448+ Pet Friendly Hotels and Vacation Rentals in Winchester |
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  2. Virginia
  3. Winchester

Winchester Pet Friendly Vacation Rentals

About Winchester Vacation Rentals

There are more than 448 places to stay in Winchester and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Winchester.

Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Winchester, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Winchester. Places to stay near Winchester are 1165.53 ftΒ² on average, with prices averaging $352 a night.

PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Winchester with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.

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Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Winchester

Type Count
Vacation Homes 183
Holiday Apartments 63
Villas 16
Cottages 15

Use these Quick Filters to Find a Vacation Rental in Winchester

β˜… Pro Tip: PetFriendlyβ„’ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Winchester.

Weather in Winchester, VA

View the weather forecast for Winchester before booking your hotel or rental.

December - February
High 60Β°F       Low 26Β°F
March - May
High 77Β°F       Low 40Β°F
June - August
High 91Β°F       Low 64Β°F
September - November
High 84Β°F       Low 38Β°F

Stay Near Winchester, VA

PetFriendly finds and compares Pet-Friendly hotels, rentals, and resort listings near many of Winchester's attractions.


SheNonedoah University
Front Royal Entrance SheNonedoah National Park
Winchester Medical Center
Bluemont Vineyard
Skyline Caverns
Dinosaur Land
Apple Blossom Mall
Mt Hebron Cemetery
Jim Barnett Park
SheNonedoah Valley Discovery Museum
Wilson's Wild Animal Park
Patsy Cline Historic House
Twin Oaks Tavern Winery
Blue Ridge Arts Council and Gallery
Bing Crosby Stadium
Watermelon Park Campground
Winchester Little Theater
Holy Cross Abbey
Mackintosh Fruit Farm
Hupp's Hill Civil War Park

Other Places to Stay in Winchester, VA


Frederick County 162 Properties
Warren County 155 Properties
Front Royal 146 Properties
Happy Creek 141 Properties
Old Town Winchester 126 Properties
Strasburg 62 Properties
Paris 59 Properties
Clarke County 57 Properties
Berryville 37 Properties
Bluemont 34 Properties
Russell 27 Properties
Stephens City 25 Properties

Frequently Asked Questions About Winchester?

What are the top vacation rentals in Winchester?

Find the best options in or near Winchester for pet-friendly travel. If you are planning a trip or vacation in Winchester, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Winchester:

How many vacation rentals have private pools in Winchester?

We have found 1 accommodation options with private pools in or near Winchester, many of which accept and welcome pets. Top-rated hotels, resorts,and places to stay that have access to a swimming pool include:

Which vacation homes in Winchester are best for families?

Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Winchester? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Winchester:

How many PetFriendly vacation rentals are available in Winchester?

PetFriendlyβ„’ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2025 is over 448 in the Winchester area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Winchester.


People Also Ask

There are 448 Winchester, VA Vacation Rentals

Recently Booked Pet Friendly Hotels and Vacation Rentals in Winchester