Peekskill Summer Rentals, Cottages & Cabins

Book a Place to Stay in Peekskill for Your Summer Getaway

About Peekskill Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Peekskill 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 Peekskill 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™.

Show more
Show less

Frequently Asked Questions About Peekskill Luxury Rentals

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

In 2025, PickleTrip offers 76 summer rentals in or around Peekskill. 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 Peekskill is $441. Check the full list of summer accommodations in Peekskill.
There are 76 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 Peekskill that have a private or indoor pool:

Check all holiday rentals with a pool in Peekskill on PickleTrip.

Yes, We have 76 summer rental homes in Peekskill and types of place to stay in Peekskill include:

  • Vacation Homes: 76 available for rent
  • Villas: 76 Rentals available for rent
  • Holiday Apartments: 76 Rentals available for rent
  • Hotels with Suites: 76 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Peekskill. 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 Peekskill.