Vacation rentals in Chester Gap

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester Gap

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

Home in Chester Gap

Modern Mountain Retreat w/ Deck + Hot Tub!

Pack your bags for an unforgettable getaway to the Shenandoah Mountains at this newly renovated Chester Gap vacation rental! This 3-bedroom, 2.5-bath home features mid-century modern rustic decor, high-end appliances, and a private outdoor space complete with an expansive deck, hot tub, fire pits, and an abundance of outdoor games! When you're not enjoying all the comforts of this home, sample wines at a local vineyard, visit historic sites, or hike the Appalachian Trail just out your front door!

$202 per night

Cottage in Markham

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!

$250 per night

SUPERHOST

Home in Front Royal

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.

$308 per night

SUPERHOST