Photo by Brian V. Rowe

Chester Gap hotels from RM251

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
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester Gap hotels

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)
Savour 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 RM1,017
RM1,122 total
includes taxes & fees
21 Dec - 22 Dec
L'Auberge Provencale Inn & Restaurant
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)
Savour Civil War history at this Strasburg retreat with fitness centre 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.
"Breakfast was delicious "
United States
Robert
The price is RM295
RM329 total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
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 RM413
RM460 total
includes taxes & fees
31 Dec - 1 Jan 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
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
Iron/ironing board, free WiFi, bed sheets
Hillside

Hillside

Hillside
2.5 star property
Luray
9.0 out of 10, Wonderful, (1001)
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
Interior detail
Gay Street Inn

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
Surrounded by lush gardens, this charming B&B offers free WiFi and parking near Little Washington Theatre. The peaceful terrace provides a perfect retreat after exploring nearby Shenandoah National Park.
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is RM1,467
RM1,581 total
includes taxes & fees
1 Jan - 2 Jan 2026
Gay Street Inn
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 RM294
RM365 total
includes taxes & fees
21 Dec - 22 Dec
Wayside Inn
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, (1000)
"Have stayed here multiple times -always good"
United States
Robert
The price is RM337
RM367 total
includes taxes & fees
11 Jan - 12 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1079)
Near Appleland Sports Centre and Kernstown Battlefield, this hotel offers a 24-hour fitness centre 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 RM402
RM438 total
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn & Suites Winchester
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 centre 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 RM1,222
RM1,335 total
includes taxes & fees
19 Jan - 20 Jan 2026
Glen Gordon Manor
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)
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 RM449
RM500 total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Front Royal
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)
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 RM399
RM440 total
includes taxes & fees
29 Dec - 30 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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)
Situated near Wayside Theatre and Cedar Creek National Historical Park, this hotel offers complimentary WiFi and parking. The 24-hour front desk ensures your needs are met anytime during your stay in this convenient Middletown location.
"I loved staying here!"
United States
Whitney
The price is RM254
RM280 total
includes taxes & fees
25 Dec - 26 Dec
Econo Lodge Inn & Suites Middletown - Winchester South
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, (1006)
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 RM253
RM282 total
includes taxes & fees
23 Dec - 24 Dec
Super 8 by Wyndham Front Royal
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, (917)
Located 5 minutes from Shenandoah National Park, this tranquil retreat offers a seasonal outdoor pool and on-site 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 RM226
RM251 total
includes taxes & fees
25 Dec - 26 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
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 RM482
RM540 total
includes taxes & fees
23 Dec - 24 Dec
TownePlace Suites by Marriott Front Royal
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 RM253
RM282 total
includes taxes & fees
31 Dec - 1 Jan 2026
Twi-Lite Inn
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)
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
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 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 RM278
RM309 total
includes taxes & fees
31 Dec - 1 Jan 2026
Relax Inn Motel
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 RM257
RM286 total
includes taxes & fees
30 Dec - 31 Dec
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.
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Couldnt be happier with my stay. Check in was easy, rooms were clean and bed bug free, there was a fridge, coffee maker and microwave! Easy shampoo, conditioner, body wash dispenser in the shower, the kids LOVED the heated indoor pool! There is coffee and hot chocolate in the lobby available At ALL TIMES. The continental breakfast was top notch! Even had sausage gravy! And! 711 was right next door incase you forget your phone charger (guilty)! And if you just wanted a little late night relax without going anywhere, they have a cooler upfront with some high noons and other wines for purchase. I will definitely recommend and definitely go back!"
Eileen 2-night trip
Posted 4 days ago
Country Inn & Suites by Radisson, Winchester, VA

More cheap stays in Chester Gap

Hampton Inn & Suites Williamsburg-Richmond Rd.

Hampton Inn & Suites Williamsburg-Richmond Rd.

1880 Richmond Rd Williamsburg VA
The price is RM251 per night from 1 Jan to 2 Jan
RM251
RM290 total
1 Jan - 2 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,006 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 Country Inn & Suites by Radisson, Winchester, VA. 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 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.

Explore a world of travel with Expedia