82+ Rental Villas and Private Getaways in Chester Gap |
  1. USA
  2. Virginia
  3. Winchester
  4. Chester Gap

Chester Gap Vacation Rentals & One Degree Stays Homes

About Chester Gap Vacation Rentals

There are more than 82 vacation rentals that are available in Chester Gap. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Chester Gap.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Chester Gap, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Chester Gap. Places to stay near Chester Gap are 954.28 ft² on average, with prices averaging US $313 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Chester Gap with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Chester Gap

Type Count
Vacation Homes 32
Holiday Apartments 23
Cottages 3
Villas 1

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

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect 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

OneDegreeStays 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 vacation rentals in Chester Gap?

There are a lot of options in Chester Gap. If you plan on staying in the Chester Gap area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chester Gap:

Which vacation homes in Chester Gap are best for families?

If you are looking for a family-friendly vacation home in Chester Gap, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester Gap:

How many onedegreestays vacation rentals are available in Chester Gap?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 82 in the Chester Gap area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Chester Gap. 


People Also Ask

There are 82 Chester Gap, VA Vacation Rentals

Recently Booked Vacation Rentals in Chester Gap