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Vacation Rentals in Chester Gap

Find the vacation rentals that appeal to you the most

August 2026

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The best vacation rentals in Chester Gap

Check out our selection of great vacation rentals in Chester Gap

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Mountain Home Bed & Breakfast

Front Royal (Near Chester Gap)

Mountain Home Bed & Breakfast in Front Royal provides accommodations with a garden and a tennis court. With mountain views, this accommodation provides a patio.

T
Theda
From
United States
The breakfast was excellent. Scott's pear cider and jam were both delicious. We enjoyed talking to both Lisa and Scott. They were charming. I am recommending this B&B to our daughter and son-in-law.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 195 reviews
Price from
$164
1 night, 2 adults

1 min walk to The Inn-Entire Colonial 3BR House with tub & Fast WiFi

Washington, Virginia (Near Chester Gap)

1 min walk to The Inn-Entire Colonial 3BR House with tub & Fast WiFi offers accommodations in Washington, Virginia, 6.1 miles from Haley Fine Art and 10 miles from Gray Ghost Vineyards.

D
Daniel
From
United States
Great value; incredible location and marvelous owners. Thoroughly enjoyed the experience!!!
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 13 reviews
Price from
$227.05
1 night, 2 adults

Gay Street Inn

Washington, Virginia (Near Chester Gap)

Gay Street Inn enjoys a location in Washington, Virginia, 17 miles from Pinnacles Viewpoint and 19 miles from Crosby Stadium.

B
Brent
From
United States
Attentive hosts, they seem to care a lot about your experience , calling ahead to make sure your check in goes smooth, and that you enjoyed your stay.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 6 reviews
Price from
$359
1 night, 2 adults

Shenandoah mountain cottage w hot tub & fire pit

Front Royal (Near Chester Gap)

Shenandoah mountain cottage w hot tub & fire pit is located in Front Royal, just 11 miles from Crosby Stadium and 11 miles from Historic Long Branch.

c
chet
From
United States
Great location. Nice and quiet. It was the perfect cozy little cottage.
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 9 reviews
Price from
$241.01
1 night, 2 adults

Log cabin w riverfront & hot tub

Rileyville (Near Chester Gap)

Log cabin w riverfront & hot tub offers accommodations in Rileyville, 13 miles from Luray Caverns and 15 miles from Crosby Stadium.

J
John
From
United States
Cabin and location were excellent
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 8 reviews
Price from
$348.98
1 night, 2 adults

Marriott Ranch Bed and Breakfast

Hume (Near Chester Gap)

Providing mountain views, Marriott Ranch Bed and Breakfast in Hume offers accommodations, a terrace, and a shared lounge.

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 76 reviews

Chic Front Royal Retreat Near Shenandoah River!

Front Royal (Near Chester Gap)

Chic Front Royal Retreat Near Shenandoah River! offers accommodations in Front Royal, 1.9 miles from Crosby Stadium and 14 miles from Cedar Creek And Belle Grove National Historical Park.

J
Jocelyn
From
United States
We loved the location to the park. The decorations, the layout. We could tell the owner really cares about the place and put a lot of thought into making it cozy. Would definitely stay here again.
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 5 reviews

LeFay Cottage at Little Washington

Washington, Virginia (Near Chester Gap)

Featuring a garden, LeFay Cottage at Little Washington features accommodations in Washington, Virginia. This country house provides air-conditioned accommodations with a patio.

L
Leo
From
United States
It’s lovely and quiet, with marvelous views of the Blue Ridge. It’s close to the main road yet feels secluded, and the extensive lawn and garden give a sense of open privacy. The kitchen is well provisioned with thoughtful touches like half and half cream for tea or coffee. The beds are very comfortable, and the towels super plush. Its location near Little Washington, Sperryville and Flint Hill ensures great dining options. Also close to Shenandoah National Park for pleasant walks.
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 14 reviews

Waterfront Virginia Retreat w/ Canoe, Pets Welcome

Rileyville (Near Chester Gap)

Waterfront Virginia Retreat w/ Canoe, Pets Welcome is located in Rileyville, just 17 miles from Crosby Stadium and 18 miles from Pinnacles Viewpoint.

H
Heavner
From
United States
I loved everything about this little place! It was very clean and very cozy. The location is perfect and the property it's on is very nice. I love the back deck with the bar looking out over the pond. I've been in a lot of rental stays over the years and this is definitely one of my favorites so far. Sarah, our host, made me feel very comfortable and she was very prompt about answering any questions I had. I would definitely recommend this place to anyone!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 5 reviews
All vacation rentals in Chester Gap

Most booked vacation rentals in Chester Gap and surrounding area in the past month

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Popular with guests booking vacation rentals in Front Royal

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 195 reviews

Popular with guests booking vacation rentals in Front Royal

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 5 reviews