Book Hotels in Chester Gap, VA

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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

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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
The price is $110 total per night from Nov 21 to Nov 22
$110 total
per night
Nov 21 - Nov 22
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 ...
Staff was very friendly, room clean and neat.

Reviewed on Nov 14, 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
The price is $142 total per night from Nov 23 to Nov 24
$142 total
per night
Nov 23 - Nov 24
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. ...
Our family enjoyed our stay at Towneplace Suites Front Royal. We always choose Towneplace suites when we travel because of the breakfast and spacious rooms. This hotel, however, was unique because of the warm and friendly staff. We checked in late and were greeted warmly. Throughout our stay, Britany ...

Reviewed on Nov 10, 2025

Opens in a new windowTownePlace Suites by Marriott 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
The price is $134 total per night from Nov 23 to Nov 24
$134 total
per night
Nov 23 - Nov 24
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 ...
Staff was friendly and kind. It was nice to get a cookie and bottle of water when you check in. Bed were overly firm and uncomfortable, while pillows were overly soft and not supportive. Location was great for Shenandoah National Park and lot's of good places to eat nearby.

Reviewed on Nov 9, 2025

Opens in a new windowDoubleTree by Hilton Front Royal Blue Ridge Shadows
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
The price is $106 total per night from Nov 30 to Dec 1
$106 total
per night
Nov 30 - Dec 1
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 ...
Yes

Reviewed on Nov 10, 2025

Opens in a new windowHampton Inn Front Royal
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
The price is $105 total per night from Nov 30 to Dec 1
$105 total
per night
Nov 30 - Dec 1
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 ...
Ws a clean and comfy place

Reviewed on Nov 14, 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
The price is $82 total per night from Nov 24 to Nov 25
$82 total
per night
Nov 24 - Nov 25
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 ...
Yes

Reviewed on Nov 15, 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
The price is $73 total per night from Dec 1 to Dec 2
$73 total
per night
Dec 1 - Dec 2
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 ...
Courteous staff at foyer and breakfast. The "things that go bump in the night" continued until about midnight, then the halls quieted down quite a bit. The king-sized bed was clean but a soft mattress. Wifi and T.V. service was good.wa

Reviewed on Nov 9, 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
The price is $61 total per night from Dec 1 to Dec 2
$61 total
per night
Dec 1 - Dec 2
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 ...
The room was clean and very large. Breakfast had hot options like eggs etc. Pretty much standard for IHG. Breakfast stuff was on top of everything all the time and really took care of the area nicely. Would go to this hotel again very nice

Reviewed on Nov 7, 2025

Opens in a new windowBaymont by Wyndham Front Royal Near Shenandoah National Park
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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 $61. 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 508 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

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Yes"
A verified traveler stayed at Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah Valley

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