Chester Gap Holiday Packages

Save when you book Chester Gap package deals

Choose two or more items and save on your trip:

Top Chester Gap hotels

Modern Mountain Retreat w/ Deck + Hot Tub!

Modern Mountain Retreat w/ Deck + Hot Tub!

Chester Gap
Modern Mountain Retreat w/ Deck + Hot Tub!: Family-friendly holiday home with 1 hot tub and WiFi.
Overall great
"We had a wonderful long weekend at this rental with two families (4 adults, 2 toddlers, and 1 dog). The house was as described—clean, comfortable, and very well-equipped. The kitchen was impressively stocked with everything we needed to cook meals, and we especially appreciated the thoughtful extras ..."

Reviewed on 26 Jun. 2025

Get rates
Modern Mountain Retreat w/ Deck + Hot Tub!
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 17 Aug to 18 Aug
AU$163
17 Aug - 18 Aug
includes taxes & fees
Comfort Inn & Suites Winchester: Pet-friendly hotel with free breakfast and free WiFi. Located in a shopping district.
"Friendly staff. Good location. Lots of places to eat. Within walking distance. Property was clean. And well maintained."

Reviewed on 2 Aug. 2025

Comfort Inn & Suites Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 1 Sept to 2 Sept
AU$121
1 Sept - 2 Sept
includes taxes & fees
Ramada by Wyndham Strasburg/Shenandoah Valley: Pet-friendly hotel with free breakfast and free WiFi. Located in the mountains.
"Very clean. Bed was comfortable."

Reviewed on 3 Aug. 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
Don't see what you're looking for?
See all available properties in Chester Gap
View all properties
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.