Book Hotels in Chester Gap, VA

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Top Chester Gap hotels

Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!

Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!

Rileyville VA
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly.

Reviewed on Feb 18, 2026

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Opens in a new windowFalling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Fully refundable
$103 nightly
The price is $112 total per night from Apr 27 to Apr 28
$112 total
Apr 27 - Apr 28
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 ...
Staff was very friendly, clean room and great breakfast!

Reviewed on Mar 30, 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
$102 nightly
The price is $113 total per night from Apr 26 to Apr 27
$113 total
Apr 26 - Apr 27
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 ...
While everything was great, I was most impressed by the customer service from all of the staff.

Reviewed on Mar 30, 2026

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
$105 nightly
The price is $116 total per night from Apr 26 to Apr 27
$116 total
Apr 26 - Apr 27
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, clean premises

Reviewed on Mar 31, 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
$91 nightly
The price is $99 total per night from Apr 21 to Apr 22
$99 total
Apr 21 - Apr 22
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 room was clean. The breakfast was well stocked and the attendants kept in very clean.

Reviewed on Mar 31, 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
$79 nightly
The price is $88 total per night from Apr 15 to Apr 16
$88 total
Apr 15 - Apr 16
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 ...
Check-in was easy, even though it was at 11 pm. The room smelled horribly musty. The bed, pillows, covers could all use updating. The telephone wasn't even connected to the wall so there was no way to call the front desk or any outside line. The breakfast was surprisingly pretty good. For the price, ...

Reviewed on Mar 30, 2026

Opens in a new windowRamada by Wyndham Strasburg/Shenandoah Valley
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 out of 5
165 Town Run Ln Stephens City VA
Fully refundable
$97 nightly
The price is $106 total per night from Apr 5 to Apr 6
$106 total
Apr 5 - Apr 6
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. ...
The hotel is fine, nothing fancy of course as that's not expected. However, our key cards did not consistently work so I had to go down to the front desk twice. Also, the ice machine is on the 1st floor, and I prefer it be on the same floor as our room.

Reviewed on Mar 23, 2026

Opens in a new windowHoliday Inn Express Winchester South-Stephens City by IHG
Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South

2.5 out of 5
167 Town Run Ln Stephens City VA
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $90 total per night from Apr 13 to Apr 14
$90 total
Apr 13 - Apr 14
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
Great location safe area clean rooms good price

Reviewed on Mar 22, 2026

Opens in a new windowQuality Inn Stephens City - Winchester South
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
$65 nightly
The price is $72 total per night from Apr 5 to Apr 6
$72 total
Apr 5 - Apr 6
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 ...
Breakfast options were minimal.

Reviewed on Mar 26, 2026

Opens in a new windowSuper 8 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 $72. 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 511 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

Hillside

Hillside

5 out of 5
Posted 9 hours ago
Travelocity Verified Review
"The room was so lovely and comfortable and the staffperson was very nice and helpful. "
A verified traveler stayed at Hillside
Hillside

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