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Winchester Cottage Rentals & Golf course

Find the best cottages in Winchester - We found 191 exact matches

About Winchester Cottage Rentals on StayAndPlay

Looking for exceptional golf cottages near Winchester for your next getaway? StayAndPlay offers more than 191 unique golf retreats and luxury villas, perfect for your family or group trip. Discover accommodations set in scenic golf destinations, featuring amenities like private pools, championship course access, and spacious living areas. These rentals provide an exceptional experience, catering to families, friends, couples, or golf enthusiasts.

Planning a golf retreat or a getaway for your group? StayAndPlay provides a variety of accommodations, including top-rated golf cottages, private villas, and spacious vacation rentals, connecting you directly with property owners to secure the best rates.

Explore 191 premium golf stays and exclusive golf-friendly accommodations in Winchester with StayAndPlay. Find unique Airbnb-style and VRBO-style golf rentals perfect for your weekend escape, golf vacation, or corporate retreat, 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 $522 per night. StayAndPlay.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 StayAndPlay

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 StayAndPlay shows that there are Over 191 private swimming pools or cottages with indoor pools in the Winchester area along with other great amenities.
About 191 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 StayAndPlay
Yes, there are luxury cottages in Winchester. Find more luxury, lakefront, winter, & last-minute cottage rentals near Winchester.