Photo by Brian V. Rowe

Find hotels in Chester Gap, VA from NT$1,917

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Dec 11 - Dec 12
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Dec 12 - Dec 13
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Dec 12 - Dec 14
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Dec 19 - Dec 21

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Our top choices for Chester Gap hotels

Exterior
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 NT$2,307
NT$2,511 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Winchester South-Stephens City by IHG
Lobby
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 NT$2,227
NT$2,479 total
includes taxes & fees
Jan 1 - 2026/1/2
Ramada by Wyndham Strasburg/Shenandoah Valley
Basic Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free WiFi, bed sheets
Hillside

Hillside

Hillside
2.5 star property
Luray
9.0 out of 10, Wonderful, (1000)
"Great location, staff very friendly"
United States
Ines
Hillside
Breakfast area
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
The price is NT$1,936
NT$2,136 total
includes taxes & fees
Dec 21 - Dec 22
Econo Lodge Inn & Suites Middletown - Winchester South
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 NT$2,279
NT$2,480 total
includes taxes & fees
Jan 11 - 2026/1/12
Quality Inn Stephens City - Winchester South
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 NT$3,043
NT$3,450 total
includes taxes & fees
Dec 17 - Dec 18
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1001)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is NT$3,343
NT$3,720 total
includes taxes & fees
Dec 17 - Dec 18
Hampton Inn Front Royal
Garden
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 NT$9,323
NT$10,284 total
includes taxes & fees
Dec 17 - Dec 18
L'Auberge Provencale Inn & Restaurant
Lobby lounge
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 NT$3,524
NT$3,922 total
includes taxes & fees
Dec 15 - Dec 16
Fairfield Inn & Suites Strasburg Shenandoah Valley
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 NT$1,840
NT$2,048 total
includes taxes & fees
Dec 13 - Dec 14
Super 8 by Wyndham Front Royal
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 NT$3,136
NT$3,411 total
includes taxes & fees
Jan 11 - 2026/1/12
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 NT$3,679
NT$4,121 total
includes taxes & fees
Dec 21 - Dec 22
TownePlace Suites by Marriott Front Royal
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 NT$2,630
NT$2,862 total
includes taxes & fees
Jan 11 - 2026/1/12
Country Inn & Suites by Radisson, Winchester, VA
Seasonal outdoor pool
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 NT$1,933
NT$2,152 total
includes taxes & fees
Dec 14 - Dec 15
Twi-Lite Inn
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 NT$9,640
NT$10,536 total
includes taxes & fees
Jan 8 - 2026/1/9
Glen Gordon Manor
Lobby
Motel 6 Front Royal, VA

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
Front Royal
6.8 out of 10, (500)
"perfect for an affordable stay near Shenandoah. Clean, no one bothered me. Walkable to a Chinese restaurant. "
United States
Ariella
The price is NT$1,871
NT$2,082 total
includes taxes & fees
Dec 24 - Dec 25
Motel 6 Front Royal, VA
Porch
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 NT$2,120
NT$2,360 total
includes taxes & fees
Dec 14 - Dec 15
Relax Inn Motel
Garden
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
Porch
Gay Street Inn

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is NT$11,194
NT$12,067 total
includes taxes & fees
Jan 1 - 2026/1/2
Gay Street Inn
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.

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 NT$1,723 per night from Dec 23 to Dec 24
NT$1,723
NT$1,917 total
Dec 23 - Dec 24
includes taxes & fees
6.4/10 (916 reviews)

Hotels in Chester Gap with star-rating

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 traveler data. Other good options for your stay in 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.
If I need to cancel my hotel reservation in Chester Gap, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester Gap.
Where can I learn more about changing or cancelling my trip to Chester Gap?
To access more information about updating your trip to Chester Gap or cancelling it, go to https://www.expedia.com/service/.
What is staying in Chester Gap like?
Visitors are sure to 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 accommodations to choose from. Find out more about Chester Gap.
What are the top places to visit in Chester Gap?
A favorite place to visit is Shenandoah National Park. You'll also find Dickey Ridge Visitor Center and Linden Vineyards in the area. Check out what more to see and do in Expedia's Chester Gap guide.
What's the seasonal weather like in Chester Gap?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Chester Gap is 47 inches.

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