Photo by Brian V. Rowe

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Top hotels and accommodation in Chester Gap

Comfort Inn & Suites Winchester

2.5 star property
9.4 out of 10, Exceptional, (1003)
"Perfect stay for our family while on the road"
The price is AU$162
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Winchester

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1003)
"Great place to stay!"
The price is AU$159
includes taxes & fees
13 Aug - 14 Aug
Country Inn & Suites by Radisson, Winchester, VA

Hampton Inn Front Royal

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Great stay"
The price is AU$187
includes taxes & fees
24 Aug - 25 Aug
Hampton Inn Front Royal

TownePlace Suites by Marriott Front Royal

3.0 star property
9.6 out of 10, Exceptional, (524)
"Breakfast was awesome, hit coffee available all day, clean rooms and great staff!"
The price is AU$235
includes taxes & fees
17 Aug - 18 Aug
TownePlace Suites by Marriott Front Royal

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Everything was fine; nothing outstanding but nothing bad either. Good place for an overnight stay while traveling "
The price is AU$193
includes taxes & fees
24 Aug - 25 Aug
Fairfield Inn & Suites Strasburg Shenandoah Valley

Hillside

2.5 star property
9.0 out of 10, Wonderful, (959)
"Charming stay at Hillside! Clean rooms, friendly staff, and close to beautiful mountain views. Perfect spot for visiting Shenandoah and Luray Caverns. Great value and peaceful vibes!"
Hillside

White Moose Inn

4.0 star property
9.8 out of 10, Exceptional, (142)
"Wonderful option if visiting inn at little Washington or other sites nearby. Just a bock from inn with very helpful staff,happy hour, full breakfast and clean comfortable accommodations "
White Moose Inn

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1001)
"Convenient to Skyline Drive in Shenandoah National Park."
The price is AU$118
includes taxes & fees
12 Aug - 13 Aug
Super 8 by Wyndham Front Royal

Twi-Lite Inn

2.0 star property
8.2 out of 10, Very good, (517)
"Great pool and quiet area to stay in"
The price is AU$133
includes taxes & fees
12 Aug - 13 Aug
Twi-Lite Inn

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Fantastic stay, thanks!"
The price is AU$176
includes taxes & fees
24 Aug - 25 Aug
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Relax Inn Motel

2.0 star property
8.2 out of 10, Very good, (238)
"Clean, quiet and convenient. Check in process was quick and easy, with the very friendly and helpful staff. I would absolutely stay here again."
The price is AU$106
includes taxes & fees
12 Aug - 13 Aug
Relax Inn Motel

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very good, (598)
"Great stay!"
The price is AU$117
includes taxes & fees
1 Sept - 2 Sept
Quality Inn Stephens City - Winchester South

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very good, (762)
"Always great!"
The price is AU$133
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn Express Winchester South-Stephens City by IHG

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.2 out of 10, Very good, (1012)
"Service was great "
The price is AU$115
includes taxes & fees
1 Sept - 2 Sept
Ramada by Wyndham Strasburg/Shenandoah Valley

L'Auberge Provencale Inn & Restaurant

4.0 star property
9.6 out of 10, Exceptional, (167)
"Beautiful historic property well maintained and on the way to Skyline Drive. Breakfast was divine!"
The price is AU$400
includes taxes & fees
25 Aug - 26 Aug
L'Auberge Provencale Inn & Restaurant

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (89)
"The location is good."
The price is AU$417
includes taxes & fees
19 Aug - 20 Aug
Glen Gordon Manor

Hopkins Ordinary Bed Breakfast and Ale Works

3.0 star property
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
Hopkins Ordinary Bed Breakfast and Ale Works

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (402)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere. "
The price is AU$166
includes taxes & fees
24 Aug - 25 Aug
Wayside Inn

The Foster Harris House

2.0 star property
10.0 out of 10, Exceptional, (1)
"Lovely inn in a great location three course breakfast with one of the best scones I have eaten "
The price is AU$825
includes taxes & fees
13 Aug - 14 Aug
The Foster Harris House

Motel 6 Front Royal, VA

2.0 star property
6.8 out of 10, (481)
"This is a great location! "
The price is AU$105
includes taxes & fees
24 Aug - 25 Aug
Motel 6 Front Royal, VA
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.
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Learn more about Chester Gap

Check out popular sights like Shenandoah National Park as you discover the local area in Chester Gap.

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

Top Chester Gap Hotel Reviews

Frequently asked questions

Where is the best place to stay in Chester Gap?

Ramada by Wyndham Strasburg/Shenandoah Valley, located 15.2 mi (24.5 km) from the heart of Chester Gap, is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Comfort Inn & Suites Winchester and Country Inn & Suites by Radisson, Winchester, VA. See all available top hotels, or vacation rentals in Chester Gap.

What are some of the best holiday rentals that Chester Gap has to offer?

Modern Mountain Retreat w/ Deck + Hot Tub!: This highly rated holiday home rental in Chester Gap offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. See all vacation rentals in Chester Gap.

If I need to cancel my hotel reservation in Chester Gap, will I receive a refund?

Yes! Most room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester Gap.

What are some hotels with pools in Chester Gap?

The Hillside Motel: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Winchester, VA and Hampton Inn Front Royal are two additional hotels that feature an on-site pool. View all hotels with pools in Chester Gap.

What is the best spa hotel in Chester Gap?
What is staying in Chester Gap like?

Visitors will definitely enjoy all that Chester Gap has to offer. A top sight in the city is Shenandoah National Park. In Chester Gap, there are 4 hotels and other accommodation options to choose from. Find out more about Chester Gap.

What should I do while I'm visiting Chester Gap?

A favourite place to visit is Shenandoah National Park. You'll also find Dickey Ridge Visitor Center and Linden Vineyards in the area. Take a look at what more there is to see and do in Expedia's Chester Gap guide.

What's the seasonal weather in Chester Gap?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Chester Gap is 1184 mm.