Discover Your Perfect Sleepy Hollow Vacation Homes

Sleepy Hollow Luxury Rentals

|
New
House
Robin Crest with Hot Tub
  • Security/Safety
  • Barbecue/Outdoor Cooking
  • Child Friendly
View Availability
See More Sleepy Hollow Luxury Vacation Rentals
Find More Sleepy Hollow Villas, Resorts, & Rentals on BedroomVillas

Sleepy Hollow Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Sleepy Hollow on PetFriendly.io

Sleepy Hollow Large Vacation Homes

See More Family Vacation Rentals in Sleepy Hollow on FVR

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

What makes our Vacation Rentals 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 Vacation Rentals stay?

Choosing the ideal time to visit ensures you enjoy the best experience in this destination, where seasonal weather and local events can enhance your stay in the area’s welcoming vacation rentals.

Peak Season Highlights

summer
Summer (June to August)

This is the most popular time to visit, as the warm weather and longer days make for ideal outdoor activities in the region. Expect higher demand for vacation rentals during this lively season.

Average Temperature Daytime: 85°F - Nighttime: 65°F
autumn
Fall (September to November)

The vibrant fall foliage attracts visitors seeking picturesque scenery and comfortable temperatures. It’s a peak period for enjoying the area's natural beauty in your vacation rental.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

image
Winter (December to February)

During the colder months, fewer travelers visit, offering a quieter experience. This is an excellent time to find deals on vacation rentals and enjoy peaceful surroundings.

Average Temperature Daytime: 40°F - Nighttime: 25°F
image
Early Spring (March to April)

As the region transitions into warmer weather, visitor numbers are lower. It’s a good opportunity to explore in a more relaxed setting with potentially better rates on vacation rentals.

Average Temperature Daytime: 55°F - Nighttime: 35°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

  • Enjoy outdoor dining areas perfect for relaxing meals amid the scenic surroundings
  • Take advantage of spacious patios or decks to unwind and entertain friends and family
  • Make the most of private yards or gardens for outdoor activities and playtime
  • Benefit from access to outdoor grills or BBQ setups for cookouts under the open sky
  • Relax in inviting swimming pools, ideal for warm days in this region
  • Explore well-maintained walking or biking paths nearby for outdoor adventures
  • Utilize outdoor fire pits or fireplaces for cozy evenings in the fresh air

Top Attractions Around Sleepy Hollow

What attractions are nearby?

Within this charming destination, you can enjoy a variety of outdoor activities and scenic spots that showcase the natural beauty of the region, making it an ideal place to explore during your stay.

image
image

Family Activities

  • Sleepy Hollow Nature Reserve: Explore scenic walking trails and enjoy outdoor activities in the peaceful setting that the area is known for.
  • Local Community Events: Participate in family-friendly festivals and gatherings that celebrate the region’s local culture and traditions.
  • Public Parks and Playgrounds: Spend quality time at well-maintained parks equipped with playgrounds, perfect for children to play and families to relax together.
  • Historic District Tours: Discover the charming history of this destination through guided walks and self-guided tours around its quaint historic neighborhoods.
image

Adult Activities

  • Hiking at River Trails Conservation Area: Enjoy scenic walks and nature observation along well-maintained trails that showcase the beauty of the local landscape.
  • Fishing and boating on the Des Plaines River: Spend a relaxing day engaging in fishing or paddling activities, making the most of this picturesque waterway.
  • Golfing at nearby courses: Test your golf skills at one of the region’s top golf courses, offering a challenging game amid tranquil surroundings.
  • Exploring local dining experiences: Discover a variety of restaurants that serve regional cuisine, perfect for unwinding after a day of exploring the area.

Other Places to Stay in Sleepy Hollow, IL

West Dundee
West Dundee Vacation Rentals
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 before your trip to optimize your stay and enjoy any special festivities or community activities in this destination.
  • Explore Nearby Nature Spots: Take advantage of the region’s natural beauty by visiting local parks or scenic trails that showcase the landscape surrounding your vacation rental here.
  • Discover Dining Options: Sample the local cuisine by exploring recommended restaurants within the area, enhancing your overall experience during your visit.
  • Choose a Prime Location: Select a vacation rental close to key attractions and conveniences to make the most of your time and reduce travel between your accommodations and activities.

Transportation Options

  • Metra commuter train: You can easily access Chicago and other regional destinations via the Metra train service that runs close to this area.
  • Local bus services: Public buses provide convenient transportation within the region, making it simple for you to explore nearby attractions without a car.
  • Car rental services: Renting a vehicle is a popular option here, offering flexibility to visit the wider region at your own pace.
  • Taxi and ride-sharing options: Taxis and ride-share apps like Uber and Lyft are readily available for quick and comfortable travel around this destination.

Local Customs Options

  • Traditional Halloween Celebrations: Embrace the area's festive spirit with local customs that highlight the region's famous Halloween traditions, perfect for seasonal visitors seeking an authentic experience.
  • Community Parades and Events: Participate in neighborhood parades and community gatherings that showcase the region’s close-knit charm and welcoming atmosphere.
  • Decorative Home Displays: Discover how residents here take pride in their creative and elaborate Halloween decorations, adding to the area's spooky appeal.
  • Historic Folklore and Stories: Explore local legends and folklore that have been passed down through generations, giving you a deeper connection to this destination’s cultural heritage.

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 68 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 vacation rentals in Sleepy Hollow, Illinois?

Cancellation policies vary by property, so it's best to review the specific listing details or contact the host directly to understand the terms related to your booking in this area.

5. How do I verify the availability of vacation rentals in Sleepy Hollow, Illinois?

Availability status is updated regularly on the listing page. You can check real-time availability by entering your desired dates and reaching out to the property owner for confirmation.

6. Are pets allowed in vacation rentals here, and what are the pet policies?

Pet policies differ between properties, so you'll need to review each listing's rules or contact the host directly to find out if pets are permitted during your stay in this region.

7. What amenities can I expect in vacation rentals located in Sleepy Hollow, Illinois?

Amenities vary by property; detailed descriptions are available on each listing. For specific needs, it’s recommended to contact the host or review the listing thoroughly to ensure your requirements are met.

8. How do I inquire about special requests or additional services for my stay?

You can reach out directly to the property owner through the booking platform to discuss any special requests or additional services you may need during your visit to the area.