Sleepy Hollow holiday homes

We found 267 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Sleepy Hollow that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
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Why visit Sleepy Hollow

  • Historic charm: Wander through storied streets, discovering Sleepy Hollow’s rich cultural heritage and enchanting past.
  • Scenic landscapes: Enjoy peaceful urban parks and natural reserves perfect for leisurely strolls and family picnics.
  • Arts and culture: Explore local arts centres that showcase the town’s creative spirit and community history.
  • Family-friendly atmosphere: Experience a welcoming, relaxed vibe ideal for both romantic getaways and family adventures.
  • Neighbourhood exploration: Discover diverse local areas offering a mix of business and leisure experiences in a quaint setting.

Top attractions near Sleepy Hollow

Sleepy Hollow, New York offers a unique blend of outdoor charm and cultural heritage, making it ideal for family adventures and romantic getaways. Explore its urban parks, historic sites, and arts centres to immerse yourself in the local legacy and picturesque landscapes. Discover the spirit of Sleepy Hollow as you wander through its storied streets and natural reserves for an unforgettable holiday experience.

  • Rockefeller Archive Center: This history museum offers a deep dive into the cultural and historical significance of the Rockefeller family, showcasing archives and exhibitions that reflect their impact on American society.
  • The Glass House: A stunning architectural masterpiece, this museum features beautiful landscapes and minimalist design, inviting visitors to appreciate the harmony between nature and modern living.
  • Marshlands Conservancy: A serene wetland area, perfect for family-friendly outings, where you can explore diverse ecosystems, enjoy scenic walks, and learn about local wildlife and history.

Things to do recommended for couples

For a romantic getaway in Sleepy Hollow, explore the enchanting trails of the Old Croton Aqueduct or enjoy a leisurely picnic at the scenic Kykuit estate. Don't forget to take a sunset cruise on the Hudson River, soaking in the stunning views together.

Things to do recommended for families

Families visiting Sleepy Hollow can explore the enchanting grounds of the historic Sleepy Hollow Cemetery, take a scenic stroll along the Hudson River at the Tarrytown Lakes, and enjoy interactive fun at the nearby Kykuit, the Rockefeller estate, perfect for a delightful family outing.

Things to do recommended for groups

Groups visiting Sleepy Hollow can enjoy a zipline and ropes course adventure at Palisades Climb Adventure, located 8km from town, offering an outdoor adventure perfect for group travellers.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Sleepy Hollow

Whether you're journeying with a group, travelling as a family, bringing your pets along, or seeking extended stays, be sure to filter your search based on the appropriate priorities. Here are some Vrbo booking tips to assist you.

  • Traveling to Sleepy Hollow with a group: Consider how many bedrooms you'll require, along with features like a fully equipped kitchen or an outdoor area for a group get-together. Luckily, you can search for all these options and more on Vrbo.
  • Traveling to Sleepy Hollow with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sleepy Hollow: For many families, a holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, have a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Sleepy Hollow: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Sleepy Hollow

Sleepy Hollow, New York, offers a charming blend of scenic outdoor spaces and family-friendly attractions. Visitors can explore the historic downtown area, stroll through tranquil streets, and enjoy a relaxed, romantic atmosphere. Whether you’re seeking a business vibe or a peaceful retreat, Sleepy Hollow’s diverse neighbourhoods provide a delightful experience for every traveller.

  • Briarcliff Manor: Situated 6km from Sleepy Hollow, Briarcliff Manor is a charming city that blends a family-friendly atmosphere with a vibrant city theme. Visitors can enjoy an array of outdoor activities while exploring its well-known shopping areas, centres, and malls. The local attractions, including a tourist precinct, square, and modern square, offer plenty of opportunities to stroll and take in the local culture, making it an ideal stop for those looking to mix leisure with a taste of urban life.
  • Piermont: Also 6km away from Sleepy Hollow, Piermont presents a delightful mix of outdoor, family, and city-themed experiences. This city is perfect for travellers keen on exploring urban parks, lakes, and theatres. With a shopping centre and mall centre on hand, visitors can enjoy a blend of retail therapy and scenic surroundings, while the nearby urban park and lake provide a refreshing escape into nature.
  • Dobbs Ferry: Located 8km from Sleepy Hollow, Dobbs Ferry offers a welcoming environment for families, outdoor enthusiasts, and urban explorers alike. The city's attractions include a mix of shopping areas, theatres, and centres, paired with local landmarks such as a tourist precinct, square, and modern square. This vibrant locale invites visitors to enjoy a balanced experience of city life and outdoor adventures.

Best time to go to Sleepy Hollow

If you're planning a trip to Sleepy Hollow, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January30.6°F (-0.8°C)Light RainMostly SunnyLow
February32.2°F (0.1°C)Light RainMostly SunnyLow
March39.6°F (4.2°C)Light RainMostly SunnyAverage
April50.5°F (10.3°C)Light RainMostly SunnyAverage
May60.8°F (16.0°C)Light RainMostly SunnyAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverage
July76.1°F (24.5°C)Light RainMostly SunnyAverage
August74.5°F (23.6°C)Light RainMostly SunnyHigh
September67.6°F (19.8°C)Light RainMostly SunnyHigh
October56.8°F (13.8°C)Light RainMostly SunnyHigh
November45.0°F (7.2°C)Light RainMostly SunnyAverage
December36.9°F (2.7°C)Light RainMostly SunnyLow

Booking with Vrbo is a breeze

Are you hoping to save some money on your next adventure? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient area for you to plan new trips, refine your existing arrangements, or manage your bookings. Your saved or booked properties are organised into categories such as Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Explore the riverfront setting in Sleepy Hollow

Enjoy the churches and other features of Sleepy Hollow. Renowned for its local tours, riverfront and hiking, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Sleepy Hollow

Do you want to find things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Sleepy Hollow has to offer. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Sportime USA (2.6 mi / 4.1 km)
  • Blue Hill Golf Course (7.1 mi / 11.4 km)
  • Rockland Bakery (7.4 mi / 11.9 km)
  • Legoland Discovery Center Westchester (8.3 mi / 13.3 km)
  • Rye Playland (12.7 mi / 20.4 km)
  • Bergen County Zoo (14.4 mi / 23.1 km)

Exploring the natural features in Sleepy Hollow

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Sleepy Hollow is a great place to get out in nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Rockefeller State Park Preserve (2 mi / 3.2 km)
  • Nyack Beach State Park (3.7 mi / 5.9 km)
  • Buttermilk Falls Park (4.6 mi / 7.4 km)
  • Rockland Lake State Park (4.6 mi / 7.5 km)
  • Tallman Mountain State Park (4.9 mi / 7.9 km)
  • Silver Lake Park (6.5 mi / 10.4 km)

Transport to and around Sleepy Hollow

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 8.1 mi (13.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Teterboro, NJ (TEB), which is 19.4 mi (31.2 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Sleepy Hollow?
The average price for a holiday home in Sleepy Hollow is determined by a number of factors, like length of stay, season and property type. Whether you're thinking about a sprawling house with room for friends and family or a comfy cabin perfect for just you and the kids, just enter your dates of travel to view stays with amazing value.
How much does it cost to rent a beach house in Sleepy Hollow?
Prices for beach houses in Sleepy Hollow differ depending on the size and style of the property and when you're travelling. All you need to do is enter your travel dates into Bookabach and how many guests to see your home options and prices. From there you can use our filters to narrow your search results by ratings, nearby activities and more.
What are the top attractions for families in Sleepy Hollow?
Keeping the kiddos entertained during your holiday in Sleepy Hollow is a snap with these exciting family-friendly attractions:

  • Rockefeller Archive Centre
  • Tarrytown Lighthouse
  • Tarrytown Music Hall

How old do you have to be to rent a holiday home in Sleepy Hollow?
The minimum required age is normally 16, 18 or 21. It can change from property to property on Bookabach, so look at the rules of your preferred Sleepy Hollow holiday home before making a booking.
How long can I rent a holiday home in Sleepy Hollow for?
It's up to the Sleepy Hollow property. To view all available options offering extended stays, just enter your travel dates and guest number into the Bookabach search page. Look forward to having the entire property to yourself, along with the comforts of home like a fully-equipped kitchen and a backyard where the kids can burn off energy. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.