Vacation 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
A$984/nighttotal: A$4920 (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.
Cozy Studio With Reading Nook - Sleepy Hollow, NY
9.8 8 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$291/nighttotal: A$1455 (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.
Perfect Family Getaway / 5br Home / 6 Queen Beds / Free Parking - Sleepy Hollow, NY
Sleepy Hollow, NY
23/10 – 26/10
A$1232/nighttotal: A$3696 (3 )

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

5 6
apartment , Yonkers
This expansive five-bedroom residence is situated in Yonkers' Bryn Mawr district, offering convenient access to landmarks such as the Bronx Zoo, located approximately 3.2 kilometres away, and the Untermyer Gardens Conservancy, about 2.4 kilometres distant.
This private home accommodates up to 20 guests with six queen beds, featuring a fully equipped kitchen, complimentary on-site parking, and air conditioning, making it a suitable option for families and groups seeking a comfortable stay in Yonkers.
Westchester Summer: Pool Pet Friendly Events Games - Sleepy Hollow, NY
9.2 31 reviews
Sleepy Hollow, NY
23/10 – 26/10
A$1982/nighttotal: A$5946 (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.

Best Sleepy Hollow, NY holiday rentals with parking

Beautiful & Fun Waterfront Duplex On The Hudson - Sleepy Hollow, NY
9.7 156 reviews
Sleepy Hollow, NY
17/08 – 27/08
A$676/nighttotal: A$6760 (10 )

Beautiful & Fun Waterfront Duplex On The Hudson

1 3
apartment , Nyack
This charming waterfront property is situated in Nyack, a historic river town, with easy access to the Hudson River and the Mario Cuomo Bridge. The apartment has received excellent ratings for location, cleanliness and user experience.
The dwelling has three bedrooms and one bathroom, accommodating up to four guests. Amenities include a fully equipped kitchen, a spacious living area with a fireplace, a private garden with a fire pit, and a 36 ft deck offering breathtaking views of the river and the bridge.
3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
Sleepy Hollow, NY
17/08 – 27/08
A$797/nighttotal: A$7970 (10 )

3 Mi To Downtown: Spacious White Plains Home

1 3
cottage , Fairview
This Fairview cottage is conveniently located within a 4.8km radius of Greenburgh Public Library, Westchester County Center, Pace University Law School, The Galleria at White Plains, and Blythedale Children's Hospital.
The self-catering property boasts a fully equipped kitchen with microwave and dishwasher, 2.5 bathrooms, a private balcony, garden, parking, and Wi-Fi; nearby attractions include an on-site arcade.
3 Mi To Downtown: Spacious White Plains Home - Sleepy Hollow, NY
9.2 15 reviews
Sleepy Hollow, NY
17/08 – 27/08
A$740/nighttotal: A$7400 (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.
Historic Former Speakeasy 4 Bdrm, Walk To Train And Town: Pleasantville - Sleepy Hollow, NY
Sleepy Hollow, NY
17/08 – 27/08
A$1324/nighttotal: A$13240 (10 )

Historic Former Speakeasy 4 Bdrm, Walk To Train And Town: Pleasantville

4 3
apartment , Pleasantville
This Pleasantville castle, a former speakeasy, is conveniently located a short walk from restaurants, a farmer's market, and a yoga studio, and within 1.6km of Rockefeller State Park and 3.2km of Stone Barns Center for Food and Agriculture.
This 372 square metre property boasts four bedrooms, four bathrooms, and accommodates up to ten guests, featuring a chef's kitchen, wood-burning fireplace, spa, terrace, garden, and parking, alongside easy access to hiking trails in Graham Hills Park and a 50-minute train journey to Grand Central Terminal in New York City.

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! You have to visit the iconic Sleepy Hollow Cemetery, where Washington Irving is buried, and the Old Dutch Church, which inspired his famous story. For something a little different, head to the Philipsburg Manor, a restored 18th-century estate with a working gristmill.
  • 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 paved path for walking or cycling, stretching for 40 kilometres through beautiful scenery. For a shorter walk, the Sleepy Hollow Cemetery itself is a lovely place to wander, with its historic monuments and peaceful atmosphere.
  • 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! You can enjoy hiking and biking in the Rockefeller State Park Preserve, which borders the village. The Hudson River offers opportunities for kayaking, paddleboarding, and even fishing.
  • 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 interesting places. You can easily visit Tarrytown, just across the river, which has a charming historic district and a vibrant arts scene. A little further afield, you can explore the city of Yonkers, or head into New York City, which is about an hour away by train.
  • 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, including kitchens, laundry facilities, and Wi-Fi. Many also have outdoor spaces like patios or balconies, perfect for enjoying the fresh air. Some even come with fireplaces or hot tubs for a more luxurious experience.
  • 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. Spring and autumn offer mild weather and stunning foliage. Summer is great for outdoor activities, while winter brings a magical atmosphere with snow-covered landscapes and festive events.
  • 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 restaurants serving fresh, seasonal dishes, often featuring local ingredients. Try the Hudson Valley apple pie, a classic treat, or a hearty stew with locally sourced vegetables.

Destinations nearby

Best Sleepy Hollow, NY holiday rentals with a balcony

Piermont Oasis - Sleepy Hollow, NY
9.8 18 reviews
Sleepy Hollow, NY
30/09 – 07/10
A$227/nighttotal: A$1589 (7 )

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.
557 M² Apartment ∙ 5 Bedrooms ∙ 13 Guests - Sleepy Hollow, NY
Sleepy Hollow, NY
23/10 – 26/10
A$2180/nighttotal: A$6540 (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.
Modern 4bd/3ba W/parking & Deck & 29 Min>nyc - Sleepy Hollow, NY
9.7 292 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$1085/nighttotal: A$5425 (5 )

Modern 4bd/3ba W/parking & Deck & 29 Min>nyc

3 2
apartment , Yonkers
This family-friendly house is located in Yonkers, a short drive from Hastings-on-Hudson and close to attractions like Untermyer Gardens Conservancy and the Hudson River Museum. The property has excellent user, location, and cleanliness ratings.
The house has three bedrooms and is 102 square metres in size. It offers a range of amenities including a swimming pool, tennis court, and a fully equipped kitchen, perfect for a comfortable and enjoyable stay.
Hudson River Views Briarcliff Manor Home With Deck - Sleepy Hollow, NY
10 2 reviews
Sleepy Hollow, NY
08/08 – 13/08
A$2304/nighttotal: A$11520 (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

Pet Friendly Parks & Trails Pleasantville Home - Sleepy Hollow, NY
Sleepy Hollow, NY
17/08 – 27/08
A$816/nighttotal: A$8160 (10 )

Pet Friendly Parks & Trails Pleasantville Home

1 3
apartment , Pleasantville
This Pleasantville flat offers a prime location, a 15-minute walk from the Jacob Burns Film Centre and within 5 kilometres of Rockefeller State Park Preserve and St John's River Side Hospital.
This property provides complimentary Wi-Fi, in-unit washing machines, Smart TVs, and fully equipped kitchens, making it ideal for a convenient stay with pets welcome.
Global Luxury Suites White Plains - Sleepy Hollow, NY
Sleepy Hollow, NY
27/06 – 04/07
A$466/nighttotal: A$3262 (7 )

Global Luxury Suites White Plains

1 2
apartment , White Plains
This apartment is conveniently located in White Plains, just one kilometre from the city centre, making it easy to explore the area's attractions.
The apartment is suitable for up to two guests and includes a kitchen with a microwave oven and dishwasher, as well as a garden and an outdoor pool. You can also enjoy free Wi-Fi, a laundry facility and a business centre during your stay.
Spacious Yonkers Home Sleeps 16  Game Room  Gazebo  Perfect For Groups - Sleepy Hollow, NY
Sleepy Hollow, NY
27/06 – 04/07
A$2225/nighttotal: A$15575 (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.
Charming Dobbs Ferry (Westchester) Victorian Home - Sleepy Hollow, NY
9.4 10 reviews
Sleepy Hollow, NY
30/09 – 07/10
A$754/nighttotal: A$5278 (7 )

Charming Dobbs Ferry (Westchester) Victorian Home

1 2
apartment , Dobbs Ferry
This Dobbs Ferry apartment, situated opposite Gould Park, is 0.8km from the village centre and 1.6km from the train station, offering easy access to Manhattan via a 35-minute train journey.
Sleeping up to nine guests, this four-bedroom, one-bathroom Victorian house boasts a spacious layout with two king-size and one single bed, a second living area, full kitchen, BBQ, laundry facilities, and ample street parking; it also benefits from a large garden and is available for short or discounted long-term lets.
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