Photo by Brian V. Rowe

Chester Gap Hotels

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Guest rating
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Our top choices for Chester Gap hotels

Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is €92
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1072)
"Very clean, helpful staff"
United States
Kathleen
The price is €93
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn & Suites Winchester
Property amenity
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (554)
"Perfect for one night stay before Skyline Drive trip. "
United States
Timothy
The price is €113
includes taxes & fees
21 Dec - 22 Dec
TownePlace Suites by Marriott Front Royal
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1002)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is €102
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Front Royal
Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (94)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is €290
includes taxes & fees
8 Jan - 9 Jan 2026
Glen Gordon Manor
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is €69
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Winchester South-Stephens City by IHG
Exterior
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
Strasburg
9.0 out of 10, Wonderful, (1000)
"Great stay."
United States
Kenneth
The price is €107
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites Strasburg Shenandoah Valley
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (416)
"Historic inn. "
United States
David
The price is €76
includes taxes & fees
14 Dec - 15 Dec
Wayside Inn
Terrace/patio
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (174)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is €282
includes taxes & fees
21 Dec - 22 Dec
L'Auberge Provencale Inn & Restaurant
Basic Room, 2 Queen Beds, Non Smoking
Hillside

Hillside

Hillside
2.5 star property
Luray
9.0 out of 10, Wonderful, (1000)
"Great location, staff very friendly"
United States
Ines
Hillside
Lobby
Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1001)
"Have stayed here multiple times -always good"
United States
Robert
The price is €78
includes taxes & fees
11 Jan - 12 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (540)
"Great pool and quiet area to stay in"
United States
Matthew
The price is €59
includes taxes & fees
14 Dec - 15 Dec
Twi-Lite Inn
Lift
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.2 out of 10, Very good, (1001)
"Friendly Staff, clean room."
Canada
Frank
The price is €68
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
Family House, Multiple Beds, Balcony, Garden Area | Balcony
Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
United States
Phil
Hopkins Ordinary Bed Breakfast and Ale Works
Property entrance
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
Front Royal
6.4 out of 10, (916)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is €53
includes taxes & fees
23 Dec - 24 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
Property entrance
Blue Ridge Motel

Blue Ridge Motel

Blue Ridge Motel
2.0 star property
Front Royal
7.0 out of 10, Good, (130)
"The housekeeper is so friendly and this is a lovely place to stay if you want that country inn vibe "
United States
Misty
Blue Ridge Motel
Front of property – evening/night
Relax Inn Motel

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very good, (259)
"Clean, and nice rooms, friendly staff"
United States
James
The price is €65
includes taxes & fees
12 Dec - 13 Dec
Relax Inn Motel
Premier Villa, 1 King Bed, Mountain View | Terrace/patio
White Moose Inn

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (147)
"Amazing trip! "
United States
Rebecca
White Moose Inn
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
Front Royal
7.6 out of 10, Good, (1003)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
The price is €56
includes taxes & fees
12 Dec - 13 Dec
Super 8 by Wyndham Front Royal
Free daily continental breakfast
Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
2.5 star property
Stephens City
8.0 out of 10, Very good, (629)
"Good variety at breakfast and courteous staff."
Canada
Madonna
The price is €68
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Stephens City - Winchester South
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 the local area in Chester Gap as you venture to sights like Shenandoah National Park.

See all hotels in Chester Gap
Many butterflies
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Chester Gap Hotel Reviews

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent
"All was well very, nice hotel! Breakfast was great. King size bed was nice, but the mattress was terrible, to soft and lympy, sheets and top cover seemed very worn. The bed wasn't too comfortable. We were in Room 201."
Richard 1-night trip
Posted 4 days ago
Ramada by Wyndham Strasburg/Shenandoah Valley

More cheap stays in Chester Gap

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

10 S Commerce Ave Front Royal VA
The price is €53 per night from 23 Dec to 24 Dec
€53
23 Dec - 24 Dec
includes taxes & fees
6.4/10 (916 reviews)

Frequently asked questions

Where is the best place to stay in Chester Gap?
Comfort Inn & Suites Winchester, located 18.5 mi (29.8 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 Country Inn & Suites by Radisson, Winchester, VA and Ramada by Wyndham Strasburg/Shenandoah Valley. 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?
Secluded River Cabin Getaway (Masten Cabin): This holiday home rental outside of Chester Gap is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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 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.

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