Chester Gap Holidays
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Top hotels in Chester Gap
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 7 Jul to 8 Jul
S$121
7 Jul - 8 Jul
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"Not impressed. Some weird stains on the mattress cover and beside the bed. Sheets were clean. Bed was comfy. Dirty sink. Stained shower curtain and bedspread. Checking in, staff was great. Day staff was not nice and barely spoke. Lady running breakfast was very rude when someone told her the coffee ..."
Reviewed on 27 Jun, 2026
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is S$142 per night from 23 Jul to 24 Jul
S$142
23 Jul - 24 Jul
includes taxes & fees
9.4/10 Exceptional! (1,121 reviews)
"The place was nice, clean and the staff was very friendly and helpful! We booked while travelling and on the website it looked like there was a pool, so we were disappointed to find no pool. Unfortunately it was hard to tell from the confusing technological hoops with the booking apps what the amenities ..."
Reviewed on 29 Jun, 2026
Hillside
1460 US Highway 211 East Luray VA
Fully refundableReserve now, pay when you stay
The price is S$163 per night from 8 Jul to 9 Jul
S$163
8 Jul - 9 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Hillside was a lovely accommodation with a great, convenient location for Skyline Drive hiking. The room was clean with nice amenities. It felt like a home away from home!"
Reviewed on 25 Jun, 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. 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.
