79+ Private Villas and Holiday Rentals in Chester Gap |
  1. USA
  2. Virginia
  3. Winchester
  4. Chester Gap

Chester Gap Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chester Gap

Discover more than 79 vacation rentals available in Chester Gap. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chester Gap.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chester Gap, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chester Gap. On average, places to stay near Chester Gap offer 972.79 ft², with nightly prices averaging CA $414.

With Casai, finding and comparing holiday rentals in Chester Gap is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Chester Gap

Type Count
Vacation Homes 31
Holiday Apartments 17
Cottages 3
Villas 1

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

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation 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

Top Attractions Around Chester Gap, VA

Casai offers a large selection of top attractions around Chester Gap . Research things to do on your vacation before you visit Chester Gap.


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 holiday rentals in Chester Gap?

With numerous options available in Chester Gap, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chester Gap:

Which holiday homes in Chester Gap are best for families?

If you're searching for a family-friendly holiday home in Chester Gap, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chester Gap:

How many Casai.ca holiday rentals are available in Chester Gap?

As of 2025, Casai boasts over 79 properties listed in the Chester Gap area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chester Gap.


People Also Ask

There are 79 Chester Gap, VA Holiday Rentals

Recently Booked Holiday Rentals in Chester Gap