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Winchester Cottage Rentals & Holiday Homes

Find the best cottages in Winchester - We found 37 exact matches

About Winchester Cottage Rentals on Float Homes

Looking for charming lakeside or dock cottages near Winchester for your next getaway? Float Homes offers more than 37 luxury lakeside and dock cottage and floating home rentals, perfect for your family or group trip. Discover cottages located just a few steps from the water, featuring amenities like hot tubs, kid-friendly accommodations, and easy access to top local attractions. These rentals ensure an exceptional experience on the water, with options that cater to large groups, families, friends, or couples.

Planning a lakeside retreat or a water-based getaway for your group? Float Homes provides a variety of floating home rentals including dock and lakeside cottages, houseboats, floating cabins, and more, connecting you directly with owners to secure the best prices.

Explore 37 lakeside cottages and exceptional water-based accommodations in Winchester with Float Homes. Find unique Airbnb-style and VRBO-style cottages perfect for your weekend escape, spring break, or annual vacation, all within your budget.

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Frequently Asked Questions About Winchester Rental Cottages

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 Cottage Rentals in Winchester:

The average cost for a cottage rental in Winchester is $241 per night. FloatHomes.com has a wide list of great cottages near Winchester that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Winchester that allow you to bring your pet:

See all pet-friendly vacation rentals in Winchester on Float Homes

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Winchester to find one that works for you.
As of 2025, the data from Float Homes shows that there are Over 37 private swimming pools or cottages with indoor pools in the Winchester area along with other great amenities.
About 37 cottages in Winchester boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Winchester on Float Homes
Yes, there are luxury cottages in Winchester. Find more luxury, lakefront, winter, & last-minute cottage rentals near Winchester.