Old Windsor Summer Rentals, Cottages & Cabins

Book a Place to Stay in Old Windsor for Your Summer Getaway

About Old Windsor Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Old 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 Old 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™.

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Frequently Asked Questions About Old Windsor Luxury 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 Summer Rentals in Old Windsor:

In 2025, PickleTrip offers 447 summer rentals in or around Old 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 Old Windsor is $338. Check the full list of summer accommodations in Old Windsor.
There are 447 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 Old Windsor that have a private or indoor pool:

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

Yes, We have 447 summer rental homes in Old Windsor and types of place to stay in Old Windsor include:

  • Vacation Homes: 447 available for rent
  • Villas: 447 Rentals available for rent
  • Holiday Apartments: 447 Rentals available for rent
  • Hotels with Suites: 447 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Old 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 Old Windsor.