Book Hotels in Chester Gap, VA

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

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
$93 nightly
The price is $103 total per night from Oct 4 to Oct 5
$103 total
Oct 4 - Oct 5
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 place. Quiet and comfortable. Easy access to Interstate 81. There are several good restaurants withing walking distance. Breakfast was fine. We always stay here when we are traveling from NC to NY."

Reviewed on Sep 8, 2026

Opens in a new windowComfort Inn & Suites Winchester
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
$122 nightly
The price is $136 total per night from Sep 27 to Sep 28
$136 total
Sep 27 - Sep 28
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 ...
"Staff and hotel very clean and affordable, breakfast had different selection every morning"

Reviewed on Sep 8, 2026

Opens in a new windowHampton Inn Front Royal
Hillside

Hillside

2.5 out of 5
1460 US Highway 211 East Luray VA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $130 total per night from Sep 9 to Sep 10
$130 total
Sep 9 - Sep 10
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 ...
"Room was clean but not efficient for two adults with luggage. Bathroom needs a simple vanity or shelf on which to place personal hygiene items. Bedroom needs more space on which to place open luggage. Too much money for the value of the stay."

Reviewed on Sep 3, 2026

Opens in a new windowHillside
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
$123 nightly
The price is $136 total per night from Sep 15 to Sep 16
$136 total
Sep 15 - Sep 16
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 ...
"Clean. Friendly and helpful staff. Good location. Safe."

Reviewed on Sep 6, 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
$101 nightly
The price is $113 total per night from Oct 4 to Oct 5
$113 total
Oct 4 - Oct 5
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 ...
"Everything was great! Only odd thing was during one of the days there was an awful smell. The staff said it was the grease trap but it smelt like sewer or an overflowed toilet. Ended up leaving for a few hours and thankfully it was gone. Other then that it was a great stay and the kids loved being ..."

Reviewed on Sep 8, 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
$75 nightly
The price is $83 total per night from Sep 27 to Sep 28
$83 total
Sep 27 - Sep 28
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 ...
"Stay was fine. Pillow covers need better cleaning and bed sheets. Replace the ones with stains on them."

Reviewed on Sep 7, 2026

Opens in a new windowRamada by Wyndham Strasburg/Shenandoah Valley
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
$62 nightly
The price is $69 total per night from Oct 4 to Oct 5
$69 total
Oct 4 - Oct 5
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 ...
"Everyone was very friendly. The small"

Reviewed on Sep 8, 2026

Opens in a new windowBaymont by Wyndham Front Royal Near Shenandoah National Park
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4 out of 5
111 Hospitality Drive Front Royal VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $135 total per night from Sep 20 to Sep 21
$135 total
Sep 20 - Sep 21
Total with taxes and fees
A golf course, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center ...
Opens in a new windowDoubleTree by Hilton Front Royal Blue Ridge Shadows
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
$66 nightly
The price is $73 total per night from Oct 4 to Oct 5
$73 total
Oct 4 - Oct 5
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 ...
Opens in a new windowSuper 8 by Wyndham Front Royal Near Shenandoah National Park
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.

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 $69. 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 534 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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Great place. Quiet and comfortable. Easy access to Interstate 81. There are several good restaurants withing walking distance. Breakfast was fine. We always stay here when we are traveling from NC to NY."
A verified traveler stayed at Comfort Inn & Suites Winchester
Comfort Inn & Suites Winchester

Explore More Ways to Travel with Travelocity