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Winchester Cottage Rentals & Holiday Homes

Find the best cottages in Winchester - We found 182 exact matches

About Winchester Cottage Rentals on Rent By Owner

Searching for cottages to rent near Winchester? Rent By Owner features more than 182 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Winchester have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. RBO’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Winchester.

Are you planning to travel to the lakeside, beach, or mountain area? RBO’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Rent By Owner boasts of 182 holiday cottages and places to stay in Winchester. The site provides unique Airbnb, VRBO, RBO-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting 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 $517 per night. RBO 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 Rent By Owner

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 Rent By Owner shows that there are Over 182 private swimming pools or cottages with indoor pools in the Winchester area along with other great amenities.