Winchester Summer Rentals, Cottages & Cabins

Book a Place to Stay in Winchester for Your Summer Getaway

About Winchester Summer Rental on Float Homes

Looking for the perfect summer escape in Winchester? Float Homes offers a unique collection of floating home rentals, including houseboats, overwater villas, floating cabins and more. Our properties are equipped with luxurious amenities such as private decks, swimming pools, hot tubs, WiFi, and breathtaking water views. Whether you’re traveling with family, friends, or a larger group, our floating homes in Winchester provide the ideal setting for an unforgettable vacation.

Make the most of your summer getaway in Winchester with Float Homes. Our selection of floating accommodations ensures maximum comfort and relaxation. From elegant houseboats to private overwater villas and cozy floating cabins, each home offers a one-of-a-kind experience on the water. Find your perfect floating home for the ultimate summer retreat in Winchester with Float Homes.

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Frequently Asked Questions About Winchester Luxury Rentals

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

In 2025, FloatHomes.com offers 37 summer rentals in or around Winchester. 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 Winchester is $320. Check the full list of summer accommodations in Winchester.
There are 37 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Float Homes.

Yes, here are some popular summer holiday rentals in Winchester that have a private or indoor pool:

Check all holiday rentals with a pool in Winchester on Float Homes.

Yes, We have 37 summer rental homes in Winchester and types of place to stay in Winchester include:

  • Vacation Homes: 37 available for rent
  • Villas: 37 Rentals available for rent
  • Holiday Apartments: 37 Rentals available for rent
  • Hotels with Suites: 37 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Winchester. 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 Winchester.