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Best Holiday rentals and Airbnb offers in Sleepy Hollow, NY

Explore Holiday Rentals for Families in Sleepy Hollow, NY

Getting the holiday rental right makes all the difference for a family trip to Sleepy Hollow, NY. Find city attractions within easy reach. Start comparing now.

Pureheart House, Spacious, 3bdr 30 Mn From Manhattan. Nyc - Sleepy Hollow, NY
8.8 52 reviews
Sleepy Hollow, NY
23/10 – 26/10
£259/nighttotal: £777 (3 )

Pureheart House, Spacious, 3bdr 30 Mn From Manhattan. Nyc

3 6
apartment , Yonkers
This charming house is located in Northeast Yonkers, a short distance from the Hudson River Museum and Westchester County Center. The property has received excellent user ratings, making it a popular choice for travellers.
The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. You’ll find a fully equipped kitchen, a spacious living room with a 65" TV, a dedicated workspace, a terrace, a garden, a spa and parking on site.
World Cup Base: 22m To Metlife - Sleepy Hollow, NY
10 6 reviews
Sleepy Hollow, NY
27/06 – 04/07
£555/nighttotal: £3885 (7 )

World Cup Base: 22m To Metlife

1 2
apartment , Piermont
This charming house is situated just 20 miles north of New York City, offering stunning views of the Hudson River and a peaceful escape from the city's hustle and bustle. The surrounding area is perfect for exploring scenic hiking trails and discovering the quaint charm of nearby riverfront towns.
The house has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. It features modern amenities, including a fully equipped kitchen, air conditioning, and a garden, ensuring a comfortable and enjoyable stay.
Spacious 3br Home / Free Parking / Perfect For Families & Groups - Sleepy Hollow, NY
Sleepy Hollow, NY
08/08 – 13/08
£613/nighttotal: £3065 (5 )

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

3 2
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.
Close To New York City With Bridge View & Parking - Sleepy Hollow, NY
9.6 170 reviews
Sleepy Hollow, NY
08/08 – 13/08
£422/nighttotal: £2110 (5 )

Close To New York City With Bridge View & Parking

1 2
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.

Choose the Right Self-Catering Holiday Rentals with Free Parking in Sleepy Hollow, NY

Driving to Sleepy Hollow, NY? Your holiday rental includes a car park, making the city centre simple to navigate from arrival.

Garden Loft With Patios & Green Space · Westchester Retreat - Sleepy Hollow, NY
9.2 5 reviews
Sleepy Hollow, NY
08/08 – 13/08
£203/nighttotal: £1015 (5 )

Garden Loft With Patios & Green Space · Westchester Retreat

1 2
apartment , Ardsley
This Ardsley apartment is situated in Scarsdale, a 7-minute drive (approximately 4.5 km) from the Westchester County Center and a 21-minute drive (approximately 13.5 km) from the Bronx Zoo.
This 62-square-metre flat offers one bedroom, one bathroom, sleeps four guests, and includes amenities such as on-site parking, Wi-Fi, air conditioning, and a fully equipped kitchen with microwave, oven and stove, plus a garden and in-unit laundry facilities.
Spacious Yonkers Home Sleeps 16  Game Room  Gazebo  Perfect For Groups - Sleepy Hollow, NY
Sleepy Hollow, NY
27/06 – 04/07
£1167/nighttotal: £8169 (7 )

Spacious Yonkers Home Sleeps 16 Game Room Gazebo Perfect For Groups

3 2
apartment , Yonkers
This three-bedroom residence is situated in Yonkers' Bryn Mawr district, offering a swift commute to New York City and convenient access to local amenities, with the city centre approximately 24 kilometres away.
This property accommodates up to 16 guests, featuring a fully equipped kitchen, a dedicated game room, a private gazebo with outdoor space, and fast WiFi, making it ideal for large family gatherings or group holidays.
Near Metronorth Station 2 Br | Kitchen + W/d - Sleepy Hollow, NY
8.4 16 reviews
Sleepy Hollow, NY
08/08 – 13/08
£338/nighttotal: £1690 (5 )

Near Metronorth Station 2 Br | Kitchen + W/d

2 2
apartment , White Plains
This White Plains apartment is ideally situated near the Galleria Mall, White Plains Hospital, and Westchester County Centre, all within a 2.4km radius, offering easy access to the Metro-North station for a quick commute to New York City.
The 93 square metre flat features three bedrooms, two bathrooms, and sleeps five guests comfortably, boasting a fully equipped kitchen, fitness centre access, swimming pool, and concierge service.
Convenient Apt: 2 Mi To Sprain Ridge Park! - Sleepy Hollow, NY
Sleepy Hollow, NY
27/06 – 04/07
£1117/nighttotal: £7819 (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.

Frequently asked questions about holiday rentals in Sleepy Hollow, NY

  • What are some interesting places to visit in or near Sleepy Hollow, NY?

    Sleepy Hollow is steeped in history and charm. You can't miss the iconic Sleepy Hollow Cemetery, where Washington Irving, the author of 'The Legend of Sleepy Hollow', is buried. Also, visit the Old Dutch Church, which inspired Irving's story. For a taste of local history, head to Philipsburg Manor, a restored 18th-century estate that showcases colonial life.
  • What are the best Airbnb and holiday rentals in Sleepy Hollow, NY?

  • Which walking or cycling routes are the best in Sleepy Hollow, NY?

    For a scenic walk, try the Old Croton Aqueduct Trail, a 40km trail that winds through the countryside. The Sleepy Hollow Walkway is great for a leisurely stroll along the Hudson River. If you're looking for a cycle, the 10km paved bike path along the Old Croton Aqueduct Trail is a popular choice.
  • 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. The Hudson River is a great spot for kayaking or canoeing. You can also go hiking at the Rockefeller State Park Preserve, which has over 1600 hectares of trails. For a more leisurely activity, try playing a round of golf at the Sleepy Hollow Country Club.
  • What are the best holiday rentals with a pool in Sleepy Hollow, NY?

    The best holiday 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 interesting towns. You can easily reach Tarrytown, with its charming shops and restaurants, just a short drive away. A little further afield, you can visit the vibrant city of New York, just a 40-minute train ride from the Tarrytown station.
  • 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 offer a variety of amenities. Many rentals include a kitchen, allowing you to cook your own meals. You'll often find comfortable living spaces, bedrooms, and bathrooms. Some rentals also offer extras like laundry facilities, Wi-Fi, and outdoor spaces like patios or gardens.
  • What time of year is best to rent a vacation rental Sleepy Hollow, NY?

    Sleepy Hollow is beautiful year-round, but the best time to visit depends on your preferences. Spring and autumn offer mild weather and stunning foliage. Summer is warm and sunny, perfect for outdoor activities. Winter brings a charming, snowy atmosphere, ideal for cozying up by the fireplace.
  • What are the local dishes in Sleepy Hollow, NY region?

    Sleepy Hollow is in the Hudson Valley, known for its fresh produce and farm-to-table cuisine. You'll find plenty of restaurants serving classic American dishes with a modern twist. Try the local apple pie, made with apples from the region's orchards. You can also find delicious seafood, thanks to the nearby Hudson River.

Destinations nearby

Best Self-Catering Holiday Rentals with a Terrace in Sleepy Hollow, NY

Enjoying morning coffee with city skyline views is a simple pleasure when staying in these holiday rentals and Airbnbs in Sleepy Hollow, NY.

557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests - Sleepy Hollow, NY
Sleepy Hollow, NY
23/10 – 26/10
£1144/nighttotal: £3432 (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.
Piermont Oasis - Sleepy Hollow, NY
9.8 18 reviews
Sleepy Hollow, NY
08/08 – 13/08
£149/nighttotal: £745 (5 )

Piermont Oasis

1 2
apartment , Piermont
This Piermont apartment, near Tallman Mountain State Park and Palisades Interstate Park, offers easy access to Piermont's natural beauty and cultural attractions such as the Tarrytown Music Hall (a short drive away).
The self-catering flat features a private balcony overlooking mountain greenery, one bedroom, one bathroom, sleeps two guests, and includes WiFi, a kitchenette, and parking.
Beautiful Apartment 1 In Great Pleasantville, Ny - Sleepy Hollow, NY
Sleepy Hollow, NY
17/08 – 27/08
£334/nighttotal: £3340 (10 )

Beautiful Apartment 1 In Great Pleasantville, Ny

3 3
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.
Hudson River Views Briarcliff Manor Home With Deck - Sleepy Hollow, NY
10 2 reviews
Sleepy Hollow, NY
08/08 – 13/08
£1209/nighttotal: £6045 (5 )

Hudson River Views Briarcliff Manor Home With Deck

4 2
house , Briarcliff Manor
This Briarcliff Manor estate is situated just 11 miles from The Palisades Center Mall and 14 miles from Manhattanville College, offering stunning Hudson River views and a peaceful setting. The property has received excellent ratings for user experience, location, and cleanliness.
The 3-bedroom home provides ample space for families or groups, with a floor area of 386 square metres and a guest capacity of 10. Enjoy modern amenities such as free Wi-Fi, cable TV, a washing machine, a fully equipped kitchen, a spa, a fitness centre, and a garden.

Popular Pet-Friendly Holiday Rentals in Sleepy Hollow, NY

Bringing your dog to Sleepy Hollow, NY? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.

Castle Retreat W/ Pool, Bbq, Game Room & Pets Ok! - Sleepy Hollow, NY
9.2 7 reviews
Sleepy Hollow, NY
23/10 – 26/10
£1224/nighttotal: £3672 (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.
Charming 3br Home - Quiet Stay, Close To Nyc - Sleepy Hollow, NY
9.9 127 reviews
Sleepy Hollow, NY
23/10 – 26/10
£324/nighttotal: £972 (3 )

Charming 3br Home - Quiet Stay, Close To Nyc

1 6
house , White Plains
This three-bedroom townhouse is situated in White Plains, a short 2-kilometre walk from North White Plains station, providing easy access to Manhattan and close proximity to the Westchester Mall, Target and Whole Foods. The property offers a full kitchen, a dining room, a laundry facility, a dedicated office space and parking for multiple cars.
Five Bedroom Family Home In Larchmont - Guest Suite And Large Yard - Sleepy Hollow, NY
Sleepy Hollow, NY
08/08 – 13/08
£516/nighttotal: £2580 (5 )

Five Bedroom Family Home In Larchmont - Guest Suite And Large Yard

5 2
apartment , New Rochelle
This Larchmont holiday home, situated within 5km of Iona College and Harbor Island Park and 10km of Monroe College and Hudson Park and Beach, offers convenient access to New Rochelle's key attractions.
This spacious 233 square metre property sleeps up to 10 guests, boasting 4 bedrooms, 2 bathrooms, a fully equipped kitchen, fitness centre, garden, terrace, parking, and free Wi-Fi.
Nyack- Private Studio Steps From Downtown - Sleepy Hollow, NY
9.4 10 reviews
Sleepy Hollow, NY
30/09 – 07/10
£155/nighttotal: £1085 (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.
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