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  2. Trelawny
  3. Windsor
  4. Beach Home Rentals

Windsor Beach House Rentals & Places to Stay

Find the best beach rentals in Windsor - We found 192 exact matches

About Windsor Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Windsor? PickleTrip™ features more than 192 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Windsor. Several of these vacation rentals in Windsor are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Windsor.

PickleTrip™ Offers 192 holiday homes and places to stay in Windsor. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Windsor Beach 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 Beach Home Rentals in Windsor:

The average cost for a beach rental in Windsor is $442 per night. PickleTrip has a wide assortment of great beachfront homes near Windsor that would suit your needs.
Yes, we have 192 beach rentals with pools available in Windsor. Check our search bar to find a selection of vacation rentals available near Windsor.
Yes, here are the top beach rentals in Windsor that allow you to bring your pet:

See all pet-friendly beach rentals in Windsor on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Windsor to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 192 properties with private swimming pools or private homes with indoor pools in the Windsor area.
About 192 properties in Windsor boast of having access to hot tubs.