Holiday Rentals in Sleepy Hollow, NY

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Sleepy Hollow, NY holiday rentals
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12 Holiday Rentals and Airbnb in Sleepy Hollow, NY

Best family friendly Sleepy Hollow, NY holiday rentals

Among the 9 accommodations in Sleepy Hollow, NY, here are the 4 best family friendly rentals

Five Bedroom Family Home In Larchmont - Guest Suite And Large Yard - Sleepy Hollow, NY
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.
557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests - Sleepy Hollow, NY
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.
Global Luxury Suites Downtown White Plains - Sleepy Hollow, NY
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.
Cozy Secret Apartment With Free Parking In Yonkers - Sleepy Hollow, NY
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

Hudson River Views: Briarcliff Manor Home W/ Deck - Sleepy Hollow, NY
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.
3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
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.
Stylish Tarrytown Studio - Walk To Train & Main St - Sleepy Hollow, NY
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.
1br Queen Near Nyc | Trails, Biking & Sauna Bliss - Sleepy Hollow, NY
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?

    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 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

3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
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.
3 Mi To Downtown Spacious White Plains Home - Sleepy Hollow, NY
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.
Beautiful Apartment 1 In Great Pleasantville, Ny - Sleepy Hollow, NY
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.
Hudson River Views Briarcliff Manor Home With Deck - Sleepy Hollow, NY
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

Upscale Downtown 2br | Lux Amenities | Laundry - Sleepy Hollow, NY
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.
Convenient Apt 2 Mi To Sprain Ridge Park! - Sleepy Hollow, NY
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.
Stylish 3br Home  Game Room  Free Parking  Sleeps 16 - Sleepy Hollow, NY
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.
Hudson River Views: Briarcliff Manor Home W/ Deck - Sleepy Hollow, NY
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.
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