Book Hotels in Chester Gap, VA

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Top Chester Gap hotels

Lookout Cabin in the mountains, Amazing Views!

Lookout Cabin in the mountains, Amazing Views!

Page County VA
$348 nightly
The price is $383 total per night from Jan 12 to Jan 13
$383 total
Jan 12 - Jan 13
Total with taxes and fees
A hot tub is featured at this cabin, along with barbecue grills.
What a Sscenic and peaceful stay at this cabin! The views were just incredible and so were the sunsets. The cabin was very clean and cozy. Our dog loved the walk to the waterfall down the road. Brian, the property manager, was very responsive and helpful. Will definitely book again!

Reviewed on Nov 25, 2025

Opens in a new windowLookout Cabin in the mountains, Amazing Views!
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
It was very nice, peaceful and relaxing! Very cozy. Had everything we needed. Great view too!

Reviewed on Dec 8, 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
$98 nightly
The price is $107 total per night from Feb 8 to Feb 9
$107 total
Feb 8 - Feb 9
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 staff

Reviewed on Jan 6, 2026

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
$112 nightly
The price is $123 total per night from Jan 13 to Jan 14
$123 total
Jan 13 - Jan 14
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. ...
Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants.

Reviewed on Dec 26, 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
$98 nightly
The price is $109 total per night from Jan 15 to Jan 16
$109 total
Jan 15 - Jan 16
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 ...
Front desk staff very friendly

Reviewed on Dec 29, 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
$98 nightly
The price is $108 total per night from Jan 15 to Jan 16
$108 total
Jan 15 - Jan 16
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 ...
did not eat breakfast

Reviewed on Jan 3, 2026

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
$84 nightly
The price is $92 total per night from Feb 8 to Feb 9
$92 total
Feb 8 - Feb 9
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 ...
It was all totally smooth

Reviewed on Jan 7, 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
$73 nightly
The price is $81 total per night from Jan 20 to Jan 21
$81 total
Jan 20 - Jan 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 ...
Breakfast fresh, good coffee, enough healthy variety

Reviewed on Jan 6, 2026

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
$62 nightly
The price is $69 total per night from Jan 10 to Jan 11
$69 total
Jan 10 - Jan 11
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 ...
Good condition

Reviewed on Dec 26, 2025

Opens in a new windowSuper 8 by Wyndham Front Royal
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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 $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 514 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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"It was all totally smooth "
A verified traveler stayed at Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA

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