81+ Pet Friendly Hotels and Vacation Rentals in Chester Gap |
  1. USA
  2. Virginia
  3. Winchester
  4. Chester Gap

Chester Gap Pet Friendly Vacation Rentals

About Chester Gap Vacation Rentals

There are more than 81 places to stay in Chester Gap 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 Chester Gap.

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 Chester Gap, 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 Chester Gap. Places to stay near Chester Gap are 948.78 ft² on average, with prices averaging US $313 a night.

PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Chester Gap 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 Chester Gap

Type Count
Vacation Homes 31
Holiday Apartments 23
Cottages 3
Villas 1

Use these Quick Filters to Find a Vacation Rental in Chester Gap

★ Pro Tip: PetFriendly™ 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 Chester Gap.

Weather in Chester Gap, VA

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

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

Stay Near Chester Gap, VA

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


Chester Gap Cellars
Front Royal Entrance SheNonedoah National Park
Little Washington Winery
Skyline Caverns
Dinosaur Land
Thorton Gap Entrance SheNonedoah
Yogi Bear's Jellystone Park
Cobbler Mountain Cellars
SheNonedoah River State Park
Barrel Oak Winery
Linden Vineyards
Delaplane Cellars
Wilson's Wild Animal Park
Virginia Wine Country Tours
Naked Mountain Winery & Vineyards
Blue Ridge Arts Council and Gallery
Bing Crosby Stadium
Watermelon Park Campground
Mary's Rock Summit Trailhead
Philip Carter Winery

Other Places to Stay in Chester Gap, VA


Chester Gap Cellars 79 Properties

Frequently Asked Questions About Chester Gap?

What are the top vacation rentals in Chester Gap?

Find the best options in or near Chester Gap for pet-friendly travel. If you are planning a trip or vacation in Chester Gap, 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 Chester Gap:

How many PetFriendly vacation rentals are available in Chester Gap?

PetFriendly™ 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 81 in the Chester Gap 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 Chester Gap.


People Also Ask

There are 81 Chester Gap, VA Vacation Rentals

Recently Booked Pet Friendly Hotels and Vacation Rentals in Chester Gap