Photo by Brian V. Rowe

Chester Gap vacation rentals

We found 122 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Scroll through and select from vacation rentals in Chester Gap to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. No matter what you're looking for, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Houses

Houses
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect vacation rental for your Chester Gap getaway

Experience the unique character of Chester Gap with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Chester Gap

Are you hoping to find attractions to see in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Chester Gap a fun place to get away. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Glen Manor Vineyards (5.2 mi / 8.3 km)
  • Blue Ridge Shadows Golf Club (9.8 mi / 15.7 km)
  • Little Washington Winery (11.7 mi / 18.9 km)
  • Barrel Oak Winery (12.5 mi / 20.2 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 looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chester Gap. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Shenandoah River State Park (9.1 mi / 14.6 km)
  • Sky Meadows State Park (13.2 mi / 21.2 km)

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chester Gap?

According to our data, houses are the most popular type of vacation rental in Chester Gap. But as you'd expect, everyone's idea of an epic trip can differ. Vrbo has vacation rentals in a variety of shapes and sizes, so you're sure to discover your ideal fit.

How much does it cost to rent a vacation rental in Chester Gap?

The average price for a vacation 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 cozy 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 Vrbo. Can't live without a private pool? Use our filters to choose the amenities and features you want.

Are there pet-friendly vacation rentals 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 vacation rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.

What are popular rental amenities in Chester Gap?

When it comes to rental amenities that people prefer in Chester Gap, a firepit, a fireplace and a garden are the most popular. With Vrbo vacation 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 vacation rentals in Chester Gap?

Take your pick of three Vrbo 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 favorite people — and nobody else.

Are there vacation rentals in Chester Gap that welcome kids?

Chester Gap has four family-friendly vacation 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 vacation is a cinch with these top family-friendly attractions:

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

Are there vacation rentals 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 vacation homes with WiFi in Chester Gap. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

How can I find vacation rentals with air conditioning in Chester Gap?

You can pick from four Vrbo vacation rentals 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 vacation rental in Chester Gap?

The minimum age allowed can vary across properties on Vrbo, so double-check the rules of the vacation home in Chester Gap you're interested in. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Chester Gap for?

The amount of time you can rent a Chester Gap vacation 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 Vrbo vacation properties may also offer weekly or monthly discounted prices, so you can hang around longer for less.