Sleepy Hollow holiday homes

We found 245 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:

  • 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)
  • Ridgewood Country Club (15.1 mi / 24.3 km)
  • Bronx Zoo (16.3 mi / 26.3 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)
  • Croton Point Park (6.9 mi / 11.1 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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Sleepy Hollow holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Sleepy Hollow to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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