Name: Comfort Inn & Suites Winchester
Price range: CA $149
Rating: 9.4

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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

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

Fully refundableReserve now, pay when you stay

CA $120

CA $133 total

Jun 14 - Jun 15

includes taxes & fees

8.2/10 Very Good! (1,005 reviews)

"The room smelled like an ashtray"

Reviewed on Jun 11, 2026

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

Fully refundable

CA $149

CA $162 total

Jun 21 - Jun 22

includes taxes & fees

9.4/10 Exceptional! (1,120 reviews)

"Room was spotless and spacious. Breakfast was excellent with everything fresh and in abundance. TV had poor to few selection of premium channels"

Reviewed on Jun 12, 2026

Hillside

1460 US Highway 211 East Luray VA

Fully refundableReserve now, pay when you stay

CA $166

CA $191 total

Jun 16 - Jun 17

includes taxes & fees

9/10 Wonderful! (1,009 reviews)

"Friendly staff"

Reviewed on Jun 8, 2026

See all 517 properties in Chester Gap

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.