1. USA
  2. Illinois
  3. Chicago
  4. Douglas
  5. Summer Rental

Douglas Summer Rentals, Cottages & Cabins

Book a Place to Stay in Douglas for Your Summer Getaway

About Douglas Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Douglas 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 Douglas 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 Douglas Luxury Rentals

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

In 2026, PickleTrip offers 68 summer rentals in or around Douglas. 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 Douglas is $346. Check the full list of summer accommodations in Douglas.
There are 68 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 Douglas that have a private or indoor pool:

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

Yes, We have 68 summer rental homes in Douglas and types of place to stay in Douglas include:

  • Vacation Homes: 68 available for rent
  • Villas: 68 Rentals available for rent
  • Holiday Apartments: 68 Rentals available for rent
  • Hotels with Suites: 68 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Douglas. 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 Douglas.