Winchester pet-friendly rentals

We found 408 pet-friendly rentals — enter your dates for availability

Find spaces that suit your style

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  • More quality time

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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

Are there any pet-friendly holiday rentals in Winchester?
Browse our 408 pet-friendly holiday rentals and start organising your trip to Winchester. Whether you'd like to stay in Old Town Winchester, College Park, Kernstown or another popular neighbourhood, you'll find the perfect house for you and your furry friend on Stayz.
How much does it cost to stay in a pet-friendly holiday rental in Winchester?
To help find a pet-friendly holiday 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 accommodation 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 holiday rental in Winchester?
Many of our guests enjoy bringing their furry friend to Winchester, Frederick County in August. As our pet-friendly holiday 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 17ºC to 29ºC. If there are limited options, check our availability in other months.
Where can I rent a pet-friendly holiday rental with great views?
Get away to a pet-friendly holiday 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 holiday rentals in Winchester have a garden?
To find pet-friendly holiday 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 Stayz 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 Stayz's pet-friendly holiday rentals so every member of your crew can enjoy the trip together.
Why should I book my pet-friendly holiday rental with Stayz?
No sharing your space, no dealing with people you don't know. When you select a Stayz pet-friendly holiday rental, you get the entire place for just you and your furry friend. Need to cancel or alter your plans? Our flexible cancellation policies mean you can book your rental house with complete peace of mind.
Pet-friendly Rentals in Winchester
Pet-friendly Rentals in Old Town Winchester