Photo by Brian V. Rowe

Find hotels in Chester Gap, VA from NT$1,918

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

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, (1001)
Scenic Front Royal hotel with an 18-hole golf course just 15 minutes from Shenandoah National Park. Unwind in the indoor pool after a day outdoors, enjoy American cuisine at Houlihan's Restaurant, or relax at the bar. Free WiFi and parking add convenience.
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is NT$3,044
NT$3,358 total
includes taxes & fees
Dec 21 - Dec 22
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, (1073)
Near Appleland Sports Center and Kernstown Battlefield, this hotel offers a 24-hour fitness center and complimentary WiFi. Guests praise the comfortable beds, helpful staff, and daily breakfast served from 6:00 AM on weekdays.
"Very clean, helpful staff"
United States
Kathleen
The price is NT$3,120
NT$3,394 total
includes taxes & fees
Jan 12 - 2026/1/13
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)
Conveniently located 15 minutes from Shenandoah National Park, this hotel offers free breakfast, WiFi, and parking. Enjoy the seasonal outdoor pool or maintain fitness in the 24-hour gym. Clean rooms and helpful staff ensure a comfortable stay near Blue Ridge Shadows Golf Club.
"Perfect for one night stay before Skyline Drive trip. "
United States
Timothy
The price is NT$3,681
NT$4,123 total
includes taxes & fees
Dec 21 - Dec 22
TownePlace Suites by Marriott Front Royal
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, (1002)
Just 15 minutes from Shenandoah National Park, this hotel offers 24-hour fitness facilities and an indoor pool. Guests love the helpful staff, free breakfast, WiFi, and parking, with Shenandoah River nearby.
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is NT$3,344
NT$3,722 total
includes taxes & fees
Dec 21 - Dec 22
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)
Indulge in countryside elegance at this B&B just minutes from Shenandoah National Park. Enjoy complimentary breakfast before exploring nearby wineries, then return for massages and seasonal swimming. The 24-hour fitness center and bar complete your getaway.
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is NT$9,660
NT$10,559 total
includes taxes & fees
Jan 8 - 2026/1/9
Glen Gordon Manor
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$2,309
NT$2,512 total
includes taxes & fees
Dec 20 - Dec 21
Holiday Inn Express Winchester South-Stephens City by IHG
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$3,525
NT$3,923 total
includes taxes & fees
Dec 16 - Dec 17
Fairfield Inn & Suites Strasburg Shenandoah Valley
Dining
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 NT$2,246
NT$2,789 total
includes taxes & fees
Dec 15 - Dec 16
Wayside 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)
Savor local cuisine at La Table Provencale after swimming in the seasonal outdoor pool. This business-friendly inn provides spa services, complimentary breakfast, and free parking. Enjoy easy access to White Post Village Park while receiving attentive service from the staff.
"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$9,348
NT$10,310 total
includes taxes & fees
Dec 15 - Dec 16
L'Auberge Provencale Inn & Restaurant
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)
Nestled close to Shenandoah National Park, this motel offers a refreshing seasonal outdoor pool after a day of exploration. Enjoy complimentary parking and WiFi while staying just minutes from popular Luray Caverns and Yogi Bear's Jellystone Park.
"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, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is NT$2,636
NT$2,868 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$1,934
NT$2,153 total
includes taxes & fees
Dec 16 - Dec 17
Twi-Lite Inn
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, (1003)
Savor Civil War history at this Strasburg retreat with fitness center and restaurant. Located near Hupp's Hill Civil War Park and Strasburg Museum, this hotel offers complimentary breakfast, WiFi, and parking that guests consistently praise.
"Friendly Staff, clean room."
Canada
Frank
The price is NT$2,232
NT$2,484 total
includes taxes & fees
Jan 1 - 2026/1/2
Ramada by Wyndham Strasburg/Shenandoah Valley
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)
Enjoy hiking trails near this charming B&B that crafts its own ales. Start your day with complimentary full breakfast before exploring nearby Copper Fox Distillery and River District Arts. The garden and terrace offer peaceful spots to unwind after outdoor adventures.
"Great place. Good food, great beer."
United States
Phil
Hopkins Ordinary Bed Breakfast and Ale Works
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, (916)
Located 5 minutes from Shenandoah National Park, this tranquil retreat offers a seasonal outdoor pool and onsite dining with bar. Guests praise the helpful staff and quiet rooms. Explore nearby attractions or relax on the terrace after a day of adventure.
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is NT$1,724
NT$1,918 total
includes taxes & fees
Dec 23 - Dec 24
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)
Explore the beauty of Shenandoah from this convenient motel near Bing Crosby Stadium and Shenandoah River. Free WiFi and parking make your adventure seamless, with daily housekeeping ensuring comfort after days of outdoor exploration.
"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
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 rooms await at this convenient Front Royal motel, just 10 minutes from Shenandoah National Park. Free WiFi and parking make exploring nearby Bing Crosby Stadium and Shenandoah River hassle-free, while the 24-hour front desk ensures assistance whenever needed.
"Clean, and nice rooms, friendly staff"
United States
James
The price is NT$2,121
NT$2,361 total
includes taxes & fees
Dec 25 - Dec 26
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)
Just 15 minutes from Shenandoah National Park, this inviting inn provides free breakfast, WiFi, and bike rentals for mountain exploration. Discover nearby hiking trails, relax in the garden, or visit charming local attractions like R.H. Ballard Gallery.
"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, (1005)
Minutes from Shenandoah National Park, this Front Royal hotel offers complimentary WiFi and daily on-the-go breakfast. Guests appreciate the helpful staff and clean rooms. Blue Ridge Arts Council is nearby.
"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$1,841
NT$2,049 total
includes taxes & fees
Dec 17 - Dec 18
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, (630)
Set in charming Stephens City, this hotel offers a serene atmosphere and fitness center. Guests praise the helpful staff, while free breakfast, WiFi, and parking enhance the value. Valerie Hill Winery and local attractions await just minutes away.
"Good variety at breakfast and courteous staff."
Canada
Madonna
The price is NT$2,285
NT$2,486 total
includes taxes & fees
Jan 11 - 2026/1/12
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.
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

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 5 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$1,724 per night from Dec 23 to Dec 24
NT$1,724
NT$1,918 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.

Explore a world of travel with Expedia