Holiday rentals in Chester Gap

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Top-rated holiday rentals in Chester Gap

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Top guest favourite
The cabin is nestled among tall trees, supported by stilts. Its architecture features a combination of dark siding and wooden beams, with a spacious deck visible, furnished with outdoor seating. Natural greenery surrounds the structure, creating a peaceful atmosphere.
Cabin in Woodstock
5 out of 5 average rating, 126 reviews

The Bird's Nest - Cabin by the River

Located on one of the Seven Bends of the Shenandoah River, the Bird’s Nest is a brand new, custom built 800 square foot cabin featuring an open loft with king bed and skylights, steam shower, heated bathroom floor, and gas fireplace. Exterior amenities include a hot tub, gas grill, gas fire pit table, fire pit by the river, and private river access in a peaceful, wooded setting. Kayaks/tubes are available to use to float down the river with the unique ability to park/exit on the hosts’ property.

Guest favourite
A spacious deck offers unobstructed views of rolling hills and valleys, accented by vibrant autumn foliage. The sky is expansive, displaying soft clouds and blue tones. A sleek railing encircles the deck, enhancing the serenity of the natural landscape.
Cottage in Markham
4.96 out of 5 average rating, 173 reviews

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Top guest favourite
A rustic cabin is illuminated by warm golden light from its windows, set against a soft twilight sky. The log exterior reflects the vintage charm of the structure, while the surrounding trees create a serene atmosphere, inviting guests to relax on the front porch.
Place to stay in Bentonville
4.99 out of 5 average rating, 506 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. An inviting front porch with swing is waiting for you @walnuthillcabin

Top guest favourite
A spacious bedroom features a queen-size bed adorned with decorative pillows. Natural light enters through a skylight and windows. A television is positioned against a wall, accompanied by a combination of vintage and modern furniture pieces, creating a cozy and inviting atmosphere.
Flat in The Plains
4.98 out of 5 average rating, 658 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
The interior of the cabin features natural wood paneling and high ceilings, creating an open and spacious atmosphere. A full-sized bed is dressed in soft linens, complemented by a decorative rug on the polished wooden floor. Light filters in through two windows, enhancing the serene space.
Guest house in Front Royal
4.88 out of 5 average rating, 113 reviews

Cozy Shenandoah River Cabin (10min to Nat’l Park!)

Come get away to our cozy guest cabin, just 10 mins from Shenandoah National Park and a 5 min walk to the Shenandoah River! Perfect for a peaceful stay in a gorgeous natural setting. High ceilings, open concept, wood panelling and a private enclosed patio. Close to vineyards, breweries and outdoor attractions. (Please note, there isn't a full kitchen) If you have more than 3 guests, please let us know. We have a second cabin on the property that we can offer as an additional space.

Top guest favourite
A spacious house is set against a backdrop of rolling hills and deciduous trees, showcasing a blend of natural stone and siding. The property features a well-kept lawn with a pathway leading to the front entrance, providing a welcoming approach to the home.
Home in Front Royal
4.91 out of 5 average rating, 121 reviews

Mountain Retreat Serenity and Quiet in Shenandoah

Our dacha is your escape from clutter and noise of the every day life, offering great mountain views, just 5 minutes away from Front Royal, Luray Caverns, Shenandoah National Park (our 10 acre property borders the Park), and boat access to Shenandoah river. Plan your hikes and day trips and then come back to enjoy the hot tub. Play table tennis inside our air conditioned/heated garage, badminton outside or simply chill and enjoy the views.

Guest favourite
A bright studio space features a queen size bed adorned with white linens. A TV mounted on the wall is visible, along with an air conditioning unit positioned by the window. A compact kitchen area is present, highlighted by a green bar and coffee station. Two chairs and natural light contribute to the inviting ambiance.
Guest house in Maurertown
4.85 out of 5 average rating, 288 reviews

Studio along i81: Near Wine, Beer, Hiking & Nature

Newly renovated detached studio guest-suite located in the beautiful Shenandoah County with country feels and easy access to I81. It features a butcher block bar for eating/working, a queen size bed, tv with Netflix along with Chromecast so you can cast your favorite shows from your phone/laptop, and during the summer you'll have the quietest and smart ac unit on the market. It has a shared driveway with the host's primary residence.

Top guest favourite
The guesthouse's exterior features sturdy stone walls and a green metal roof. White window shutters enhance the classic design. A covered porch provides a welcoming entrance, while lush green grass and neatly trimmed hedges surround the building. Scenic views of the property are visible in the background.
Guest house in Flint Hill
4.97 out of 5 average rating, 152 reviews

Summer kitchen guesthouse at Caledonia Farm 1812

Summer kitchen guesthouse built of stone in 1812 and located on a 115 acre free-range cattle farm on the National Register of Historic Places. The first floor is a living room with the original cooking fireplace and a kitchenette. Upstairs is a loft bedroom and bath. Housekeeping is provided on Monday and Friday mornings. Enjoy the peace and quiet, dark skies, scenic views, adventure, and culinary excellence of Rappahannock County.

Top guest favourite
A table set with checkered linens is surrounded by rustic wooden chairs, situated on a lush green lawn. In the background, a two-story home features a blend of contemporary and rustic design, with prominent windows and a sloped metal roof.
Flat in Marshall
4.94 out of 5 average rating, 179 reviews

The Lodge at Turkey Creek

Take advantage of our special $99 Winter rate‼️ Your low-tech getaway awaits in the heart of the coveted Virginia Piedmont horse & wine country! Nestled in the woods at the end of a half mile private drive you will find quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, charming towns, idyllic scenery, mountains and wineries.

Top guest favourite
Home in Front Royal
4.95 out of 5 average rating, 128 reviews

Shenandoah Getaway | Cozy, Clean & Well-Located

Relax in this cozy, private suite near the Blue Ridge Mountains, Appalachian Trail, historic Front Royal, and the new Warren Memorial Hospital. Tucked in a quiet cul-de-sac, it features a queen bed and full-size floor mattress with fresh linens, fast Wi-Fi, Smart TV, stocked bathroom, and light cooking setup. After a day of hiking or sightseeing, unwind by the fire pit or enjoy a quiet evening on your private patio.

Top guest favourite
A spacious living area features a light-colored sofa positioned on a patterned area rug. Exposed wooden beams grace the ceiling, enhancing the rustic charm. A stone fireplace provides a focal point, while natural light enters through large windows, illuminating the warm interior.
Cabin in Linden
4.97 out of 5 average rating, 229 reviews

Cedarbank • Cabin in Virginia Wine Country

Come visit Virginia wine country and nearby Shenandoah National Park in this modern log cabin. The Cedarbank cabin carries all the conveniences of modern living including updated kitchen and WiFi. Though the grounds are only an hour from Washington DC, Cedarbank feels like a world apart, providing relaxing views and 7 tranquil acres for the perfect rejuvenating country escape. SEE NOTES ABOUT OUR AMENITIES

Top guest favourite
A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.
Cabin in Fort Valley
4.98 out of 5 average rating, 111 reviews

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!

Popular amenities for Chester Gap holiday rentals