Chester Gap Holidays
- 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
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is S$125 per night from 8 Mar to 9 Mar
S$125
8 Mar - 9 Mar
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Very courteous staff - clean hotel, great breakfast.
Reviewed on 23 Feb, 2026
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
The price is S$137 per night from 15 Mar to 16 Mar
S$137
15 Mar - 16 Mar
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Great one night stay! Friendly, welcoming staff! Room was clean and comfortable. Location was perfect- near dining and highway!
Reviewed on 27 Feb, 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is S$108 per night from 13 Mar to 14 Mar
S$108
13 Mar - 14 Mar
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
We couldn’t find out tooth brushes and I called the front desk and had them as well as tooth paste delivered with a smile to our room within 10 minutes. We’ve stayed her on our way to Georgia for about 9 years now and we’ve never been disappointed. 😊
Reviewed on 26 Feb, 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.
