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.

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Chester Gap Hotel Deals

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is CA $146 per night from May 4 to May 5
CA $146
CA $159 total
May 4 - May 5
includes taxes & fees
9.4/10 Exceptional! (1,103 reviews)
Parking was convenient.

Reviewed on Apr 11, 2026

Comfort Inn & Suites Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from May 3 to May 4
CA $115
CA $128 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
All good

Reviewed on Apr 13, 2026

Ramada by Wyndham Strasburg/Shenandoah Valley
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Apr 27 to Apr 28
CA $162
CA $181 total
Apr 27 - Apr 28
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Staff couldn’t be more pleasant, hotel updated,breakfast, coffee was a great self serve. Hotel was a stone throw from Shenandoah National park!

Reviewed on Apr 10, 2026

Hampton Inn Front Royal
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.