Photo by Brian V. Rowe

Chester Gap holiday rentals

We found 144 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Chester Gap to find one that's perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a hot tub. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Chester Gap getaway

Learn about the unique charm of Chester Gap with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Chester Gap

Are you looking for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chester Gap a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Linden Vineyards (4 mi / 6.4 km)
  • Naked Mountain Winery & Vineyards (9 mi / 14.5 km)
  • Blue Ridge Shadows Golf Club (9.8 mi / 15.7 km)
  • Little Washington Winery (11.7 mi / 18.9 km)
  • Delaplane Cellars (12.6 mi / 20.2 km)
  • Virginia River Trips (14.2 mi / 22.8 km)

Exploring the natural landscape of Chester Gap

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Chester Gap is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Dickey Ridge Visitor Center (3.9 mi / 6.3 km)
  • Front Royal Entrance Shenandoah National Park (4.6 mi / 7.4 km)
  • Skyline Caverns (5.5 mi / 8.8 km)
  • Shenandoah River (6.9 mi / 11.1 km)
  • State Arboretum of Virginia (14.9 mi / 24 km)
  • Deer Lake (9 mi / 14.5 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Chester Gap?
According to our data, houses are the most popular type of holiday home in Chester Gap. But as you’d expect, everyone’s idea of an epic trip can differ. Stayz has holiday homes in a variety of shapes and sizes, so you’re sure to discover your ideal fit.
How much does it cost to rent a holiday home in Chester Gap?
The average price for a holiday home in Chester Gap can vary based on factors like season, length of stay and property type. Whether you prefer a sprawling house with room for friends and family or a cosy cottage ideal for just you and the kids, just add your dates of travel to see stays with fantastic value.
How much does it cost to rent a beach house in Chester Gap?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside escape. Click on your Chester Gap travel dates to view your options on Stayz. Can’t live without a private pool? Use our filters to choose the amenities and features you want.
Are there pet-friendly holiday homes in Chester Gap?
Pack a squeezy toy and a bone for your canine companion because Chester Gap has four stays that throw out the welcome mat to pets. Let your four-legged pal join in with the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check the “Pets allowed” filter box.
What are popular home amenities in Chester Gap?
When it comes to home amenities that people prefer in Chester Gap, a firepit, a fireplace and a garden are the most popular. With Stayz holiday homes, there are options to match your style and taste, whether you’re on a trip with friends, relatives or even pets.
Are there large group holiday homes in Chester Gap?
Take your pick of three Stayz properties in Chester Gap that can accommodate five or more people. You’ll enjoy all the room and privacy you need to hang out with your favourite people — and nobody else.
Are there holiday homes in Chester Gap that welcome kids?
Chester Gap has four family-friendly holiday homes to pick from. And finding a stay that welcomes children is a cinch with our “Properties good for families” filter. On top of having the entire place to yourselves, you can also look forward to conveniences and perks like multiple bedrooms, kitchens and private pools.
What are the top attractions for families in Chester Gap?
Keeping the kids entertained during your Chester Gap holiday is a cinch with these top family-friendly attractions:

  • Skyline Caverns
  • Shenandoah River State Park
  • Dickey Ridge Visitor Centre

Are there holiday homes with WiFi in Chester Gap?
Whether you want to stay in touch with world events, write a few emails or surf social media, there are two holiday homes with WiFi in Chester Gap. Check the “WiFi” box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Chester Gap?
You can pick from four Stayz holiday homes with air conditioning in Chester Gap giving you that cooling breeze and extra bit of comfort. Simply enter your preferred dates of travel and then use our filters to search for properties with air conditioning.
How old do you have to be to rent a holiday home in Chester Gap?
The minimum age allowed can vary across properties on Stayz, so double-check the rules of the holiday home in Chester Gap you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Chester Gap for?
The amount of time you can rent a Chester Gap holiday home for depends on each property. Simply put in your dates of travel to see available options that offer extended stays. They come with all the things you need to make your extended getaway more enjoyable and comfortable, like kitchens and air conditioning. Some Stayz holiday properties may also offer weekly or monthly discounted prices, so you can hang around longer for less.

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