Windsor Summer Rentals, Cottages & Cabins

Book a Place to Stay in Windsor for Your Summer Getaway

About Windsor Summer Rental on PickleTrip

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

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

In 2026, PickleTrip offers 47 summer rentals in or around Windsor. 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 Windsor is $231. Check the full list of summer accommodations in Windsor.
There are 47 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 Windsor that have a private or indoor pool:

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

Yes, We have 47 summer rental homes in Windsor and types of place to stay in Windsor include:

  • Vacation Homes: 47 available for rent
  • Villas: 47 Rentals available for rent
  • Holiday Apartments: 47 Rentals available for rent
  • Hotels with Suites: 47 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Windsor. 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 Windsor.