Book Hotels in Chester Gap, VA

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Top Chester Gap hotels

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Fully refundable
$100 nightly
The price is $111 total per night from Aug 9 to Aug 10
$111 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free self-serve breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"Great value, handy location, pet friendly."

Reviewed on Jul 12, 2026

Opens in a new windowComfort Inn & Suites Winchester
Hillside

Hillside

2.5 out of 5
1460 US Highway 211 East Luray VA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $126 total per night from Jul 20 to Jul 21
$126 total
Jul 20 - Jul 21
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and barbecue grills are also on ...
"Clean room, easy parking, friendly staff, scenic vista. Retro vibe but nicely remodeled."

Reviewed on Jul 13, 2026

Opens in a new windowHillside
Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd Front Royal VA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Jul 22 to Jul 23
$145 total
Jul 22 - Jul 23
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference ...
"Was very happy to be allowed to check in early!"

Reviewed on Jul 13, 2026

Opens in a new windowHampton Inn Front Royal
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

3 out of 5
33760 Old Valley Pike Strasburg VA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $131 total per night from Aug 9 to Aug 10
$131 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Very affordable, nice rooms, and conveniently located - greatly enjoyed our stay!"

Reviewed on Jul 12, 2026

Opens in a new windowFairfield Inn & Suites Strasburg Shenandoah Valley
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
Fully refundable
$94 nightly
The price is $104 total per night from Aug 3 to Aug 4
$104 total
Aug 3 - Aug 4
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Just a stopover on way to Pittsburgh. Clean, good enough room. No complaints"

Reviewed on Jul 11, 2026

Opens in a new windowCountry Inn & Suites by Radisson, Winchester, VA
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jul 20 to Jul 21
$90 total
Jul 20 - Jul 21
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests ...
"When we got to our room, we were exhausted and ready to sleep after a ling drive. The bedding was wet. I dont know if the bedding wasnt 100 percent dry when the bed was made or humidity but it was disgusting and not comfortable. We let the front desk know and we were told there is nothing they can ..."

Reviewed on Jul 13, 2026

Opens in a new windowRamada by Wyndham Strasburg/Shenandoah Valley
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

2 out of 5
111 South St Front Royal VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from Jul 15 to Jul 16
$77 total
Jul 15 - Jul 16
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Enjoy the free on-the-go breakfast each morning. A safe deposit box is ...
"The room was clean, but the shower was noisy. The air conditioner was also very loud. The elevator button board was falling apart and there appeared to be graffiti on the elevator door. The staff did not have knowledge about the surrounding area. The free breakfast was meager and the coffee was straight ..."

Reviewed on Jul 12, 2026

Opens in a new windowSuper 8 by Wyndham Front Royal Near Shenandoah National Park
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 out of 5
10 S Commerce Ave Front Royal VA
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $68 total per night from Jul 20 to Jul 21
$68 total
Jul 20 - Jul 21
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy ...
"Room was musty-smelling, we found mold and dead bugs under the bed. We opted not to stay the night. Fortunately Hotels.com was able to get a refund for the stay for us."

Reviewed on Jul 13, 2026

Opens in a new windowBaymont by Wyndham Front Royal Near Shenandoah National Park
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
91 Reliance Road Middletown VA
Fully refundable
$68 nightly
The price is $75 total per night from Jul 20 to Jul 21
$75 total
Jul 20 - Jul 21
Total with taxes and fees
A bar/lounge and a 24-hour front desk are featured at this hotel, along with free self parking. WiFi in public areas is free. Laundry facilities are provided ...
"Believe the reviews. When we arrived, there was a crack-head in front of us with no money trying to negotiate for a room. The check-in person seemed high and didn't bother to stop vaping as she took my ID and checked us in. When I turned on the A/C in the room, a waft of mildew aroma moved across ..."

Reviewed on Jul 9, 2026

Opens in a new windowEcono Lodge Inn & Suites Middletown - Winchester South
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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.

Frequently asked questions

What are the top kid-friendly hotels in Chester Gap?
Family trips are where lifelong memories are made, but traveling with children can be daunting. These kid-friendly Chester Gap hotels come with perks designed to keep visitors of all ages comfortable and happy: You're well catered for at The Nest at Chester Gap. It comes with a king bed, a deck and a knack for making families feel welcome. Otherwise, spend your Chester Gap getaway at Wine_country_mountain_lodge. Take advantage of a swimming pool, a fireplace and more here.
Where can I find cheap hotels in Chester Gap?
At Travelocity you'll find really nice hotels in Chester Gap at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester Gap rather than in Chester Gap. We may find you even better rates, too.
How do I find the best Chester Gap hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester Gap then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester Gap?
The cheapest hotel in Chester Gap is $68. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester Gap?
There are 520 hotels in Chester Gap on Travelocity.
What are the best hotels in Chester Gap?
Chester Gap has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester Gap for you!
When is the best time to visit Chester Gap?
If you want the joy of a fun-filled trip in peak season, visit Chester Gap during January, March and June. If you'd prefer the peace of off-season, book a stay during quieter months, such as September, October and December.
When is the cheapest time to stay in Chester Gap?
Based on historic data is usually the cheapest month to visit Chester Gap. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester Gap?
There are multiple hotels in Chester Gap that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester Gap. We have plenty of kid-friendly hotels in Chester Gap to choose from on Travelocity!
Why book a hotel in Chester Gap through Travelocity?
Because we have the top hotels in Chester Gap! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester Gap on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester Gap hotel reviews by fellow wanderers

Hampton Inn Front Royal

Hampton Inn Front Royal

5 out of 5
Posted 12 hours ago
Travelocity Verified Review
"Was very happy to be allowed to check in early!"
A verified traveler stayed at Hampton Inn Front Royal
Hampton Inn Front Royal

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