Photo by Brian V. Rowe

Find hotels in Chester Gap, VA from ฿1,914

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is ฿3,037
฿3,350 total
includes taxes & fees
29 Dec - 30 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, (1090)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is ฿3,019
฿3,284 total
includes taxes & fees
5 Jan - 6 Jan 2026
Comfort Inn & Suites Winchester
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, (1000)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is ฿3,548
฿3,948 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn Front Royal
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, (1002)
"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 ฿1,930
฿2,148 total
includes taxes & fees
25 Dec - 26 Dec
Super 8 by Wyndham Front Royal
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, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is ฿2,303
฿2,506 total
includes taxes & fees
31 Dec - 1 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
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, (556)
"Very good overall experience."
United States
Douglas
The price is ฿3,673
฿4,113 total
includes taxes & fees
28 Dec - 29 Dec
TownePlace Suites by Marriott Front Royal
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, (1002)
"Great stay."
United States
Kenneth
The price is ฿3,517
฿3,914 total
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites Strasburg Shenandoah Valley
Lobby
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very good, (1000)
"Breakfast was delicious "
United States
Robert
The price is ฿2,222
฿2,473 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
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 ฿2,575
฿2,801 total
includes taxes & fees
18 Jan - 19 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (95)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is ฿8,372
฿9,151 total
includes taxes & fees
20 Jan - 21 Jan 2026
Glen Gordon Manor
Dining
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is ฿2,241
฿2,783 total
includes taxes & fees
28 Dec - 29 Dec
Wayside Inn
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 ฿1,930
฿2,148 total
includes taxes & fees
25 Dec - 26 Dec
Twi-Lite Inn
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 ฿7,127
฿7,862 total
includes taxes & fees
4 Jan - 5 Jan 2026
L'Auberge Provencale Inn & Restaurant
Winery
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, (920)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is ฿1,720
฿1,914 total
includes taxes & fees
30 Dec - 31 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
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 ฿2,116
฿2,355 total
includes taxes & fees
25 Dec - 26 Dec
Relax Inn Motel
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
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
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, (632)
"Good variety at breakfast and courteous staff."
Canada
Madonna
The price is ฿2,296
฿2,498 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Stephens City - Winchester South
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, (501)
"perfect for an affordable stay near Shenandoah. Clean, no one bothered me. Walkable to a Chinese restaurant. "
United States
Ariella
The price is ฿1,774
฿1,975 total
includes taxes & fees
1 Jan - 2 Jan 2026
Motel 6 Front Royal, VA
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"Nice, clean, quiet rooms. Staff were polite and professional. I would stay here again. "
JAMES 2-night trip
Posted 1 month ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

10/10 Excellent
"Room was fine."
William 3-night trip
Posted 2 months ago
Econo Lodge Inn & Suites

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 ฿1,720 per night from 30 Dec to 31 Dec
฿1,720
฿1,914 total
30 Dec - 31 Dec
includes taxes & fees
6.4/10 (918 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 Hampton Inn Front Royal and DoubleTree by Hilton Front Royal Blue Ridge Shadows. 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! 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 to Chester Gap will definitely find plenty to explore and enjoy. 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 Linden Vineyards and Front Royal Entrance Shenandoah National Park 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.