Sleepy Hollow holiday rentals

We found 247 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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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:

  • 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)
  • Glen Island Harbour Club (14.3 mi / 23 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)
  • Croton Point Park (6.9 mi / 11.1 km)
  • Untermyer Gardens Conservancy (8.4 mi / 13.5 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

What is the best area to stay in Sleepy Hollow when booking a holiday rental?
When considering a holiday rental in Sleepy Hollow, New York, the area around the Hudson River is particularly appealing. This picturesque neighbourhood not only boasts stunning views of the river but also provides easy access to some of the region's most celebrated attractions. One cannot miss the iconic Sleepy Hollow Cemetery, which is steeped in history and offers a serene landscape to explore. Additionally, the nearby Kykuit, the Rockefeller estate, showcases beautiful gardens and impressive art collections, making it a delightful day out.The properties in this area tend to vary, offering a range of charming options from quaint cottages to more modern homes. Staying near the river allows guests to enjoy leisurely strolls along the waterfront and experience the captivating scenery that the Hudson Valley is known for.
When is the best time to visit Sleepy Hollow for a holiday rental?
October is the most popular time to visit Sleepy Hollow, as it coincides with the enchanting fall foliage and the town's famous Halloween festivities. The peak season runs from August through October, attracting visitors eager to immerse themselves in the rich history and picturesque landscapes that Sleepy Hollow offers.During this period, you can enjoy the mild autumn temperatures, typically ranging from 10 to 15 degrees Celsius, making it ideal for outdoor activities such as hiking along the scenic trails of the nearby Rockefeller State Park Preserve or exploring the legendary Sleepy Hollow Cemetery. The vibrant colours of the changing leaves create a stunning backdrop for sightseeing and photography, enhancing your experience.If you're looking for a more affordable option, consider planning your visit in December. While this month is quieter, it allows for a great experience of the winter charm in Sleepy Hollow, with fewer crowds and the opportunity to enjoy the holiday decorations that adorn the historic sites.Ultimately, the best time to book a holiday rental in Sleepy Hollow hinges on your preference for bustling seasonal activities in October versus a peaceful winter escape in December.
What are the top attractions in Sleepy Hollow?
In Sleepy Hollow, visitors can experience firsthand the rich history and enchanting landscapes that define the area. The iconic Sleepy Hollow Cemetery is a must-visit, famous for its association with Washington Irving and the legendary Headless Horseman. Nearby, the stunning Kykuit estate, home to the Rockefeller family, offers guided tours of its beautiful gardens and art collections.The Old Dutch Church, a historic landmark, is another significant attraction, showcasing historic architecture and a serene cemetery. For those interested in nature, the scenic hiking trails at the Rockefeller State Park Preserve provide picturesque views and peaceful walks through woodlands and along the Pocantico River.
Are all fees included in the Sleepy Hollow holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Sleepy Hollow holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sleepy Hollow with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Sleepy Hollow holiday homes?
You can find great discounts on holiday homes in Sleepy Hollow on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Sleepy Hollow holiday home booking on Stayz?
To find Sleepy Hollow holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Sleepy Hollow?
A long-stay holiday home in Sleepy Hollow is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Sleepy Hollow holiday home?
Book your Sleepy Hollow holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Sleepy Hollow?
Prices for holiday homes in Sleepy Hollow vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Sleepy Hollow to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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