Vacation rentals in Chester Gap

Three Meadows Farm, outdoor views, great location

As you approach the driveway on the private lane, you'll be welcomed by beautiful meadows and rolling hills. Set on 10 acres in a shaded, forest of mature trees it's comfortable year round. There are beautiful mountain views from several locations on the property. It's peaceful and quiet here most of the time. We're conveniently located just minutes from Flint Hill, not much farther to Washington VA, Sperryville and Front Royal. It's a two bedroom/one bathroom apartment above a detached garage.

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!

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.

Easy, Private and Peaceful, 2 minutes from I-81

Relax in a quiet private suite right off I-81. It's clean and sanitized following CDC guidelines. A self check-in touch pad lock for ease of entry and exit. Located 2 minutes from historic Woodstock, minutes from wineries, breweries, the Shenandoah River, State and National Forests. Private entrance, yard and parking. Comfortable and cozy queen sized bed, kitchenette, coffee maker, microwave, refrigerator, bathroom and shower with WiFi

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.

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.

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.

Idle Hour at Chester Gap

Whole house in the foothills of the Shenandoah Mountains and the heart of Virginia wine country. The house is adjacent to Chester Gap Cellars, which offers weekend wine tastings, tours, hiking trails, and spectacular views. Access to the Appalachian Trail is nearby along with Shenandoah National Park, Skyline Drive, and the Shenandoah River. House features expansive back deck, outdoor dining, and private hot tub.

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