Winchester cabins

We found 171 cabins — enter your dates for availability

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a cabin rental in Winchester?
Small or sprawling, basic or luxurious — Vrbo has cabin rentals for every budget. To find a getaway that matches yours, take advantage of our price filter. You can fine-tune your search results by the maximum nightly price or total price. The cost will vary depending on what sort of property you choose, but the one thing that stays the same? The joy that comes with spending your holiday in one of our Winchester cabin rentals.
When is the best time to book a cabin rental in Winchester?
It depends on the type of weather you prefer, among other factors. Many visitors to Frederick County book a Winchester cabin rental in August, when temperatures range from 17 ºC (63 ºF) to 29 ºC (84 ºF).
Where can I rent a Winchester cabin rental with great views?
Cabin rentals with views of historic areas are just one of the types of holiday properties available in Winchester. If you're searching for stays that come with vistas worth remembering, Vrbo will help you find them.
Does Winchester have any lake cabins?
Enjoy long, laid-back days by the water at one of our lake cabin rentals in Winchester. Try looking for properties around popular expanses such as Warden Lake. You'll get to experience lakeside living combined with outdoor activities like nature walks and bird-watching.
Can I book a luxury cabin in Winchester?
Enjoy a taste of the good life on your holiday to Winchester by opting for a luxe cabin rental. These upmarket properties indulge guests with first-class amenities like pools and hot tubs. Use our filters to look for cabins with high guest ratings and experience the outdoors without sacrificing comfort!
Can I book a cabin with a hot tub in Winchester?
Nothing says relaxation like slipping into the bubbles of a hot tub in your cabin rental. To find properties with this perk in Winchester, click on "Hot tub" in the features and amenities search filter. After a busy day of adventures in the great outdoors, pop open a bottle of Champagne and enjoy a long, soothing soak.
What are the top things to do in Winchester?
Summit Point Motorsports Park, Museum of the Shenandoah Valley and Apple Blossom Mall are popular attractions that'll keep the whole crew occupied in Winchester. There's nothing like a getaway to bring everyone together, so browse our cabin rentals in this exciting destination.
Why should I book my cabin rental with Vrbo?
No sharing your space, no dealing with strangers. When you stay in a Vrbo cabin rental, you have the whole place all to yourself. Need to amend or cancel your itinerary? Our flexible cancellation policies let you book your cabin with total peace of mind.