Old Windsor Beach House Rentals & Places to Stay

Find the best beach rentals in Old Windsor - We found 13 exact matches

About Old Windsor Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Old Windsor? PickleTrip™ features more than 13 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Old Windsor. Several of these vacation rentals in Old 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 Old Windsor.

PickleTrip™ Offers 13 holiday homes and places to stay in Old 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 Old Windsor Beach Rentals

There are a lot of options in Old Windsor. If you plan on staying in the Old 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 Old Windsor:

The average cost for a beach rental in Old Windsor is $366 per night. PickleTrip has a wide assortment of great beachfront homes near Old Windsor that would suit your needs.
Yes, we have 13 beach rentals with pools available in Old Windsor. Check our search bar to find a selection of vacation rentals available near Old Windsor.
Yes, here are the top beach rentals in Old Windsor that allow you to bring your pet:

See all pet-friendly beach rentals in Old 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 Old Windsor to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 13 properties with private swimming pools or private homes with indoor pools in the Old Windsor area.
About 13 properties in Old Windsor boast of having access to hot tubs.