Photo by Brian V. Rowe

Chester Gap Hotels

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
Jan 1 - Jan 2
Tomorrow
Jan 2 - Jan 3
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester Gap hotels

Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1093)
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.
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is P5,598
P6,090 total
includes taxes & fees
Jan 25 - Jan 26
Comfort Inn & Suites Winchester
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 P4,877
P5,307 total
includes taxes & fees
Jan 25 - Jan 26
Country Inn & Suites by Radisson, Winchester, VA
Elevator
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, (1004)
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.
"Breakfast was delicious "
United States
Robert
The price is P4,302
P4,788 total
includes taxes & fees
Jan 7 - Jan 8
Ramada by Wyndham Strasburg/Shenandoah Valley
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.
"Clean rooms and property. Staff was amazing. Hot tub and pool area were great and clean. Very comfortable stay. Only issue was shower was very slow to drain but confident staff will fix it for next"
United States
Edward
The price is P5,742
P6,334 total
includes taxes & fees
Jan 8 - Jan 9
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1001)
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.
"Good condition "
United States
Phillip
The price is P3,649
P4,061 total
includes taxes & fees
Jan 8 - Jan 9
Super 8 by Wyndham Front Royal
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, (809)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is P4,355
P4,738 total
includes taxes & fees
Jan 4 - Jan 5
Holiday Inn Express Winchester South-Stephens City by IHG
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, (1005)
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 P6,708
P7,465 total
includes taxes & fees
Jan 11 - Jan 12
Hampton Inn Front Royal
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, (558)
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.
"Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants. "
United States
Carla
The price is P6,944
P7,777 total
includes taxes & fees
Jan 6 - Jan 7
TownePlace Suites by Marriott Front Royal
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)
"Breakfast was great - they even had vegetarian sausage! Everything was clean, and staff were friendly and helpful."
United States
David
The price is P6,650
P7,401 total
includes taxes & fees
Jan 14 - Jan 15
Fairfield Inn & Suites Strasburg Shenandoah Valley
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 P4,002
P4,454 total
includes taxes & fees
Jan 2 - Jan 3
Relax Inn Motel
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, (175)
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 P13,476
P14,864 total
includes taxes & fees
Jan 4 - Jan 5
L'Auberge Provencale Inn & Restaurant
Exterior
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (95)
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 P17,037
P18,621 total
includes taxes & fees
Jan 20 - Jan 21
Glen Gordon Manor
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)
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 P4,327
P4,708 total
includes taxes & fees
Jan 25 - Jan 26
Quality Inn Stephens City - Winchester South
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, (924)
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 P3,251
P3,619 total
includes taxes & fees
Jan 7 - Jan 8
Baymont by Wyndham Front Royal Near Shenandoah National Park
Exterior
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very Good, (543)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is P4,002
P4,454 total
includes taxes & fees
Jan 4 - Jan 5
Twi-Lite Inn
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (419)
"Historic inn. "
United States
Anonymous traveler
The price is P4,237
P5,261 total
includes taxes & fees
Jan 4 - Jan 5
Wayside Inn
Terrace/patio
White Moose Inn

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (149)
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.
"Staff is wonderful. The whole 1st floor would make Marie Kondo proud! Breakfast is excellent. "
United States
Judy
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
Front of property
The Foster Harris House

The Foster Harris House

The Foster Harris House
2.0 star property
Washington
10.0 out of 10, Exceptional, (4)
Start your day with complimentary English breakfast at this Washington hotel, just a 15-minute drive from Shenandoah National Park. Free WiFi and parking add value, while Little Washington Theatre and local monuments await nearby.
"Lovely inn in a great location three course breakfast with one of the best scones I have eaten "
United States
Mary
The price is P29,365
P31,656 total
includes taxes & fees
Jan 2 - Jan 3
The Foster Harris House
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
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

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

10/10 Excellent
"Yes "
Paul 2-night trip
Posted 9 days ago
Fairfield Inn & Suites 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 P3,251 per night from Jan 7 to Jan 8
P3,251
P3,619 total
Jan 7 - Jan 8
includes taxes & fees
6.4/10 (920 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 traveler data. Other good options for your stay in the area are DoubleTree by Hilton Front Royal Blue Ridge Shadows and Hampton Inn Front Royal. 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.
What is staying in Chester Gap like?
Visitors to Chester Gap are sure to find plenty to explore and enjoy. 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.