Holiday rentals in Chester Gap

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester Gap

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cabin in Front Royal

4.99 out of 5 average rating, 188 reviews

Valley View Cabin

The coziest little cabin to getaway from the hustle and bustle of the city, but only an hour away from Washington DC. Our hope is you enjoy every part of your stay at this little cabin; from enjoying your morning cup of coffee on the screened in porch while watching deer or turkey graze in the yard, or venturing to the quaint Main Street of Front Royal. This town has so much to offer. Only 15 minutes away from Shenandoah National Forest & skyline drive. A perfect place for kayaking & canoeing!

Guest favourite

Guest house in Marshall

5.0 out of 5 average rating, 103 reviews

Moon Hold Cottage - Retreat, Refresh, Recharge

Unplug from city life and venture out to our small organic farm. Spend a night or two in the private guest cottage while enjoying nearby vineyards and restaurants. Spend the day browsing in the local antique shops or relax on the farm and watch nature's display (butterflies, birds, an occasional critter.) We may be working in the garden or putting up hay. We're always glad to share a bit of the harvest when the vegetables are ripe, so you can take some home to enjoy. All are welcome here!

Guest favourite

Home in Edinburg

4.98 out of 5 average rating, 360 reviews

Jay Birds Nest - Pet Friendly

Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

Guest favourite

Place to stay in Bentonville

4.98 out of 5 average rating, 390 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. A large front porch with swing is waiting for you. @walnuthillcabin

Guest favourite

Flat in The Plains

4.98 out of 5 average rating, 451 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Guest favourite

Campsite in Front Royal

4.99 out of 5 average rating, 109 reviews

Blue Mountain Hideaway Boutique Camping Experience

Escape to a truly unique camping experience at our creek-side retreat. This park-like paradise is perfect for hassle free camping, all you need to bring your cooler and clothes. We provide everything else! Take advantage of heavily discounted off season rates! Throughout the winter season we will be opening our calendar two weeks in advance, weather dependent to ensure that our off grid water does not freeze. A propane heater is provided to ensure your sleep space is warm and toasty.

Guest favourite

Cottage in Warrenton

4.97 out of 5 average rating, 264 reviews

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Guest favourite

Farm stay in Warrenton

4.98 out of 5 average rating, 528 reviews

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this private cottage. Watch for deer, turkeys and maybe even a bear in the field from the sun room, or take a hike around the homestead. Centered in Fauquier's wine country it is ideal for the weekend escape, and day trips West to the mountains, East to DC or points south. Perfect for those extra reunion family members, wedding guest accommodations, or the "Hafeway overnighter" traveling North or South.

Guest favourite

Chalet in Front Royal

4.96 out of 5 average rating, 180 reviews

Bear Mountain Lodge

Bear Mountain Lodge is in the Shenandoah mountains, less than 10 minutes to the Skyline Drive - Front Royal entrance. Enjoy hiking trails, the Shenandoah River, wineries, and all of what Front Royal has to offer. Secluded property offers privacy and peace and quiet. Wifi, Cable TV, toilet paper, paper towels, shower towels, pillows, and sheets are provided. Hot Tub! Both Kuerig and drip coffee machines available. Everyday kitchen essentials included.

Guest favourite

Cabin in Front Royal

4.98 out of 5 average rating, 103 reviews

Luxury Lodge Fire Pit, Hot Tub, & Sauna

Welcome to Wildflower Lodge, your luxury getaway nestled on 3 acres, just 5 minutes from Shenandoah National Park and Skyline Drive. An hour and a half from Washington DC, our modern lodge is perfect for family and friends. Enjoy a fully enclosed backyard and explore local wineries, breweries, and Shenandoah Valley's outdoor attractions. Offering comfort and adventure, it's the ideal spot for those seeking to relax or explore the great outdoors!

Guest favourite

Flat in Bentonville

4.98 out of 5 average rating, 239 reviews

Full Circle Farm Shenandoah Valley No Cleaning Fee

Stay in beautiful Bentonville VA. At the foot of skyline drive and minutes from award winning wineries; near Luray Caverns and the Shenandoah River where you can canoe, raft or kayak. You’ll be on our private property and have complete privacy up the hill from our home. Full kitchen/washer/dryer/TV and WiFi. Explore and enjoy the mountains, river, trails and wine. Pets are welcome. A fee is calculated per pet. $25 per pet. NO CLEANING FEE!

Guest favourite

Guest house in Warrenton

4.98 out of 5 average rating, 256 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.