Chester Gap Holidays
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Your Chester Gap Holiday
When a city adventure is calling your name, answer it with a Chester Gap holiday package. With all your travel needs taken care of before you leave, all you have to do here is focus on having fun. Want to see the sights but don't know where to begin? Every trip to Chester Gap should include Rappahannock Cellars. Browse Expedia's extensive range of travel options and start organising your perfect holiday to Chester Gap now.
Chester Gap Holiday
Chester Gap Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 840 |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Skyline Caverns, Shenandoah River State Park and Linden Vineyards |
Our pick of the best Chester Gap Hotel Deals
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is AU$158 per night from 25 Mar to 26 Mar
AU$158
25 Mar - 26 Mar
includes taxes & fees
9.4/10 Exceptional! (1,091 reviews)
Great location; easy access off hwy. Very nice staff; clean room; comfortable beds and nice breakfast!
Reviewed on 20 Mar 2026
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 29 Mar to 30 Mar
AU$172
29 Mar - 30 Mar
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
All the staff members were so nice and kind!! The hotel room I booked were very clean and spotless, and the breakfast was even fresh too!
Reviewed on 21 Mar 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 30 Mar to 31 Mar
AU$123
30 Mar - 31 Mar
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Was a nice stay had a great time at the little restaurant
Reviewed on 17 Mar 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.
