Photo by Brian V. Rowe

Chester Gap holiday rentals

We found 150 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.

Holiday rentals with weekly discounts – Chester Gap

Showing deals for:13 Nov - 20 Nov

Private kitchen
Dining
Living area
Property grounds
Exceptional
(18 reviews)

Cozy Mountain Cabin with Stunning Views, Modern Comforts & Fast WiFi

Bentonville

8% off
AU$2,134
for 7 nights, 1 cabin
AU$305 per night
includes taxes & fees
Cozy Mountain Cabin with Stunning Views, Modern Comforts & Fast WiFi
Private kitchen
Exterior
Living area
Interior
Exceptional
(20 reviews)

Waterfront Retreat on the Shenandoah River 7 miles from National Park

Front Royal

8% off
AU$4,083
for 7 nights, 1 home
AU$583 per night
includes taxes & fees
Waterfront Retreat on the Shenandoah River 7 miles from National Park
Vaulted-ceiling living room with valley views from wall of windows
Hot tub on private deck at sunset over the Shenandoah Valley
Bright kitchen with white cabinets, island seating, and dining nook
Open kitchen and dining flowing to porch with valley access
Exceptional
(15 reviews)

Apple Mountain House | Hot Tub | Game Room

Front Royal

19% off
AU$3,011
for 7 nights, 1 cottage
AU$430 per night
includes taxes & fees
Apple Mountain House | Hot Tub | Game Room
Living area
Living area
Private kitchen
Interior
Exceptional
(36 reviews)

Shenandoah Escape Cabin - Hot Tub, Sauna, Fire Pit & Forest Views. Near Hiking

Bentonville

8% off
AU$3,412
for 7 nights, 1 cabin
AU$487 per night
includes taxes & fees
Shenandoah Escape Cabin - Hot Tub, Sauna, Fire Pit & Forest Views. Near Hiking
Open-plan kitchen, dining, and living with wall-of-windows valley view
Covered deck with fire pit, string lights, and sweeping sunset views
Open great room with stone fireplace, vaulted ceiling, and valley views
Kitchen island seats four with French-door access to the deck
Wonderful
(9 reviews)

Prima Mountain Cabin | Hot Tub | Game Room

Front Royal

19% off
AU$3,011
for 7 nights, 1 cabin
AU$430 per night
includes taxes & fees
Prima Mountain Cabin | Hot Tub | Game Room
Property grounds
Property grounds
Exterior
Dining
Exceptional
(27 reviews)

Apple Mountain Retreat

Linden

12% off
AU$1,842
for 7 nights, 1 apartment
AU$263 per night
includes taxes & fees
Apple Mountain Retreat
Kitchen sink and prep area with modern stone backsplash
Sunset firepit and rocking chairs above the valley
Formal dining table seating 8 with chandelier and valley view
Open-concept dining and living with mountain views beyond
Exceptional
(23 reviews)

The VUE | Mountaintop 4BR | Hot Tub & Views

Front Royal

12% off
AU$3,988
for 7 nights, 1 cottage
AU$570 per night
includes taxes & fees
The VUE | Mountaintop 4BR | Hot Tub & Views

  • 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, 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)
  • Little Washington Winery (11.7 mi / 18.9 km)
  • Barrel Oak Winery (12.5 mi / 20.2 km)
  • Dinosaur Land (14.3 mi / 23 km)
  • Rappahannock Cellars (1.8 mi / 2.8 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:

  • Shenandoah National Park (28.3 mi / 45.6 km)
  • 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)
  • Lake Frederick Boat Launch (13.1 mi / 21.1 km)

Frequently asked questions

What is the most popular type of holiday rental accomodation in Chester Gap?
In Chester Gap, holiday houses and cottages are the most popular types of holiday rental accommodations, with several options available throughout the area. These properties typically offer spacious living areas, fully equipped kitchens, and outdoor spaces where guests can enjoy the serene views of the surrounding countryside. Many of these rentals are situated in tranquil locations, making them ideal for families or groups seeking a peaceful getaway in the heart of Virginia's natural beauty.
Are there any family house rentals in Chester Gap?
In Chester Gap, Virginia, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features a mix of properties that offer spacious living arrangements, fully equipped kitchens for preparing family meals, and outdoor spaces superb for play and relaxation. Many homes come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all.Visitors can explore the nearby Shenandoah National Park, which offers stunning natural beauty and numerous hiking trails suitable for families. Additionally, the charming town atmosphere in Chester Gap provides a peaceful retreat with opportunities to discover local shops and eateries.
Are there pet-friendly house rentals in Chester Gap?
In Chester Gap, there are several pet-friendly house rentals available, making it an excellent choice for travellers wishing to bring their furry companions along. These rentals typically offer a range of amenities, such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. Many properties feature private yards or patios, providing a secure environment for pets to roam freely.The area is surrounded by beautiful countryside, ideal for outdoor activities with your pet, including hiking and exploring the nearby Shenandoah National Park. The park offers a variety of trails suitable for all skill levels, which can be a delightful experience for both you and your pet.
Are there any remote work holiday rentals in Chester Gap?
In Chester Gap, Virginia, there are several holiday rentals suitable for remote work. Many of these properties come equipped with high-speed internet and additional amenities like Wi-Fi, ensuring a reliable connection for those who need to work from home. Some rentals also offer dedicated office spaces or bookable units with printers, catering specifically to remote workers.The area is known for its serene surroundings and proximity to the beautiful Blue Ridge Mountains, providing a superb backdrop for a productive yet relaxing stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chester Gap?
In Chester Gap, popular holiday rental amenities include inviting features that enhance the comfort and enjoyment of guests. Many properties come equipped with a fireplace, superb for cosy evenings after a day of exploring the beautiful surroundings. Kitchens are common, allowing travellers to prepare their own meals and enjoy dining in the comfort of their rental. For those travelling with pets, it's worth noting that many rentals in the area are pet-friendly, making it easier for guests to bring their furry companions along. Additionally, rentals often include a selection of books for leisurely reading and decks or patios where guests can relax and take in the serene views of the Virginia countryside.
When is the best time to visit Chester Gap for a holiday rental?
April marks the beginning of the peak season in Chester Gap, where visitors flock to experience the stunning beauty of spring. This month is particularly popular as the area awakens with vibrant blooms, making it an ideal time for outdoor activities such as hiking and exploring the picturesque landscapes of the Blue Ridge Mountains.From April to June, Chester Gap buzzes with tourists eager to soak in the lush scenery and partake in various adventures. The mild temperatures, typically ranging from 10 to 20 degrees Celsius, create a comfortable environment for sightseeing and recreational pursuits. Whether you're hiking the Appalachian Trail or enjoying a leisurely picnic in one of the local parks, this season offers ample opportunities to connect with nature.For those seeking a more economical visit, consider planning your trip in November. This month, while quieter, presents a unique opportunity to enjoy the stunning autumn foliage without the crowds, allowing for peaceful exploration and scenic drives through the changing landscapes.Ultimately, choosing the right time to visit Chester Gap depends on your preference for vibrant spring activities or the tranquil beauty of the fall.
What are the top attractions in Chester Gap?
In Chester Gap, Virginia, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Shenandoah National Park is a major draw, offering stunning views, hiking trails, and opportunities for wildlife viewing. The park's Skyline Drive is particularly popular for its scenic overlooks and vibrant fall foliage.For those interested in local history, the charming town of Front Royal, just a short drive away, features attractions such as the Warren Heritage Society and the historic Belle Boyd House. Additionally, Chester Gap is surrounded by wineries and vineyards, allowing for delightful wine-tasting experiences and picturesque landscapes that are great for leisurely afternoons.Outdoor enthusiasts can also explore the nearby Appalachian Trail, which provides ample opportunities for hiking and enjoying the serene natural environment.
Are all fees included in the Chester Gap holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chester Gap holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chester Gap with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chester Gap holiday homes?
You can find great discounts on holiday homes in Chester Gap on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chester Gap holiday home booking on Stayz?
To find Chester Gap holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chester Gap?
A long-stay holiday home in Chester Gap is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chester Gap holiday home?
Book your Chester Gap holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chester Gap?
Prices for holiday homes in Chester Gap vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chester Gap to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.