1. Jamaica
  2. Trelawny
  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 Rent By Owner

With 385 summer rentals in or near Windsor, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Windsor or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Windsor for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Windsor, RBO has got you covered for your next summer holiday.

Show more
Show less

Frequently Asked Questions About Windsor Luxury Rentals

In 2025, RBO offers 385 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 $349. Check the full list of summer accommodations in Windsor.
There are 385 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

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 Rent By Owner.

Yes, We have 385 summer rental homes in Windsor and types of place to stay in Windsor include:

  • Vacation Homes: 385 available for rent
  • Villas: 385 Rentals available for rent
  • Holiday Apartments: 385 Rentals available for rent
  • Hotels with Suites: 385 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.