Chester Gap Holidays
Photo by Brian V. Rowe
- Plan, book, travel with confidence
- Better togetherSave up to S$134 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chester Gap
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 8 Feb to 9 Feb
S$135
8 Feb - 9 Feb
includes taxes & fees
9.4/10 Exceptional! (1,092 reviews)
Clean room
Reviewed on 9 Jan, 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is S$105 per night from 19 Jan to 20 Jan
S$105
19 Jan - 20 Jan
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Breakfast fresh, good coffee, enough healthy variety
Reviewed on 6 Jan, 2026
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is S$116 per night from 25 Jan to 26 Jan
S$116
25 Jan - 26 Jan
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
It was all totally smooth
Reviewed on 7 Jan, 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.
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
