Old Windsor Summer Rentals, Cottages & Cabins

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

About Old Windsor Summer Rental on SunSkiResorts

SunSki's selection of summer rentals in Old Windsor promises the ideal setting for your next seasonal escape. We offer a diverse array of properties boasting enticing features such as private pools, indoor/outdoor swimming facilities, hot tubs, WiFi, beachfront access, and more. Whether you're journeying with family, friends, or a larger group, we have a rental perfectly tailored to your requirements.

Immerse yourself in the epitome of summer leisure in Old Windsor with SunSki. Our summer rental accommodations are meticulously curated to ensure utmost comfort and relaxation. From chic condos and opulent resorts to charming villas, quaint bungalows, cozy cabins, RVs, and cottages, we present a spectrum of options to match your vacation vision. Discover your idyllic summer retreat with SunSki.

Show more
Show less

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, SunSki offers 441 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 $339. Check the full list of summer accommodations in Old Windsor.
There are 441 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with SunSkiResorts.

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 SunSkiResorts.

Yes, We have 441 summer rental homes in Old Windsor and types of place to stay in Old Windsor include:

  • Vacation Homes: 441 available for rent
  • Villas: 441 Rentals available for rent
  • Holiday Apartments: 441 Rentals available for rent
  • Hotels with Suites: 441 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.