1. USA
  2. Massachusetts
  3. Windsor
  4. Summer Rental

Windsor Summer Rentals, Cottages & Cabins

Book a Place to Stay in Windsor for Your Summer Getaway

About Windsor Summer Rental on Casai.com

With 182 summer rental in or near Windsor? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.

Our holiday homes and villas in Windsor come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.

Searching for a relaxing retreat in Windsor to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Windsor.

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 2025, Casai offers 182 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 $392. Check the full list of summer accommodations in Windsor.
There are 182 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.com.

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 Casai.com.

Yes, We have 182 summer rental homes in Windsor and types of place to stay in Windsor include:

  • Vacation Homes: 182 available for rent
  • Villas: 182 Rentals available for rent
  • Holiday Apartments: 182 Rentals available for rent
  • Hotels with Suites: 182 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.