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Vacation rentals in Chester Gap

Vacation rentals in Chester Gap

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester Gap

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

  • Carson Mountain Cottage
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1 bathroom
    Carson Mountain Cottage

    A mountain retreat...solitude for singles, a romantic getaway for couples... Carson Mountain Cottage is a cozy, self-catering, vacation rental for individuals and couples. Set on a full, wooded acre in the community of Chester Gap in Rappahannock County. The cottage is less than a five minute walk from the Appalachian Trail and Shenandoah National Park. We request a two night stay minimum.

    What guests are saying:

    “This is a great place to stay for a quiet weekend. The cabin is clean and cozy, and the area surrounding the cabin is quiet so you feel very secluded. The Appalachian Trail head is close by, so it was a bonus to be able to hike to Shenandoah NPS without having to drive. Our hike to Compton Peak and back was about 3 and half hours. Also, Front Royal is close by so you can easily drive 10-15 mins to pick up some food (we had take out from Try Thai which was great) I also recommend stopping by Chester Gap Cellars which is down the road five minutes away by car.”

  • Fin de la rue
    SUPERHOSTEntire house · 2 guests · 1 bed · 1 bathroom
    Fin de la rue

    When your adventures are done for the day, come back to relax...sit outside and watch the birds, take a bath, watch a movie, sleep in the new king size bed. The lower half of the house is yours to enjoy, including: separate parking, private entrance, new king size bed, full bath with tub/shower, living area with tv (DVD only), dining table, small kitchen area includes a full-size refrigerator, microwave, and electric kettle.

    What guests are saying:

    “Susan’s place is beautiful, it’s up on a mountain which made for a beautiful view. I only stayed the night but the place was really nice and clean and quiet. The shower was hot and the bed was comfy! I was sort of disappointed the TV was not in the main studio space but a smaller side room. So I didn’t use it. It was a bit colder than I expected but they provided a space heater to warm the space up which worked out perfectly. The homeowners do live upstairs so you will smell the goodness of their cooking and hear footsteps. Otherwise the space is all your own.”

  • So, Shenandoah!
    SUPERHOSTEntire guest suite · 6 guests · 3 beds · 1 bathroom
    So, Shenandoah!

    Enjoy fresh forest air, chill in your own modern cabin-like oasis in the woods, and still utilize WiFi, a full kitchen, and private laundry. Literally just a few minutes away from Shenandoah National Park Entrance / Skyline Drive, grocery, and Front Royal’s Main Street. The pool will be open in May, the perfect way to relax after a nice hike.

    What guests are saying:

    “Leave all of your worries behind. You’ll have everything you need once you arrive at Oh Shenandoah! Izzy and Justin were incredible hosts and will make sure your stay is as pleasant as possible. The space is probably best for two people. You should definitely make time to enjoy the pool if you come in the summer. It’s a zen space for a retreat. You really don’t even need to make plans! The house is a bit tricky to find so get good directions before you arrive. When you turn onto the road the house is on, just keep following the windy uphill narrow road until you pass three houses. The house is on the right past the “cat house” — marked by the cat sign on the left. I would also bring bug spray. It’s not a space for people terrified of nature. I can’t wait to come back. Thank you Izzy and Justin!”

Holiday rentals for every style

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Popular amenities for Chester Gap holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester Gap

Ashby's Perch -- A Very Special Retreat
SUPERHOSTEntire house
Ashby's Perch -- A Very Special Retreat
Price:€243 / night
The Nest
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The Nest
Price:€509 / night
The Cottage
SUPERHOSTEntire cottage
The Cottage
Price:€181 / night
TimberWend
SUPERHOSTEntire cabin
TimberWend
Price:€111 / night
Virginia Mountain Modern Retreat
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Virginia Mountain Modern Retreat
Price:€190 / night
Private Mountain Room
SUPERHOSTPrivate room
Private Mountain Room
Price:€22 / night
Valley Vista, stunning views in wine country
SUPERHOSTEntire house
Valley Vista, stunning views in wine country
Price:€88 / night
Beau Ridge Cabin.
SUPERHOSTEntire cabin
Beau Ridge Cabin.
Price:€110 / night
"Cosy Rose Room" Vineyard Vista Country Getaway
SUPERHOSTPrivate room
"Cosy Rose Room" Vineyard Vista Country Getaway
Price:€53 / night
River Refuge
SUPERHOSTEntire guest suite
River Refuge
Price:€66 / night
Cedar Creek Wayside Castle
SUPERHOSTEntire house
Cedar Creek Wayside Castle
Price:€265 / night
Villa Montaña
SUPERHOSTPrivate room
Villa Montaña
Price:€40 / night
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