Vacation rentals in Chester Gap

Mountaintop Retreat with Wood Fired Hot Tub

Named Virginia’s most wishlisted Airbnb, Doah House is an architect-designed retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. Featured in Dwell and Travel + Leisure, the cabin is a container for rest and observation. The stay is shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing light, air, and sound. Each day feels different. The forest changes, and you might, too.

Value · Family · Indoor spaces

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!

Value · Location · Layout

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.

Location · Family · Indoor spaces

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

Family · Value · Cleanliness

Hidden Gem on Hidden Valley Lane

Full relax at this unique and tranquil getaway. Cute cabin in a park like setting with a wood burning fire place. A pond and lake view(mostly 3 seasons of the year). There is a hammock and a rope swing to enjoy. Trampoline for the kids. Starlink internet!!! Hike to a natural spring and a small creek that feeds Rappahanock river. Go fishing, hike the Appalachian trails near by or enjoy the list of local wineries. Front Royal is only 15 minutes away as well as Skyline Caverns and Skyline drive.

Value · Location · Parks

John Pope Cabin Browntown Va. We now have Starlink

Welcome to John Pope Cabin Nestled in foothills of the Appalachian Mountains, John Pope Cabin overlooks an open field where hawks hunt, bears sometimes stroll, and our neighbors’ horses peer over the fence. Feel free to pet them but don’t feed them! Built in 1865 by a Confederate soldier returning from the Civil War birthed and raised 11 children here. The cabin remains rustic, comfortable, and full of character. Ahh…the porch. Relax in the swing, watch the fields change with the light.

Value · Location · Grill

The Cottage

Need some time to refresh? Spending time in the foothills of the Skyline Drive at our cozy cottage may be for you. Well behaved dogs are welcome but not on furniture. The driveway is long and home is very secluded. Winter access will be subject to weather conditions. Driveway does not get plowed and gets rutty during rainy periods. Cell service is spotty on Browntown road. The cottage has a landline and wifi. Use your wifi calling feature for cell phone use. More info under photos.

Location · Value · Parks

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Family · Location · Wifi

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.

Family · Location · Hiking

3br/1ba house up to 6 people

Location and value is what you will get. A level up from Glamping. Minutes drive to Shenandoah National Park. Walking to the shops on Main Street and Martin’s grocery store. You will have the house to yourself. Disclaimer: House is old and has holes bugs can come in. Plumbing is old as well. Please take care of the house like you would take care of Grandma (assuming you’ve never had beef with Grandma). Driveway allows 3 cars.

Value · Family · Decor

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.

Value · Family · Amenities

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!

Location · Family · Parks