Discover Your Perfect Sleepy Hollow Rentals by Owner

Sleepy Hollow Rentals by Owner

More Top-Rated Rentals by Owner in Sleepy Hollow Area

Why Choose Rent By Owner for your Sleepy Hollow vacation rental?

What makes our Rentals by Owner special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
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 Rentals by Owner stay?

Timing your vacation here can enhance your experience, so consider visiting during the shoulder seasons when the area offers a peaceful and authentic atmosphere ideal for relaxing stays in owner-managed rentals.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, this area experiences mild weather and blooming landscapes, making it an ideal time for exploring outdoor spaces and enjoying local charm.

Average Temperature Daytime: 55°F to 70°F - Nighttime: 40°F to 50°F
autumn
Fall (September to November)

Autumn in the region offers colorful foliage and pleasant temperatures, perfect for outdoor activities and experiencing seasonal events.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

image
Winter (December to February)

In winter, the area becomes quieter with cooler temperatures, providing a peaceful retreat for those who enjoy cozy accommodations and scenic winter views.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
image
Summer (June to August)

While summer brings warm weather and longer days, this is also when the region sees increased visitors, so early bookings are recommended for a more relaxed experience.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F

Weekly Weather Forecast for Sleepy Hollow

How to Book Your Sleepy Hollow vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner in Sleepy Hollow Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

  • Enjoy a spacious outdoor patio or deck, perfect for relaxing or entertaining amidst the scenic surroundings.
  • Take advantage of a private garden or yard where you can unwind and appreciate the natural beauty of the area.
  • Make use of a sparkling outdoor swimming pool to cool off during warmer months in this charming destination.
  • Fire up the barbecue grill for outdoor dining experiences that let you savor local flavors in the fresh air.
  • Benefit from well-maintained walking or hiking trails accessible from many rentals here, ideal for exploring the region's landscapes.
  • Relax in an outdoor seating area with picturesque views, providing a peaceful retreat after your adventures.
  • Utilize available outdoor recreational amenities such as a bocce ball court or a fire pit for cozy evenings under the stars.

Top Attractions Around Sleepy Hollow

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities, cultural experiences, and scenic walks that showcase the region’s historic charm and natural beauty, making your stay in Sleepy Hollow a memorable experience.

image
image

Family Activities

  • Sleepy Hollow Cemetery Tours: Explore the historic cemetery where you can learn about local legends and enjoy a respectful walk through this iconic resting place.
  • Vanderbilt Mansion National Historic Site: Discover the grandeur of this historic estate, offering family-friendly guided tours that showcase the region’s rich architectural heritage.
  • Horseback Riding in the Area: Enjoy scenic horseback riding experiences suitable for families, providing a fun way to explore the natural beauty surrounding here.
  • Local Nature Trails and Parks: Spend quality time outdoors on well-maintained trails perfect for hiking or picnicking, allowing your family to connect with the region’s lush landscape.
image

Adult Activities

  • Visit the Sleepy Hollow Cemetery: Explore this historic cemetery renowned for its legendary connections and beautifully maintained grounds, offering a peaceful retreat in the area.
  • Take a Trolley Tour of Tarrytown: Discover the region’s rich history and scenic beauty through guided trolley tours that highlight notable landmarks and local stories.
  • Explore the Old Dutch Church: Appreciate the architecture and historical significance of this centuries-old church, which provides insight into the area's colonial past.
  • Enjoy a Riverfront Walk along the Hudson River: Stroll along the picturesque riverfront to immerse yourself in stunning views and the natural beauty that surrounds this destination.

Other Places to Stay in Sleepy Hollow, NY

Tarrytown Lighthouse
Explore 79 Properties
Philipsburg Manor
Explore 76 Properties
Old Dutch Church of Sleepy Hollow
Explore 70 Properties
Sleepy Hollow Cemetery
Explore 55 Properties
Phelps Hospital
Explore 31 Properties
Phelps Memorial Hospital Center
Explore 30 Properties
More Places to Stay Near Sleepy Hollow

Sleepy Hollow Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar when booking your rental to make the most of regional festivals and celebrations during your stay in this historic destination.
  • Choose a Well-Located Rental: Select a property that offers easy access to points of interest and transportation options, ensuring you can explore comfortably throughout your visit here.
  • If Staying Near Waterfronts: Opt for a rental close to scenic water views, allowing you to enjoy peaceful mornings and picturesque sunsets during your time in this region.
  • Engage with Local Hosts: Communicate with your host before arrival to receive personalized tips on hidden gems and best practices for enjoying your stay in this unique part of New York State.

Transportation Options

  • Metro-North Railroad: You can conveniently access the regional rail service here, providing direct transportation to New York City and surrounding areas for easy day trips.
  • Local Bus Services: The region’s local bus options offer affordable and reliable transit throughout Sleepy Hollow and nearby towns, making short-distance travel seamless.
  • Rental Car Services: Several rental agencies operate within reach, giving you the flexibility to explore at your own pace beyond the immediate area.
  • Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available in the region, offering convenient door-to-door transportation for your needs.

Local Customs Options

  • Historic Vigilance: Respect the area's rich history by participating in or observing local commemorations, especially around the legendary stories that shape this destination.
  • Seasonal Celebrations: Engage in seasonal festivities like fall harvest events and holiday parades, which highlight the region's vibrant community spirit.
  • Respect for Nature: Practice environmental respect when exploring the scenic outdoor spaces, ensuring preservation of the area's natural beauty and tranquility.
  • Local Artistry: Support regional artisans by visiting local shops or markets that celebrate the area's creative heritage and craftsmanship.

Frequently Asked Questions About Sleepy Hollow Rentals by Owner

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. 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 32 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. 

3. What is the cancellation policy for a rental by owner in Sleepy Hollow?

Cancellation policies vary by individual listing. Please review the specific property's terms on the Rent By Owner platform or contact the owner directly to understand the cancellation rules and any applicable fees.

4. How do I communicate with the property owner before booking my stay?

You can use the messaging feature on the Rent By Owner platform to ask questions, clarify details, or request additional information about the rental in this part of the region. Owners are typically responsive to ensure your stay meets expectations.

5. Are there any specific amenities included in rentals around here?

Amenities differ from one rental to another. To find out what is included, such as Wi-Fi, parking, or kitchen facilities, please refer to the listing details or contact the owner directly before completing your booking.

6. What are the check-in and check-out procedures for rentals in this area?

Check-in and check-out times are specified on each listing. For any special arrangements or questions regarding arrival or departure, reach out to the owner beforehand to ensure a smooth process during your stay.

7. Is there a minimum stay requirement for booking a rental in this destination?

Minimum stay requirements depend on the individual property. You should review the listing's policy or contact the owner directly if you have specific dates in mind to confirm availability and length of stay restrictions.

More Rentals You May Like Near Sleepy Hollow

New
House
Bohemian Garden Cottage
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities
View Availability
More Top-Rated Rentals by Owner in Sleepy Hollow Area