Chester Gap Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Brian V. Rowe
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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 refundableReserve now, pay when you stay
The price is AU$172 per night from 2 Nov to 3 Nov
AU$172
2 Nov - 3 Nov
includes taxes & fees
9.4/10 Exceptional! (1,019 reviews)
"The breakfast was good and a quiet place to stay"
Reviewed on 13 Oct 2025
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd, Winchester, VA
Fully refundable
The price is AU$152 per night from 9 Nov to 10 Nov
AU$152
9 Nov - 10 Nov
includes taxes & fees
8.6/10 Excellent! (1,016 reviews)
"One night stay for a baseball tournament. Room was good and clean. The indoor Pool was good size but was cold."
Reviewed on 12 Oct 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 27 Oct to 28 Oct
AU$138
27 Oct - 28 Oct
includes taxes & fees
8.2/10 Very Good! (1,014 reviews)
"The property was easy on and off Rt81. Staff was friendly and helpful. Rooms were clean and the restaurant attached was excellent."
Reviewed on 9 Oct 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
