New Windsor Summer Rentals, Cottages & Cabins

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

About New Windsor Summer Rental on PickleTrip

PickleTrip™'s summer rentals in New 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 New 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 New Windsor Luxury Rentals

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

In 2025, PickleTrip offers 157 summer rentals in or around New 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 New Windsor is $206. Check the full list of summer accommodations in New Windsor.
There are 157 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 New Windsor that have a private or indoor pool:

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

Yes, We have 157 summer rental homes in New Windsor and types of place to stay in New Windsor include:

  • Vacation Homes: 157 available for rent
  • Villas: 157 Rentals available for rent
  • Holiday Apartments: 157 Rentals available for rent
  • Hotels with Suites: 157 Rentals available for book
Yes, of course! There are many luxury summer rental properties in New 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 New Windsor.