Deals on vacations and trips to Chester Gap

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Top Chester Gap hotels deals

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $105 total per night
$105 total
Jan 25 - Jan 26
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 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $81 total per night
$81 total
Jan 13 - Jan 14
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 will appreciate freebies like daily breakfast and free self parking.
Breakfast included
Pet friendly
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd Winchester VA
Free Cancellation
$83 nightly
The price is $90 total per night
$90 total
Feb 1 - Feb 2
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 appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $108 total per night
$108 total
Jan 11 - Jan 12
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 and free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.
Pool
Hot Tub
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
Get rates
A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

3 out of 5
5 Caroline Drive Front Royal VA
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $132 total per night
$132 total
Jan 11 - Jan 12
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. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
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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

How much are vacation packages to Chester Gap?
With vacation packages available for only , it's not necessary to empty your piggy bank for your trip to Chester Gap. Travelocity is here to help. Bundle your flights, hotels and experiences into a convenient package and land some impressive discounts. The more you book, the more you save.
Where can I get the best vacation package deals for Chester Gap?
It's simple — look no further than Travelocity. With 400 partner airlines and 1,000,000 properties across the globe, it's a breeze to put together a Chester Gap package deal that suits your travel style.
Why should I purchase my Chester Gap vacation bundle with Travelocity?
From amazing destinations to one-of-a-kind experiences, we have everything you need to satisfy your love for travel. Our friendly 24/7 customer support will also make sure you're being taken care of while you're on your vacation. And don't panic if you spot a better price on your reservation, we'll match it. That's our Price Match Guarantee.
Will I save money on my Chester Gap car rental if I bundle it with hotels and flights?
With a Chester Gap vacation package, you can combine your hotel, car and flight bookings and save a tidy sum. When you're ready to discover the best of this impressive location, why not start with White House? This top sight is 60 mi from Chester Gap. With your own wheels, you'll be there belong long.
Which airport is best for Chester Gap?
It's very likely you'll touch down at Ronald Reagan Washington National Airport (DCA), situated 60 mi east of inner Chester Gap. Washington Dulles Intl. Airport (IAD) (40 mi away from central Chester Gap) and Charlottesville-Albemarle Airport (CHO) (50 mi away from central Chester Gap) are other options.
Where should I stay when visiting Chester Gap?
Many travelers opt to check in to the Modern Mountain Retreat w/ Deck + Hot Tub!. It's sure to be a good base for your Chester Gap escape.

Photos of local treasures

Browse Chester Gap vacation photos for more inspiration

Photo by Brian V. Rowe
Photo by Brian V. Rowe
Photo by Brian V. Rowe
Photo by Brian V. Rowe
Photo by Brian V. Rowe
Photo by Brian V. Rowe