Vacation rentals in Chester Gap

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Top-rated vacation rentals in Chester Gap

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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!

$204 per night

Chalet in Chester Gap

NEW Hike Wine & Dine! Shenandoah NP & Top Wineries

Nestled among the rolling hills of the Shenandoah Valley, our chic abode is a nature lover's paradise. Towering, mature trees surround you as you stroll just 0.7 miles to the Appalachian Trail. At only a 10 min drive, we are also the perfect gateway for those looking to explore the beauty of Shenandoah National Park. AND if you're craving some grape-based goodness, some of the region's best wineries are just a hop, skip, and a sip away with 2 Washingtonian recognized wineries within 10 mins!

$244 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.

$303 per night

SUPERHOST