Winchester pet-friendly rentals

We found 410 pet-friendly rentals — enter your dates for availability

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Frequently asked questions

Are there any pet-friendly vacation rentals in Winchester?
Browse our 410 pet-friendly vacation rentals and start organizing your trip to Winchester. Whether you'd like to stay in Old Town Winchester, College Park, Kernstown or another popular neighborhood, you'll find the perfect house for you and your furry friend on Vrbo.
How much does it cost to stay in a pet-friendly vacation rental in Winchester?
To help find a pet-friendly vacation rental in Winchester that works with your budget, make full use of our comprehensive filters. Choose the maximum amount you want to spend and compare the prices of accommodations that have everything you need for the perfect stay with your pup. Bigger properties with several bedrooms and a bunch of amenities usually cost more, so pick something smaller if you want to save.
When is the best time to book a pet-friendly vacation rental in Winchester?
Many of our guests enjoy bringing their furry friend to Winchester, Frederick County in August. As our pet-friendly vacation rentals experience a high number of bookings during this month, we recommend you start searching as early as possible. Wondering what the temperatures will be at this time of year? Typically, they range from 62ºF (17ºC) to 84ºF (29ºC). If there are limited options, check our availability in other months.
Where can I rent a pet-friendly vacation rental with great views?
Get away to a pet-friendly vacation rental that not only welcomes your beloved pup, but also boasts unforgettable vistas. Check out our selection of Winchester stays that come with views of historic areas. Many also have outside spaces where you and your furry sidekick can frolic amid postcard-worthy surroundings.
Do any pet-friendly vacation rentals in Winchester have a garden?
To find pet-friendly vacation rentals in Winchester with an outdoor space, select "Garden or backyard" under the features and amenities filter. Some of our properties come with fenced gardens, while others are near trails, parks or other pet-friendly areas.
Can I book a pet-friendly cabin or lodge in Winchester?
Get back to nature with your faithful furry friend right by your side at one of our pet-friendly cabins or lodges in Winchester. Use our "Pet-friendly" filter to search for Vrbo properties that ensure an unforgettable experience for the entire family --- four-legged members included.
What are the top things to do in Winchester?
The family will enjoy visiting top-rated attractions like Summit Point Motorsports Park and Museum of the Shenandoah Valley during your trip to Winchester. If you have time for one more stop, Apple Blossom Mall is another one for your itinerary. And you don't have to leave Fido home alone. Book one of Vrbo's pet-friendly vacation rentals so every member of your crew can enjoy the trip together.
Why should I book my pet-friendly vacation rental with Vrbo?
When you stay in a Vrbo pet-friendly vacation rental, the only people you'll share your living space with are whoever you take with you. You and your furry friend will have the entire place to yourselves. Our flexible cancellation policies also mean you can book your rental house with peace of mind if you have to change your plans. And remember, if you join our One Key™ rewards program, you'll be able to earn and redeem OneKeyCash™* on eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.

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