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Winston Summer Rentals, Cottages & Cabins

Book a Place to Stay in Winston for Your Summer Getaway

About Winston Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Winston 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 Winston 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 Winston Luxury Rentals

There are a lot of options in Winston. If you plan on staying in the Winston area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Winston:

In 2025, PickleTrip offers 100 summer rentals in or around Winston. 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 Winston is $252. Check the full list of summer accommodations in Winston.
There are 100 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 Winston that have a private or indoor pool:

Check all holiday rentals with a pool in Winston on PickleTrip.

Yes, We have 100 summer rental homes in Winston and types of place to stay in Winston include:

  • Vacation Homes: 100 available for rent
  • Villas: 100 Rentals available for rent
  • Holiday Apartments: 100 Rentals available for rent
  • Hotels with Suites: 100 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Winston. 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 Winston.