Sleepy Hollow Summer Rentals, Cottages & Cabins

Book a Place to Stay in Sleepy Hollow for Your Summer Getaway

About Sleepy Hollow Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Sleepy Hollow are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Sleepy Hollow with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Sleepy Hollow Luxury Rentals

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 Summer Rentals in Sleepy Hollow:

In 2025, PickleTrip offers 1430 summer rentals in or around Sleepy Hollow. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Sleepy Hollow is $278. Check the full list of summer accommodations in Sleepy Hollow.
There are 1430 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Sleepy Hollow that have a private or indoor pool:

Check all holiday rentals with a pool in Sleepy Hollow on PickleTrip.

Yes, We have 1430 summer rental homes in Sleepy Hollow and types of place to stay in Sleepy Hollow include:

  • Vacation Homes: 1430 available for rent
  • Villas: 1430 Rentals available for rent
  • Holiday Apartments: 1430 Rentals available for rent
  • Hotels with Suites: 1430 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Sleepy Hollow. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Sleepy Hollow.