Discover Your Perfect Sleepy Hollow Vacation Homes

Best Vacation Homes in Sleepy Hollow

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Sleepy Hollow Luxury Rentals

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Find More Sleepy Hollow Villas, Resorts, & Rentals on BedroomVillas

Why Choose Rent By Owner for your Sleepy Hollow Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Sleepy Hollow

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you experience the region's charm at its best, with seasonal variations offering unique opportunities for exploring and enjoying your stay in Sleepy Hollow, Tarrytown, New York.

Peak Season Highlights

autumn
Fall (September to November)

During the vibrant autumn months, the region offers picturesque landscapes and a cozy atmosphere, making it an ideal time to explore and enjoy your stay here.

Average Temperature Daytime: around 65°F to 75°F - Nighttime: about 50°F to 60°F
summer
Summer (June to August)

The warm summer season attracts visitors seeking pleasant weather for outdoor activities and relaxing stays in this charming area.

Average Temperature Daytime: approximately 80°F to 85°F - Nighttime: around 60°F to 70°F

Off-Season Highlights

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Winter (December to February)

Cold winter months bring quieter accommodations and a peaceful ambiance, perfect for those looking to escape the crowds and enjoy serene surroundings.

Average Temperature Daytime: roughly 30°F to 40°F - Nighttime: about 20°F to 30°F
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Early Spring (March to April)

As the region transitions from winter, early spring presents fewer tourists and a chance to experience blooming nature at a slower pace.

Average Temperature Daytime: around 45°F to 55°F - Nighttime: approximately 35°F to 45°F

Weekly Weather Forecast for Sleepy Hollow

How to Book Your Sleepy Hollow Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Sleepy Hollow

More Top-Rated Vacation Rentals in Sleepy Hollow Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Privately enclosed outdoor spaces perfect for relaxing or entertaining in the fresh air
  • Accessible outdoor dining areas such as patios or decks for enjoying meals outdoors
  • Beautifully maintained gardens or landscaped yards to explore and unwind in
  • Outdoor fire pits or fireplaces ideal for cozy evenings under the stars
  • Spacious lawns or grassy areas suitable for outdoor activities and games
  • Dedicated grilling stations or barbecue setups for summer cookouts
  • Seating areas with scenic views to soak in the natural beauty of the region

Top Attractions Around Sleepy Hollow

What attractions are nearby?

Within this charming region, you can explore a variety of cultural and outdoor activities that showcase the rich history and natural beauty nearby, making your stay in Sleepy Hollow an unforgettable experience.

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Family Activities

  • Sleepy Hollow Cemetery: Explore this historic cemetery with its captivating stories and beautiful landscapes, perfect for family outings in the region.
  • The Great Jack-o'-Lantern Blaze: Experience an enchanting evening as the area's renowned display of illuminated pumpkins creates a festive atmosphere for all ages.
  • Phillipse Manor Hall State Historic Site: Discover local history through engaging tours at this well-preserved historic mansion that offers a glimpse into the past here.
  • Tarrytown Lakes Park: Enjoy outdoor fun with hiking, picnicking, and fishing opportunities surrounded by scenic views in this family-friendly area nearby.
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Adult Activities

  • Sleepy Hollow Cemetery Tour: Explore the historic grounds and learn about the area's fascinating folklore and famous inhabitants.
  • Historic Tarrytown Walks: Embark on guided or self-guided tours through the charming streets filled with architecture reflecting the area's rich history.
  • Hudson River Cruises: Enjoy scenic boat rides along the river for breathtaking views of the region’s natural beauty and historical landmarks.
  • Horseback Riding at Rockefeller State Park Preserve: Experience the tranquility of this expansive park while riding through scenic trails that showcase the area's lush landscape.

Other Places to Stay in Sleepy Hollow, NY

Tarrytown Lighthouse
Tarrytown Lighthouse Vacation Rentals
Philipsburg Manor
Philipsburg Manor Vacation Rentals
Old Dutch Church of Sleepy Hollow
Old Dutch Church of Sleepy Hollow Vacation Rentals
Sleepy Hollow Cemetery
Sleepy Hollow Cemetery Vacation Rentals
Phelps Hospital
Phelps Hospital Vacation Rentals
Phelps Memorial Hospital Center
Phelps Memorial Hospital Center Vacation Rentals
More Places to Stay Near Sleepy Hollow

Sleepy Hollow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of the region's historic sites and scenic spots to fully appreciate the area's unique charm.
  • Plan Your Activities: Schedule outdoor adventures or cultural experiences early to maximize your time and enjoy the best this destination has to offer.
  • Book in Advance: Secure your ideal vacation rental ahead of time to ensure a comfortable and convenient stay in this popular travel region.
  • Discover Nearby Dining: Sample local cuisine at nearby restaurants to immerse yourself in the area's culinary traditions during your visit.

Transportation Options

  • Metro-North Railroad:** This regional train service offers convenient connections from Sleepy Hollow to New York City and other major hubs, making it an ideal transportation choice for exploring the area without a car.
  • Local Bus Services:** Local bus routes provide affordable and accessible transportation within Tarrytown and nearby neighborhoods, helping you easily reach popular attractions and amenities in the region.
  • Driving and Car Rentals:** Renting a car or driving your own allows flexible exploration of Sleepy Hollow and the surrounding area, giving you the freedom to visit scenic spots and historic sites at your own pace.
  • Taxi and Ride-Sharing Services:** Taxis and ride-sharing options like Uber and Lyft are readily available here, offering quick and reliable transit for short trips around Sleepy Hollow and Tarrytown.

Local Customs Options

  • Halloween Traditions: Embrace the region's spooky history with local Halloween festivities that draw visitors from around the world.
  • Historical Reenactments: Participate in or observe reenactments of historic events that celebrate the area's rich colonial past.
  • Folk Festivals: Enjoy seasonal folk festivals featuring traditional crafts, music, and food that reflect the area's cultural heritage.
  • Community Parades: Experience lively parades during local celebrations that foster a strong sense of community here.

Frequently Asked Questions About Sleepy Hollow?

1. What are the top vacation rentals in Sleepy Hollow?

There are a lot of options in Sleepy Hollow. If you plan on staying in the Sleepy Hollow area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sleepy Hollow:

2. Which vacation homes in Sleepy Hollow are best for families?

If you are looking for a family-friendly vacation home in Sleepy Hollow, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sleepy Hollow:

3. How many Rentbyowner vacation rentals are available in Sleepy Hollow?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 49 in the Sleepy Hollow area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Sleepy Hollow. 

4. What is the cancellation policy for a rental in Sleepy Hollow, Tarrytown?

Cancellation policies vary by listing, so you should review the specific terms outlined in the property’s description or contact the owner directly to understand the applicable cancellation rules and any associated fees.

5. How do I confirm the availability of my preferred vacation rental in this region?

Availability can fluctuate, so it’s best to check the property's calendar directly on the listing and reach out to the host if you have specific dates in mind to ensure your desired stay is confirmed.

6. Are there any special amenities included with rentals in the area?

Amenities differ between properties, so be sure to review the detailed listing for information on features like Wi-Fi, parking, or outdoor spaces, or contact the host for clarification before booking.

7. What is the process for checking into and out of a vacation rental here?

Check-in and check-out procedures are typically specified in the listing, but contacting the host ahead of time can provide you with detailed instructions to ensure a smooth arrival and departure experience.

8. How can I coordinate transportation to and from Sleepy Hollow or Tarrytown during my stay?

While transportation options may not be included, you can inquire with the host about local services or nearby transit links, and plan your arrival accordingly to make your stay more convenient.