
Chester Gap Vacations
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Your Chester Gap Vacation
Our vacation packages to Chester Gap let you customize your own adventure. Tailor your getaway to suit your interests and needs and make every moment count in this interesting city. Hoping to sightsee? Spend your days enjoying major attractions like Rappahannock Cellars during your trip to Chester Gap. A couple of quick clicks is all it takes to create a customized Chester Gap vacation on Expedia.
Chester Gap Hotel Deals

Modern Mountain Retreat w/ Deck + Hot Tub!
Chester Gap
9.8/10 Exceptional! (57 reviews)
Wonderful home-quiet yet convenient!
"My husband and I stayed in this home for our annual anniversary trip. We love hiking and brought our dog with us for some active relaxation. This home was one of the best we have stayed in. It had everything we needed, and was clean and comfortable. Conveniently located about 15 minutes from Front ..."
Reviewed on May 13, 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Jul 13 to Jul 14
$79 total
Jul 13 - Jul 14
Total includes taxes and fees
8/10 Very Good! (1,008 reviews)
"Very nice hotel!"
Reviewed on Jun 29, 2025

Comfort Inn & Suites
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $105 total per night from Jul 13 to Jul 14
$105 total
Jul 13 - Jul 14
Total includes taxes and fees
9.4/10 Exceptional! (1,003 reviews)
"Clean, quiet, friendly and helpful staff."
Reviewed on Jun 27, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Chester Gap Vacation Packages
Chester Gap Essential Information
Language | English |
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Currency | U.S dollars |
Population | 840 |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.