Photo by Brian V. Rowe

Chester Gap Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chester Gap hotels

Ramada by Wyndham Strasburg/Shenandoah Valley
Welcome to our hotel lobby, featuring a spacious area with a reception desk and comfortable seating.

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.2 out of 10, Very Good, (1011)
"Great location off the highway, restaurant on site was very good, staff was friendly and quick check in"
The price is P4,103
P4,567 total
includes taxes & fees
Sep 1 - Sep 2
Ramada by Wyndham Strasburg/Shenandoah Valley
Holiday Inn Express Winchester South-Stephens City by IHG
Guests can check in at the hotel's prominent entrance, surrounded by ample parking.

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very Good, (762)
"Always great!"
The price is P4,653
P5,063 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Express Winchester South-Stephens City by IHG
Baymont by Wyndham Front Royal Near Shenandoah National Park
Enter through the double glass doors into a welcoming space.

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 star property
6.4 out of 10, (856)
"We had a great stay. Clean and staff was friendly "
The price is P3,411
P3,797 total
includes taxes & fees
Aug 10 - Aug 11
Baymont by Wyndham Front Royal Near Shenandoah National Park
Quality Inn Stephens City - Winchester South
Enjoy a convenient breakfast at the hotel's well-equipped breakfast bar, featuring a juice dispenser, bowls, and a coffee machine.

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very Good, (596)
"Great stay!"
The price is P4,111
P4,473 total
includes taxes & fees
Sep 1 - Sep 2
Quality Inn Stephens City - Winchester South
Econo Lodge Inn & Suites
Enjoy a warm and elegant dining experience in this inviting space with a high ceiling, chandelier, and comfortable seating.

Econo Lodge Inn & Suites

2.0 star property
5.6 out of 10, (284)
"Great place to sleep and its was very quiet. "
The price is P3,926
P4,330 total
includes taxes & fees
Aug 11 - Aug 12
Econo Lodge Inn & Suites
L'Auberge Provencale Inn & Restaurant
Relax on the covered porch with comfortable seating and a beautiful view of the surrounding yard.

L'Auberge Provencale Inn & Restaurant

4.0 star property
9.6 out of 10, Exceptional, (167)
"Beautiful historic property well maintained and on the way to Skyline Drive. Breakfast was divine!"
The price is P14,483
P15,975 total
includes taxes & fees
Aug 5 - Aug 6
L'Auberge Provencale Inn & Restaurant
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Enjoy dining at this stylish restaurant with a central bar, high-top tables, and cozy booths.

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1002)
"Fantastic stay, thanks!"
The price is P6,872
P7,754 total
includes taxes & fees
Aug 10 - Aug 11
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Hampton Inn Front Royal
Classic hotel exterior with a symmetrical facade, large windows, and a prominent entrance.

Hampton Inn Front Royal

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Great stay!"
The price is P6,392
P7,114 total
includes taxes & fees
Aug 17 - Aug 18
Hampton Inn Front Royal
Fairfield Inn & Suites Strasburg Shenandoah Valley
Welcome to Marriott, a hotel with a modern design and covered entrance.

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Everything was fine; nothing outstanding but nothing bad either. Good place for an overnight stay while traveling "
The price is P6,573
P7,315 total
includes taxes & fees
Aug 17 - Aug 18
Fairfield Inn & Suites Strasburg Shenandoah Valley
Hillside
Row of charming buildings with porches, each with a flag and hanging flower baskets.

Hillside

2.5 star property
9.0 out of 10, Wonderful, (955)
"Charming stay at Hillside! Clean rooms, friendly staff, and close to beautiful mountain views. Perfect spot for visiting Shenandoah and Luray Caverns. Great value and peaceful vibes!"
Hillside
TownePlace Suites by Marriott Front Royal
Relax by the fire pit surrounded by comfortable wicker sofas and chairs in a sheltered outdoor space.

TownePlace Suites by Marriott Front Royal

3.0 star property
9.6 out of 10, Exceptional, (520)
"Breakfast was awesome, hit coffee available all day, clean rooms and great staff!"
The price is P8,085
P8,918 total
includes taxes & fees
Aug 17 - Aug 18
TownePlace Suites by Marriott Front Royal
Super 8 by Wyndham Front Royal
Relax in our welcoming lobby, featuring a reception desk, comfortable seating area, and dining space.

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1000)
"Convenient to Skyline Drive in Shenandoah National Park."
The price is P4,188
P4,661 total
includes taxes & fees
Aug 5 - Aug 6
Super 8 by Wyndham Front Royal
White Moose Inn
Enjoy the open-plan living space with a dining area and outdoor seating area.

White Moose Inn

4.0 star property
9.8 out of 10, Exceptional, (139)
"Wonderful option if visiting inn at little Washington or other sites nearby. Just a bock from inn with very helpful staff,happy hour, full breakfast and clean comfortable accommodations "
White Moose Inn
Comfort Inn & Suites Winchester
Welcome to Comfort Inn & Suites, featuring a modern exterior with a brick and beige facade and a welcoming entrance.

Comfort Inn & Suites Winchester

2.5 star property
9.4 out of 10, Exceptional, (1003)
"Perfect stay for our family while on the road"
The price is P5,636
P6,132 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Winchester
Country Inn & Suites by Radisson, Winchester, VA
Cozy living room with a fireplace, wooden shelves, and a light-colored sofa.

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1004)
"Great place to stay!"
The price is P5,537
P6,024 total
includes taxes & fees
Aug 6 - Aug 7
Country Inn & Suites by Radisson, Winchester, VA
Twi-Lite Inn
Office building with a welcoming entrance and lush greenery.

Twi-Lite Inn

2.0 star property
8.2 out of 10, Very Good, (515)
"Good "
The price is P4,420
P4,920 total
includes taxes & fees
Aug 28 - Aug 29
Twi-Lite Inn
Glen Gordon Manor
Traditional home surrounded by a beautifully maintained garden and lush greenery.

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (89)
"The location is good."
The price is P15,064
P16,466 total
includes taxes & fees
Aug 17 - Aug 18
Glen Gordon Manor
The Foster Harris House
Stunning two-story house with a central entrance, double doors, and a charming front porch.

The Foster Harris House

2.0 star property
10.0 out of 10, Exceptional, (1)
"Lovely inn in a great location three course breakfast with one of the best scones I have eaten "
The price is P29,024
P31,288 total
includes taxes & fees
Aug 5 - Aug 6
The Foster Harris House
Relax Inn Motel
Welcome to Relax Inn, a motel with a brick exterior and upper-floor balcony.

Relax Inn Motel

2.0 star property
8.2 out of 10, Very Good, (238)
"Clean, quiet and convenient. Check in process was quick and easy, with the very friendly and helpful staff. I would absolutely stay here again."
The price is P3,606
P4,014 total
includes taxes & fees
Aug 5 - Aug 6
Relax Inn Motel
Motel 6 Front Royal, VA
Step into the hotel lobby, featuring a high ceiling and a staircase leading to the upper level. The reception desk is centrally located, surrounded by comfortable seating and framed informational posters.

Motel 6 Front Royal, VA

2.0 star property
6.8 out of 10, (481)
"This is a great location! "
The price is P3,838
P4,272 total
includes taxes & fees
Aug 5 - Aug 6
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.
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 popular sights like Shenandoah National Park as you discover the local area in Chester Gap.

See all hotels in Chester Gap
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
"Only issue I didn’t have bath towels in the room."
James 1-night trip
Posted 1 day ago
Fairfield Inn & Suites Strasburg Shenandoah Valley

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 Ramada by Wyndham Strasburg/Shenandoah Valley 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! 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 are some hotels with pools in Chester Gap?

The Hillside Motel: Offers free self parking, a seasonal outdoor pool, and complimentary wireless Internet access. Country Inn & Suites by Radisson, Winchester, VA and Hampton Inn Front Royal are two additional hotels that offer an onsite pool. View all hotels with pools in Chester Gap.

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.