Book Hotels in Chester Gap, VA

Start date: Check-in selected.
To Date
End date: Check-out

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
Amenities
Amenities
Accessibility
Accessibility

Top Chester Gap hotels

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
It's a great place for 2 people, the main bathroom is on the first floor, the best bedroom is upstairs.

Reviewed on Oct 14, 2025

Opens in a new windowFalling Leaf Cabin - Rustic Charm With Modern Decor!
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
$101 nightly
The price is $110 total per night from Nov 21 to Nov 22
$110 total
Nov 21 - Nov 22
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 ...
Lovely one night stay while traveling through the area. The bed was comfortable, room was clean, and breakfast was tasty. I would certainly stay here again.

Reviewed on Nov 3, 2025

Opens in a new windowComfort Inn & Suites Winchester
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

3 out of 5
5 Caroline Drive, Front Royal, VA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $142 total per night from Nov 9 to Nov 10
$142 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
Everythign was great. staff was friendly and room was clean. Complimentary breakfast was good.

Reviewed on Oct 23, 2025

Opens in a new windowTownePlace Suites by Marriott Front Royal
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
$110 nightly
The price is $123 total per night from Nov 23 to Nov 24
$123 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
The staff was amazing! As we zipped in and out we were always welcomed or wished a good day. Big smiles and just super nice! Loved the coffee/tea area. Talk about coming home. My one comment would be that the trash cans were never emptied in our room or bathroom. And because the cans are so small ...

Reviewed on Oct 28, 2025

Opens in a new windowHampton Inn Front Royal
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
$109 nightly
The price is $120 total per night from Nov 16 to Nov 17
$120 total
Nov 16 - Nov 17
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 ...
Friendly staff, nice clean room, hotel restaurant was delicious.

Reviewed on Nov 1, 2025

Opens in a new windowDoubleTree by Hilton Front Royal Blue Ridge Shadows
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
$91 nightly
The price is $99 total per night from Nov 26 to Nov 27
$99 total
Nov 26 - Nov 27
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 ...
The hotel itself was clean and well maintained. The local was particularly good as there was easy access to major highways and multiple area dining options. The only problem I had was the included hot breakfast. There was no coffee available and they were running out of food early into the breakfast ...

Reviewed on Nov 3, 2025

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, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Nov 23 to Nov 24
$80 total
Nov 23 - Nov 24
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 ...
Great!

Reviewed on Nov 2, 2025

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

Super 8 by Wyndham Front Royal

2 out of 5
111 South St, Front Royal, VA
Fully refundableReserve now, pay when you stay
$53 nightly
The price is $59 total per night from Dec 4 to Dec 5
$59 total
Dec 4 - Dec 5
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like on-the-go breakfast and WiFi in ...
very clean room

Reviewed on Nov 2, 2025

Opens in a new windowSuper 8 by Wyndham Front Royal
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
$58 nightly
The price is $64 total per night from Nov 23 to Nov 24
$64 total
Nov 23 - Nov 24
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 ...
It was very pleasant to check in. The attendant was very helpful. The room is clean.

Reviewed on Oct 30, 2025

Opens in a new windowBaymont 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 $59. 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 509 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

Explore More Ways to Travel with Travelocity