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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 Rent By Owner

With 53 summer rentals in or near Winston, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Winston or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Winston for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Winston, RBO has got you covered for your next summer holiday.

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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 2026, RBO offers 53 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 $178. Check the full list of summer accommodations in Winston.
There are 53 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

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 Rent By Owner.