Chester Gap

Travel Guide

Chester Gap
Chester Gap
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 $117 per night from May 26 to May 27
CA $117
CA $130 total
May 26 - May 27
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 ...
8.4/10 Very Good! (1,000 reviews)
The hotel and room were okay, and the breakfast was good. However, I was disappointed to find a large stain on my sheets that I didn’t notice until the morning. As far as the checkout experience. I waited about 15 minutes for someone to come to the front desk, but no one showed up. While I was standing ...

Reviewed on Apr 27, 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 $142 per night from May 24 to May 25
CA $142
CA $155 total
May 24 - May 25
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 ...
9.4/10 Exceptional! (1,108 reviews)
Staff and property was great

Reviewed on Apr 29, 2026

Comfort Inn & Suites Winchester
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
The price is CA $150 per night from May 17 to May 18
CA $150
CA $167 total
May 17 - May 18
includes taxes & fees
Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,006 reviews)
Wonderful hotel and stay. Would recommend to anyone.

Reviewed on Apr 27, 2026

Hampton Inn Front Royal
See all 516 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.
The Nest at Chester Gap

The Nest at Chester Gap

Chester Gap VA
Stay at this vacation home in Chester Gap. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chester Gap Cellars and Rappahannock Cellars ...
10/10 Exceptional! (108 reviews)
Great place to get away. Wonderful host and amazing views!

Reviewed on Mar 16, 2026

The Nest at Chester Gap
Whiskey Hill Cabin a mountain escape in Virginia wine country

Whiskey Hill Cabin a mountain escape in Virginia wine country

Linden VA
Stay at this cabin in Front Royal. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Deer Lake and George Richard Thompson State Wildlife ...
10/10 Exceptional! (109 reviews)
We stayed at Whiskey Hill for a combo Mom’s getaway and a friends birthday. It was exactly what we needed. Quiet, lots of beautiful scenery and just relaxing! The beds were great. The kitchen had everything we needed. The instructions of everything were spot on. All in all, we would definitely stay ...

Reviewed on Apr 13, 2026

Whiskey Hill Cabin a mountain escape in Virginia wine country
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Rileyville VA
Stay at this vacation home in Rileyville. Enjoy free WiFi, a garden, and patios. Popular attractions Chalybeate Spring and Elkwallow Picnic Area are located ...
9.6/10 Exceptional! (212 reviews)
Wonderful place to step out of reality for a few days. Our host was great!

Reviewed on Apr 13, 2026

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
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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