85+ Luxury Vacation Rentals & Cabins in Chester Gap |
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  2. Virginia
  3. Winchester
  4. Chester Gap

Chester Gap Cabin Rentals

About Chester Gap Vacation Rentals

There are more than 85 incredible getaway rentals that are available in Chester Gap. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Chester Gap.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Chester Gap, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Chester Gap. Places to stay near Chester Gap are 958.09 ft² on average, with prices averaging US $315 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Chester Gap. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Chester Gap

Type Count
Vacation Homes 36
Holiday Apartments 18
Cabin Rentals 18
B&B 3
Cottages 3
Ski Chalet Rentals 3
Villas 1

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

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Chester Gap with Cabinns.com.

Weather in Chester Gap, VA

View the weather forecast for Chester Gap before booking your Chester Gap Vacation Rentals to confirm your best time to go.

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

Activities Chester Gap Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Chester Gap. Discover Top Attractions For Your Next Outdoor Adventure.


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

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Chester Gap Cellars 79 Properties

Frequently Asked Questions About Chester Gap?

What are the top cabins, lake houses & summer homes in Chester Gap?

We provide an array of great vacation destinations in Chester Gap. If you are looking to stay in or around the Chester Gap area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chester Gap:

Which cabin rental, resort, or holiday home in Chester Gap is best for families?

Searching for a family-friendly cabin in Chester Gap? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Chester Gap?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 85 in the Chester Gap area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Chester Gap.


People Also Ask

There are 3 hotels in Chester Gap and 73 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Chester Gap