12 Holiday Rentals and Airbnb in Sleepy Hollow, NY
10 9 reviews
Sleepy Hollow, NY
27/06 – 04/07
NZ$1556/nighttotal: NZ$10892 (7 )
Stone Kiln Castle
4 2
apartment , Pleasantville
Stone Kiln Castle, a former tea house and speakeasy dating back to 1920, is situated in Pleasantville, New York, within walking distance of restaurants, shops, and the train station, and less than a kilometre from Graham Hills Park and Rockefeller State Park. This four-bedroom, three-bathroom property sleeps eight guests and boasts a chef's kitchen with double oven and six-burner stove, a wood-burning fireplace, a private screening room with a queen-sized bed, and is close to the Jacob Burns Film Center.
9.3 20 reviews
Sleepy Hollow, NY
30/09 – 07/10
NZ$930/nighttotal: NZ$6510 (7 )
Poolhouse Paradise On Private Grounds Close To Nyc
2 2
bungalow , Briarcliff Manor
This charming bungalow is located just a short drive from Briarcliff Manor's town centre, offering easy access to local shops, restaurants and attractions. It has consistently received excellent ratings for its cleanliness, location and guest experience. The cottage features two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy a range of amenities including a private pool and hot tub, a fully equipped kitchen, a spacious living area and a beautiful garden.
10 2 reviews
Sleepy Hollow, NY
23/10 – 26/10
NZ$7131/nighttotal: NZ$21393 (3 )
Shadowbrook Manor - 1890's Gem
1 6
apartment , Tarrytown
Shadowbrook Manor is a classic English Country Manor located in Tarrytown, just a short walk from nearby hotels and the charming village centre. This property has consistently received excellent ratings for its cleanliness, location, and overall experience. The manor has five bedrooms and one bathroom, comfortably accommodating up to 16 guests. It offers a fully equipped kitchen, parking, and internet access, making it ideal for both short and long stays.
Sleepy Hollow, NY
30/09 – 07/10
NZ$241/nighttotal: NZ$1687 (7 )
Piermont Haven
1 2
apartment , Piermont
This flat in Piermont offers easy access to the town's shops and restaurants, all within a 500-meter walk. This compact accommodation for two includes a kitchen with a fridge and microwave, air conditioning, and Wi-Fi, ideal for short stays.
9.2 31 reviews
Sleepy Hollow, NY
23/10 – 26/10
NZ$2396/nighttotal: NZ$7188 (3 )
Westchester Summer: Pool Pet Friendly Events Games
1 6
house , Ossining
This 6000 sq ft estate in Ossining, New York, is situated just 8 kilometres from White Plains and 49 minutes by train to New York City, offering convenient access to Rockefeller State Park Preserve (800 metres away), Croton Gorge Park (6.4 kilometres away), and Sleepy Hollow (16 kilometres away). This family-friendly, pet-welcoming property accommodates up to 13 guests with 5 bedrooms and 4 bathrooms, featuring a custom bar, pool table, arcade games, a seasonal swimming pool, fully equipped kitchen, fast WiFi, and private parking for 5 vehicles.
9.8 8 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$351/nighttotal: NZ$1755 (5 )
Cozy Studio With Reading Nook
1 2
studio , White Plains
This one-bedroom flat is conveniently located in White Plains, just 1.5 kilometres from the Westchester County Center and a 20-minute walk from the Galleria at White Plains shopping centre. The area is well-connected, offering easy access to local amenities and attractions. The flat can accommodate up to 3 guests and has a fully equipped kitchen, a comfortable living area with a smart TV, and a bathroom. Enjoy modern amenities such as air conditioning, heating, and Wi-Fi, along with access to a spa, parking, and a lakefront location perfect for water activities.
9.0 22 reviews
Sleepy Hollow, NY
17/08 – 27/08
NZ$341/nighttotal: NZ$3410 (10 )
Cozy Congers Studio With Kitchen
1 3
apartment , Congers
This Congers, New York studio flat is conveniently located near Rockland Lake State Park and Congers Lake, offering easy access to the Metro-North Railroad and major airports within 80-80 km. The newly remodelled, fully furnished suite features a queen-size bed, sofa bed, full kitchen with oven, microwave and coffee machine, private porch, and on-site parking; accommodating up to three guests and close to walking trails and various outdoor activities.
Sleepy Hollow, NY
23/10 – 26/10
NZ$2359/nighttotal: NZ$7077 (3 )
Elegant Spacious Retreat Sleeps 16 Prime Area Free Parking Near Nyc
3 6
apartment , Valhalla
This luxury 3-bedroom flat in White Plains is situated approximately 3.2 kilometres from Valhalla, providing convenient access to local landmarks such as the Jacob Purdy House and the Rockefeller Archive Centre. This accommodation can host up to 16 guests, featuring four queen beds, a fully equipped gourmet kitchen, and is ideally located for visiting attractions like the Westchester County Center, which is just 1.6 kilometres away.
9.8 18 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$343/nighttotal: NZ$1715 (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.
8.0 2 reviews
Sleepy Hollow, NY
27/06 – 04/07
NZ$456/nighttotal: NZ$3192 (7 )
Polished 1br W/ Accessible Room Features + Sauna
1 2
apartment , Ossining
This accessible studio apartment in Ossining, NY, provides a peaceful Hudson Valley retreat just a short distance from New York City, with proximity to historical sites such as Van Cortlandt Manor. This studio offers a queen guestroom with an ADA-friendly roll-in shower, accommodating up to two guests with amenities including Wi-Fi, air conditioning, a fitness centre, sauna, and on-site dining options like Café 56.
Sleepy Hollow, NY
30/09 – 07/10
NZ$479/nighttotal: NZ$3353 (7 )
Ardsley Abode
1 2
apartment , Ardsley
This 1920s Colonial residence is situated centrally within Ardsley Village, offering direct access to local shops and eateries. This two-bedroom flat accommodates up to six guests and features a kitchen, air conditioning, and a Jacuzzi, perfect for a comfortable stay with modern updates and a vintage-chic aesthetic.
Sleepy Hollow, NY
08/08 – 13/08
NZ$472/nighttotal: NZ$2360 (5 )
Cozy Apartment To Relax - Apartment "A"
2 2
apartment , Yonkers
This flat offers a prime Yonkers location, just 3 minutes by car from Untermyer Gardens Conservancy and 5 minutes from Van Cortlandt Park, with convenient access to the Westchester County Center and the Metropolitan Museum of Art. This property provides complimentary Wi-Fi, air conditioning, a fully equipped kitchen with a fridge and microwave, and a private terrace, making it ideal for exploring attractions like the Bronx Zoo and Yankee Stadium.
Best family friendly Sleepy Hollow, NY holiday rentals
Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best family friendly rentals
Sleepy Hollow, NY
08/08 – 13/08
NZ$1190/nighttotal: NZ$5950 (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.
Sleepy Hollow, NY
23/10 – 26/10
NZ$2636/nighttotal: NZ$7908 (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.
8.0 238 reviews
Sleepy Hollow, NY
27/06 – 04/07
NZ$542/nighttotal: NZ$3794 (7 )
Global Luxury Suites Downtown White Plains
1 2
apartment , White Plains
This apartment is conveniently located in downtown White Plains, just a short distance from Manhattanville College and SUNY Purchase. Guests have praised its excellent location, cleanliness, and overall value. The apartment features a comfortable living space with a well-equipped kitchen and modern amenities. Guests can enjoy access to a swimming pool, fitness centre, and other on-site facilities, making it a great choice for travellers seeking a convenient and comfortable stay in White Plains.
9.8 18 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$420/nighttotal: NZ$2100 (5 )
Cozy Secret Apartment With Free Parking In Yonkers
1 2
apartment , Yonkers
This family-friendly apartment in Northwest Yonkers is situated within 3.2km of Untermyer Gardens and the Hudson River, and within 4.8km of Legoland Discovery Centre Westchester and the Hudson River Museum. This 37 square metre flat offers one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, free Wi-Fi, a terrace, and on-site parking.
Best Sleepy Hollow, NY holiday rentals with parking
9.7 20 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$2220/nighttotal: NZ$11100 (5 )
Hudson River Views: Briarcliff Manor Home W/ Deck
4 2
apartment , Briarcliff Manor
This Briarcliff Manor holiday home provides extensive views of the Hudson River and Palisades, situated a short drive from Historic Sleepy Hollow and Rockefeller State Park Preserve. This spacious 385 square meter residence accommodates up to 12 guests with four bedrooms and six bathrooms, featuring a well-appointed games room, outdoor entertaining areas with a pizza oven, multiple fireplaces, and eight dedicated home office spaces, plus an EV charger.
9.2 29 reviews
Sleepy Hollow, NY
17/08 – 27/08
NZ$849/nighttotal: NZ$8490 (10 )
3 Mi To Downtown: Spacious White Plains Home
5 3
apartment , Fairview
This five-bedroom house in White Plains, New York, offers easy access to New York City via a short train journey and is within walking distance of Westchester County's largest walkable downtown area. Sleeping thirteen guests comfortably, this three-storey property boasts a well-equipped kitchen, Smart TVs, free WiFi, a private patio and garden, and garage parking for up to four vehicles.
9.8 18 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$611/nighttotal: NZ$3055 (5 )
Stylish Tarrytown Studio - Walk To Train & Main St
1 2
studio , Tarrytown
This Tarrytown apartment is conveniently located less than 1.6km from Tarrytown Music Hall and Pierson Park, and under 1.6km from Philipsburg Manor and the Old Dutch Church of Sleepy Hollow. The self-catering flat sleeps four, boasting a fully equipped kitchen, a jacuzzi, garden, parking, and a terrace, all within a smoke-free environment.
Sleepy Hollow, NY
27/06 – 04/07
NZ$465/nighttotal: NZ$3255 (7 )
1br Queen Near Nyc | Trails, Biking & Sauna Bliss
1 2
apartment , Ossining
This aparthotel in Ossining offers a convenient base for exploring Croton-on-Hudson, situated a short distance from Mohansic Golf Course, Captain Lawrence Brewing, Bear Mountain State Park, and the Old Croton Aqueduct State Park. Guests can enjoy complimentary high-speed Wi-Fi, air-conditioned rooms, and an on-site sauna, with easy access to outdoor pursuits such as hiking and biking.
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 folklore. You can't miss the iconic Sleepy Hollow Cemetery, where Washington Irving is buried. Then there's the Old Dutch Church, made famous in Irving's 'The Legend of Sleepy Hollow'. And just a short drive away is Lyndhurst Mansion, a beautiful 19th-century Gothic Revival mansion.
What are the best Airbnb and holiday rentals in Sleepy Hollow, NY?
Which walking or cycling routes are the best in Sleepy Hollow, NY?
The Old Croton Aqueduct Trail is a fantastic option for both walking and cycling. It follows the historic aqueduct and offers beautiful views of the Hudson River. There's also the scenic Sleepy Hollow Riverwalk, which runs along the Pocantico River.
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 spot for outdoor activities. You can play golf at the Sleepy Hollow Country Club, go for a hike in the Rockefeller State Park Preserve, or enjoy a leisurely paddle in the Hudson River. The area is also popular for birdwatching, especially in the fall.
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 several other towns and cities. You can easily reach Tarrytown, with its charming shops and restaurants, or head to the bustling city of Yonkers, just a short drive away. And of course, you're just a hop, skip, and jump from New York City.
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 typically offer a range of amenities to make your stay comfortable. You can expect to find kitchens, laundry facilities, and often outdoor spaces like patios or decks. Many rentals also have Wi-Fi and cable TV.
What time of year is best to rent a vacation rental Sleepy Hollow, NY?
Sleepy Hollow is lovely year-round, but the best time to visit depends on your preferences. Autumn is spectacular with the fall foliage, while spring offers milder temperatures and blooming flowers. Summer is great for outdoor activities, and winter brings a touch of magic with the holiday season.
What are the local dishes in Sleepy Hollow, NY region?
The Hudson Valley is known for its farm-to-table cuisine. You'll find plenty of fresh, seasonal dishes featuring local ingredients. Try the Hudson Valley apple pie, a classic regional treat. And don't miss the chance to sample some local craft beers.
Destinations nearby
Best Sleepy Hollow, NY holiday rentals with a balcony
9.2 15 reviews
Sleepy Hollow, NY
17/08 – 27/08
NZ$895/nighttotal: NZ$8950 (10 )
3 Mi To Downtown: Spacious White Plains Home
5 3
apartment , Fairview
This Fairview property, a seven-bedroom, three-bathroom house, is situated 4.8 kilometres from White Plains city centre, 3.2 kilometres from the Bronx River Greenway, and offers easy access to New York City (51.5 kilometres away). The 298 square metre dwelling boasts a spacious layout sleeping up to twelve guests, featuring a private patio, garden with gas grill, garage parking for four vehicles, plus Smart TVs, a washer/dryer, and complimentary toiletries.
8.0 4 reviews
Sleepy Hollow, NY
30/09 – 07/10
NZ$1175/nighttotal: NZ$8225 (7 )
3 Mi To Downtown Spacious White Plains Home
5 2
house , Fairview
This spacious five-bedroom house in White Plains, Fairview, is situated 5km from White Plains city centre, offering easy access to Manhattanville College (9km), SUNY Purchase (11km), Iona College (18km), and Westchester County Airport (10km). The 298 square metre property boasts three bathrooms, a fully equipped kitchen including a dishwasher and microwave, private parking, a terrace, garden, free Wi-Fi, and comfortably accommodates up to 25 guests.
Sleepy Hollow, NY
27/06 – 04/07
NZ$635/nighttotal: NZ$4445 (7 )
Beautiful Apartment 1 In Great Pleasantville, Ny
3 2
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
NZ$2786/nighttotal: NZ$13930 (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.
Best pet friendly Sleepy Hollow, NY holiday rentals
Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best pet friendly rentals
8.6 4 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$781/nighttotal: NZ$3905 (5 )
Upscale Downtown 2br | Lux Amenities | Laundry
2 2
apartment , White Plains
This apartment is conveniently located in the city centre of White Plains, close to the train station and a short drive from the Hudson River, making it an ideal base for exploring both the city and surrounding countryside. The apartment is ideal for families or groups, offering 2 bedrooms and 2 bathrooms with a floor area of 93 square metres and a guest capacity of 5. The apartment is well-equipped with modern amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a garden and parking. There is also a concierge service, high-speed internet, laundry facilities and a range of activities to enjoy, such as a fitness centre, a game room and a children's playroom.
Sleepy Hollow, NY
08/08 – 13/08
NZ$2462/nighttotal: NZ$12310 (5 )
Convenient Apt 2 Mi To Sprain Ridge Park!
1 2
apartment , Yonkers
This one-bedroom flat is conveniently located in Yonkers, just 3 kilometres from Sprain Ridge Park, 16 kilometres from the Bronx Zoo and 19 kilometres from Manhattanville College. The surrounding area offers easy access to major highways and public transport, making it a great base for exploring the region. The 65 square metre flat comfortably sleeps up to three guests and features a fully equipped kitchen, a private entrance, air conditioning, free Wi-Fi and parking. Enjoy the convenience of having a fridge, a microwave oven, towels and bed linen provided, as well as the added bonus of being pet-friendly.
Sleepy Hollow, NY
08/08 – 13/08
NZ$2297/nighttotal: NZ$11485 (5 )
Stylish 3br Home Game Room Free Parking Sleeps 16
3 2
apartment , White Plains
This three-bedroom, two-bathroom flat in White Plains, conveniently situated within 2 kilometres of cultural sites such as the Westchester Broadway Theatre and Rockefeller Archive Center, offers ample space for up to 16 guests. This White Plains rental, ideal for large groups and families, features five queen beds, a dedicated game room, free on-site parking, and a fully equipped kitchen, ensuring a comfortable and entertaining stay for all.
9.8 14 reviews
Sleepy Hollow, NY
08/08 – 13/08
NZ$2932/nighttotal: NZ$14660 (5 )
Hudson River Views: Briarcliff Manor Home W/ Deck
4 2
apartment , Briarcliff Manor
This spacious apartment is located in Briarcliff Manor, just a short distance from the Sleepy Hollow Country Club and Rockefeller State Park Preserve, offering a tranquil setting for your stay. It has received excellent user ratings, indicating a high level of satisfaction from previous guests. This three-bedroom, four-bathroom apartment spans 386 square metres and can accommodate up to 10 guests, providing ample space for families or groups. The apartment offers a range of amenities, including a game room, home office, gym, and a spacious deck with stunning views of the Hudson River and Palisades Mountains.