Best Holiday rentals and Airbnb offers in Sleepy Hollow, NY
9.8 175 reviews
Sleepy Hollow, NY
27/06 – 04/07
£211/nighttotal: £1477 (7 )
Hudson River Forest Marsh Cozy Winter Wonderland
1 2
apartment , Piermont
This charming studio apartment is situated in Piermont, a picturesque village on the Hudson River, just 15 miles from Manhattan and 11 miles from the George Washington Bridge. The property has received excellent ratings for its location, cleanliness, and overall experience. The studio is perfect for a couple or a small group of three, offering a comfortable and well-equipped space. The apartment features a full kitchen with a dishwasher, a washer and dryer, a recording studio, a garden, and access to three bikes, allowing guests to explore the surrounding area.
10 7 reviews
Sleepy Hollow, NY
23/10 – 26/10
£1844/nighttotal: £5532 (3 )
Clean And Large Family Home In Nyc Suburbs
5 6
apartment , Scarsdale
This spacious apartment is located in Scarsdale, a short walk from the Metro North train station, offering a 45-minute ride to Grand Central Station in NYC. It benefits from excellent user, location and cleanliness ratings. The property is ideal for families or groups of up to 10 guests, and features a private garden, a fully equipped kitchen, laundry facilities and ample storage space. Guests can enjoy a relaxing outdoor space and benefit from a peaceful, residential setting with easy access to shops, restaurants and amenities in Scarsdale Village.
10 7 reviews
Sleepy Hollow, NY
17/08 – 27/08
£196/nighttotal: £1960 (10 )
Palisade Suite -Cozy 1-bdr Dobbs Ferry-30 Min From Nyc- Ac & Hudson River Views
1 3
apartment , Dobbs Ferry
This Dobbs Ferry apartment is situated near the Hudson River, approximately 34km from the Bronx Zoo and 18km from the Westchester County Center. The one-bedroom, one-bathroom flat sleeps four guests and offers amenities including Wi-Fi, on-site parking, and a fully equipped kitchen; nearby attractions include the Untermyer Gardens Conservancy and the Hudson River Museum.
Sleepy Hollow, NY
30/09 – 07/10
£187/nighttotal: £1309 (7 )
Updated Victorian In The Heart Of Nyack
3 2
apartment , Nyack
This Victorian property in Nyack offers spectacular Hudson River views from a peaceful, tree-lined street, providing convenient access to local amenities and a 10-minute walk to the shuttle stop for easy travel. This 3-bedroom, 2-bathroom apartment accommodates up to 6 guests and features a private backyard courtyard, balcony terrace, WiFi, and central air conditioning, making it ideal for those seeking a comfortable stay with modern conveniences.
9.8 245 reviews
Sleepy Hollow, NY
17/08 – 27/08
£112/nighttotal: £1120 (10 )
Private Charming Studio Efficiency
1 3
apartment , Dobbs Ferry
This studio apartment is located in Dobbs Ferry, just a short walk from restaurants like Sushi Mike's and The Parlor, making it easy to explore the local culinary scene. The apartment has received excellent ratings for cleanliness, location, and user experience, ensuring a comfortable stay. The basement apartment offers a private entrance and is ideal for solo travellers, couples, or business travellers. Guests can enjoy a fully equipped kitchen with a fridge, microwave, coffee pot, and toaster oven, as well as easy access to public transportation for exploring Dobbs Ferry and New York City.
Sleepy Hollow, NY
23/10 – 26/10
£667/nighttotal: £2001 (3 )
Modern City Studio In Heart Of White Plains, 2 Units
2 6
studio , White Plains
This modern White Plains city apartment is centrally located near the Westchester County Center. The 63-square-metre (678 square-foot) self-catering apartment sleeps eight, offering two bedrooms, two bathrooms, free Wi-Fi, air conditioning, and access to a hotel swimming pool and fitness centre.
10 14 reviews
Sleepy Hollow, NY
08/08 – 13/08
£110/nighttotal: £550 (5 )
A Gem In Piermont.
1 2
apartment , Piermont
This Piermont studio apartment offers a private and secluded setting with wooded views, conveniently located within walking distance of Piermont village, its pier, and Tallman State Park. The self-catering unit, sleeping up to two guests, features a kitchen with a fridge and microwave, air conditioning, a private balcony, and a garden; access is via private stairs above the garage.
9.9 20 reviews
Sleepy Hollow, NY
17/08 – 27/08
£395/nighttotal: £3950 (10 )
Stylish, Cozy 2 Br Pied-á-terre
1 3
apartment , Tarrytown
This Tarrytown apartment is situated near the Old Croton Aqueduct Trail, a short walk from Tarrytown's Main Street shops and cafes, and approximately 1 km from the Metro-North Train Station and the Hudson River Walk. The self-catering flat offers two bedrooms, sleeping up to four guests, and includes a fully equipped kitchen with dishwasher, a 65" smart TV, in-unit laundry, and a private entrance.
9.9 66 reviews
Sleepy Hollow, NY
08/08 – 13/08
£182/nighttotal: £910 (5 )
Idyllic & Chic In Piermont, 20 Min From Gw Bridge
2 2
apartment , Piermont
This Piermont holiday home enjoys a prime village location, a short 0.8 km stroll from the Hudson River and Tallman Park, and is within 3.2 km of the George Washington Bridge. The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen, living room with TV, in-unit laundry, and outdoor space; amenities include Wi-Fi, cable TV, and access to streaming services such as Netflix, Amazon Prime Video, and HBO Max.
10 5 reviews
Sleepy Hollow, NY
27/06 – 04/07
£1539/nighttotal: £10773 (7 )
Classic Tudor In A Prime Nyc Suburban Location.
4 2
apartment , Scarsdale
This Scarsdale house, a mile (1.6km) from Scarsdale Metro-North station for easy Manhattan access, offers convenient proximity to top-rated schools and town amenities. The spacious four-bedroom property sleeps nine, boasting a finished basement with kitchenette and large TV, a private backyard, two driveways, and access to Scarsdale's town pool and tennis courts (membership fees apply for stays over 30 days).
Sleepy Hollow, NY
27/06 – 04/07
£905/nighttotal: £6335 (7 )
2br House W/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
2 2
apartment , Yonkers
This two-bedroom flat in Yonkers' Bryn Mawr district offers a peaceful residential setting, conveniently located within 8 kilometres of the Solomon R. Guggenheim Museum and the Bronx Zoo, and approximately 10 kilometres from Legoland Discovery Center Westchester. This property accommodates up to 10 guests with two queen beds, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, complimentary on-site parking, and is pet-friendly, providing a comfortable private home experience close to transport, dining, and shops.
8.0 2 reviews
Sleepy Hollow, NY
30/09 – 07/10
£206/nighttotal: £1442 (7 )
Private Suite
1 2
chalet , Greenville
This Scarsdale lodge is conveniently situated for exploring Pelham Bay Park (27 kilometres) and Van Cortlandt Park (22 kilometres), with the Bronx Zoo and Westchester County Centre also readily accessible. This chalet offers home comforts including Wi-Fi and air conditioning, with essential toiletries and an ironing board provided for your convenience.
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.
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.
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.
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.
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.
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.
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.
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.
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?
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.
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.
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.
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.
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.
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.
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.
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.
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.