79+ Hotel & Resort Deals in Chester Gap |
  1. USA
  2. Virginia
  3. Winchester
  4. Chester Gap

Chester Gap Hotels, Resorts, and Rentals

About Chester Gap Vacation Rentals

There are more than 79 places to stay in Chester Gap that are available. These options include 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 places to stay in Chester Gap.

Are you seeking a last-minute 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 Hotala Chester Gap, you can quickly compare different options to find the hottest deals with a single click. Looking for 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 972.79 ft² on average, with prices averaging US $300 a night.

Hotala 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 reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chester Gap

Type Count
Vacation Homes 31
Cabin Rentals 18
Holiday Apartments 17
B&B 3
Cottages 3
Ski Chalet Rentals 2
Villas 1

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

★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Chester Gap.

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

Stay Near Chester Gap's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Chester Gap's top attractions, neighborhoods, and points of interest.


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 Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Chester Gap Cellars 79 Properties

Frequently Asked Questions About Chester Gap?

What are the top hotels or resorts in Chester Gap?

You have a lot of choices in or near Chester Gap. If you need a hotel in the Chester Gap area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chester Gap:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 79 in the Chester Gap area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chester Gap.


People Also Ask

There are 4 hotels in Chester Gap and 67 rentals

Recently Booked Hotels, Resorts, or Rentals in Chester Gap