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Vacation rentals in Chester Gap

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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!
$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
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

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Cabin in Front Royal
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Liberty Hall Cabin - Family Retreat with a View!
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Chapel View Nest: Patio, Firepit and Views.
$124 per night
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The CannaBus
$80 per night
Chalet in Front Royal
Bear Mountain Lodge
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Home in Front Royal
Cozy house in Shenandoah N.P. City of Front Royal
$108 per night
Cabin in Linden
Deer Haven | Blue Mountain Retreat w/ Hot Tub
$176 per night
Guesthouse in Front Royal
The Loft at Pine Haven
$114 per night
Rental unit in Front Royal
NEW! Cozy 1 Bedroom Loft
$131 per night

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