Deals on vacations and trips to Chester Gap

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Top Chester Gap hotels deals

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
$81 nightly
The price is $90 total per night
$90 total
Jul 12 - Jul 13
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.
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Free Cancellation
$99 nightly
The price is $108 total per night
$108 total
Jul 27 - Jul 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 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Hillside

Hillside

2.5 out of 5
1460 US Highway 211 East Luray VA
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $126 total per night
$126 total
Jul 5 - Jul 6
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and barbecue grills are also on offer.
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

2 out of 5
91 Reliance Road Middletown VA
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $85 total per night
$85 total
Jul 7 - Jul 8
Total with taxes and fees
A bar/lounge and a 24-hour front desk are featured at this hotel, along with free self parking. WiFi in public areas is free. Laundry facilities are provided for your convenience.
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
$94 nightly
The price is $102 total per night
$102 total
Jul 22 - Jul 23
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.
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
$125 nightly
The price is $138 total per night
$138 total
Jul 27 - Jul 28
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.
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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

Two butterflies on purple flowers.
A field of pink and yellow flowers with a butterfly on one of the pink flowers.