Chester Gap Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Brian V. Rowe
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 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
Chester Gap Holiday
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 NZ$195 per night from 24 Nov to 25 Nov
NZ$195
24 Nov - 25 Nov
includes taxes & fees
9.4/10 Exceptional! (1,050 reviews)
Staff was very friendly, room clean and neat.
Reviewed on 14 Nov 2025
Country Inn & Suites by Radisson, Winchester, VA
141 Kernstown Commons Blvd Winchester VA
Fully refundable
The price is NZ$187 per night from 30 Nov to 1 Dec
NZ$187
30 Nov - 1 Dec
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
Very courteous and room was very clean ,swimming pool was very relaxing after long drive!
Reviewed on 18 Nov 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is NZ$142 per night from 21 Dec to 22 Dec
NZ$142
21 Dec - 22 Dec
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
The room was large and well furnished. A good place for a night’s rest. Night manager struck me as more inclined to suspicions about the guest than welcoming. Day manager was most helpful.
Reviewed on 19 Nov 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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
