
Vacation rentals in Chester Gap
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Top-rated vacation rentals in Chester Gap
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Chapel View Nest: Patio, Firepit and Views.
Stay in our secluded getaway on 20 acres with skyline mountain views and stunning sunsets. The main house is perched atop a hill with the English basement attached. Guests will have their own private sunny patio with a gas fire pit and grill. Relax and unwind in this welcoming tucked away spot that is private and tastefully furnished with everything you need for a wonderful stay. Nearby: Christendom College ~1 m Warren Memorial Hospital 2.5 m Shenandoah Park Skyline Dr. 6 m Front Royal 6 m

Valley View Cabin /10 min from National Park entry
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!

Cozy Reliance Retreat with Beautiful Views
Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps two and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

Shenandoah Mountain House (Guest Suite)
Smells of the forest. Sights of the mountain. Conveniences of home. Welcome to our little secret in Shenandoah! Our chalet is situated on the hills surrounding Shenandoah Valley. Walk 25 minutes to the river. Drive 10 minutes to the national park entrance and Skyline Drive. Roads are in excellent condition year-round. Your guest suite is on the ground floor, recently finished, with a private entrance (separate from the main house), with access to outdoor space, deck, swings, fire pit etc.

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

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.

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.

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.

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.

The Lodge at Turkey Creek
Take advantage of our special $99 Winter rate for Jan-Feb. 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.

COZY River Cabin + HOT TUB + Swanky, Sexy, FUN!
Have fun at Starlight on the River! Chill vibe with high style and sexy romance! ***Hot tub and river views*** Pop meets mid-mod design, modern cabin meets urban flare! The most perfect one bedroom, hot tub, riverfront Airbnb you will find, only 60 minutes from Washington DC! From life size tigers to real eagles flying by, Starlight will be a memory to never forget! ~Treat Yourself to Starlight, You Deserve This! ~

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.
Popular amenities for Chester Gap vacation rentals
Other great vacation rentals in Chester Gap

The Cottage at the Barb Farm

Screened Porch w/Swing, Fire Pit, Grill & Deck

New! Zen Cabin in the Clouds

The Grape Escape - A-Frame Cabin in Wine Country

Monthly only one-bedroom private efficiency

Modern Mountain Retreat w/ Deck + Hot Tub!

NEW Hike Wine & Dine! Shenandoah NP & Top Wineries

Three Meadows Farm, outdoor views, great location
Destinations to explore
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- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Stone Tower Winery
- Early Mountain Winery
- Great Falls Park
- Cacapon Resort State Park
- Prince Michel Winery
- Tysons Corner Center
- Harpers Ferry National Historical Park
- Jiffy Lube Live
- Shenandoah River Outfitters
- George Mason University
- Sky Meadows State Park
- Big Cork Vineyards
- James Madison University
- Cooter's Place
- White Lotus Eco Spa Retreat
- Bluemont Vineyard
- Antietam National Battlefield
- Reston Town Center
- EagleBank Arena
- Museum of the Shenandoah Valley
- Old Town Winchester Walking Mall




