Chester Gap Vacation Packages
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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
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from May 3 to May 4
CA $117
CA $130 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The hotel and room were okay, and the breakfast was good. However, I was disappointed to find a large stain on my sheets that I didn’t notice until the morning. As far as the checkout experience. I waited about 15 minutes for someone to come to the front desk, but no one showed up. While I was standing ...
Reviewed on Apr 27, 2026
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is CA $142 per night from May 25 to May 26
CA $142
CA $155 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,108 reviews)
Staff and property was great
Reviewed on Apr 29, 2026
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from May 17 to May 18
CA $150
CA $167 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
Wonderful hotel and stay. Would recommend to anyone.
Reviewed on Apr 27, 2026
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.
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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.
