Chester Gap

Travel Guide

Two butterflies on purple flowers.
A field of pink and yellow flowers with a butterfly on one of the pink flowers.
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
The price is CA $108 per night from Nov 1 to Nov 2
CA $108
CA $120 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very good! (1,025 reviews)
"bugs and mold in the room would not recommend"

Reviewed on Oct 13, 2026

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

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
The price is CA $143 per night from Nov 5 to Nov 6
CA $143
CA $159 total
Nov 5 - Nov 6
includes taxes & fees
Book a stay at this golf hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
9.4/10 Exceptional! (1,133 reviews)
"It’s in a very nice shopping plaza next to a grocery store restaurant in movie theater, so it was perfect for me. It’s been relatively recently renovated, but besides that it was very very clean and the staff was excellent from front desk to the night audit and even the woman who did breakfast was ..."

Reviewed on Oct 10, 2026

Comfort Inn & Suites Winchester
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
The price is CA $126 per night from Nov 8 to Nov 9
CA $126
CA $140 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,004 reviews)
"Good location. Easy to find."

Reviewed on Oct 12, 2026

Country Inn & Suites by Radisson, Winchester, VA
See all 542 properties in Chester Gap
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.
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...
10/10 Exceptional! (382 reviews)
"Wonderfully quiet and serene. Super clean. Derek was very accommodating when I realized at the last minute that linens/towels aren't provided unless requested—he had a family member drop them by that night. Firepit and hot tub on the front porch are huge pluses. It was so peaceful that we stayed ..."

Reviewed on Sep 30, 2026

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Front Royal VA
Stay at this vacation home in Front Royal. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shenandoah River and Bing Crosby Stadium are ...
10/10 Exceptional! (45 reviews)
"Great place to stay"

Reviewed on Oct 11, 2026

Mountain View Bungalow in Front Royal
Adorable river front cabin ,with hot tub on the River

Adorable river front cabin ,with hot tub on the River

Luray VA
Stay at this cabin in Luray. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Chalybeate Spring and Fort Valley Public ...
9.2/10 Wonderful! (27 reviews)
"loved the hot tub and the river"

Reviewed on Sep 24, 2026

Adorable river front cabin ,with hot tub on the River
See all properties in Chester Gap
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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