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Our top choices for Chester Gap hotels

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175 reviews)
"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 CA $261
CA $288 total
includes taxes & fees
Mar 11 - Mar 12
L'Auberge Provencale Inn & Restaurant

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very good, (1,000 reviews)
"Great stay everyone friendly will stay again"
United States
Mary K
The price is CA $104
CA $116 total
includes taxes & fees
Mar 6 - Mar 7
Ramada by Wyndham Strasburg/Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
Strasburg
9.0 out of 10, Wonderful, (1,000 reviews)
"We stay here every year on our way to NC. Always very nice and helpful staff."
United States
Catherine
The price is CA $154
CA $172 total
includes taxes & fees
Feb 26 - Feb 27
Fairfield Inn & Suites Strasburg Shenandoah Valley

The Foster Harris House

The Foster Harris House
2.0 star property
Washington
10.0 out of 10, Exceptional, (4 reviews)
"Lovely inn in a great location three course breakfast with one of the best scones I have eaten "
United States
Mary
The price is CA $680
CA $734 total
includes taxes & fees
Feb 26 - Feb 27
The Foster Harris House

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (151 reviews)
"Super friendly staff. The hotel is nice, cozy and very clean."
United States
Alejandra
White Moose Inn

Hillside

Hillside
2.5 star property
Luray
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean, spacious, would recommend"
United States
Noemi
Hillside

Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
The price is CA $490
CA $528 total
includes taxes & fees
Mar 11 - Mar 12
Gay Street Inn

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (422 reviews)
"Room 14 was great for spirit activity as well as the rest of the property! Highly recommend ghost hunters to explore the inn. Food at their Larick’s tavern was delish!! Overall service and staff were knowledgeable and friendly! We had a great experience for our anniversary! "
United States
Megan
The price is CA $98
CA $122 total
includes taxes & fees
Feb 19 - Feb 20
Wayside Inn

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, (1,001 reviews)
"Courteous staff, clean room. Nice to have free breakfast available."
Canada
Mary
The price is CA $116
CA $126 total
includes taxes & fees
Feb 26 - Feb 27
Country Inn & Suites by Radisson, Winchester, VA

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (96 reviews)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
The price is CA $435
CA $475 total
includes taxes & fees
Mar 16 - Mar 17
Glen Gordon Manor

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,101 reviews)
"Staff was very friendly and room was great! "
United States
Courtney
The price is CA $135
CA $147 total
includes taxes & fees
Feb 22 - Feb 23
Comfort Inn & Suites Winchester

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
"Very nice breakfast (eggs sausage, potatoes, ...), clean lobby, and all the staff was friendly, including Beatrix. Also we appreciated the attention to a clean and warm pool room on a very cold January. Great mexican 1 mile away at Potrillo's."
United States
kenneth
The price is CA $133
CA $148 total
includes taxes & fees
Mar 15 - Mar 16
Hampton Inn Front Royal

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, (1,000 reviews)
"The staff was friendly and very helpful! The room was spotless and very clean. Would stay at this location again :)"
United States
Stephanie
The price is CA $133
CA $147 total
includes taxes & fees
Mar 15 - Mar 16
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South
2.0 star property
Middletown
5.8 out of 10, (300 reviews)
"I loved staying here!"
United States
Whitney
The price is CA $85
CA $93 total
includes taxes & fees
Feb 26 - Feb 27
Econo Lodge Inn & Suites Middletown - Winchester South

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,000 reviews)
"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 CA $85
CA $94 total
includes taxes & fees
Feb 22 - Feb 23
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (32 reviews)
"Great place. Good food, great beer."
United States
Phil
Hopkins Ordinary Bed Breakfast and Ale Works

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
Front Royal
9.6 out of 10, Exceptional, (562 reviews)
"Clean room, friendly and helpful staff, good breakfast, I would stay again."
United States
Catherine
The price is CA $155
CA $174 total
includes taxes & fees
Feb 22 - Feb 23
TownePlace Suites by Marriott Front Royal

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, (929 reviews)
"Nice staff "
United States
Anthony
The price is CA $79
CA $88 total
includes taxes & fees
Feb 26 - Feb 27
Baymont by Wyndham Front Royal Near Shenandoah National Park

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very good, (545 reviews)
"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 CA $85
CA $94 total
includes taxes & fees
Feb 21 - Feb 22
Twi-Lite Inn

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very good, (260 reviews)
"Clean, and nice rooms, friendly staff"
United States
James
The price is CA $85
CA $94 total
includes taxes & fees
Feb 22 - Feb 23
Relax Inn 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.
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Learn more about Chester Gap

Check out popular sights like Shenandoah National Park as you discover the local area in Chester Gap.

Many butterflies
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Chester Gap Hotel Reviews

Recent Reviews in Chester Gap

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Hotels in Chester Gap with star rating

Frequently asked questions

What is the best area to stay in Chester Gap?
The best area to stay in Chester Gap is near the intersection of Route 522 and Route 66, which offers convenient access to the surrounding attractions.

This area is ideal for those looking to explore the natural beauty of the region, particularly for couples or small groups seeking a tranquil escape with easy access to outdoor activities. You'll find a selection of comfortable lodges and guesthouses located among the rolling hills, providing a peaceful base.

For couples, staying close to the Shenandoah National Park entrance, just a short drive from this intersection, is perfect. It allows for effortless day trips to scenic overlooks along Skyline Drive, hiking trails like those leading to Compton Peak, and opportunities for wildlife spotting. The area also boasts several local wineries, offering a relaxed way to spend an afternoon.

Families might prefer accommodations that offer a bit more space and perhaps some amenities like outdoor areas for children to play.
When is the best time to go to Chester Gap?
The best time to visit Chester Gap is during the late spring or autumn months.

Late spring, from April to May, offers pleasant temperatures and blooming wildflowers, making it ideal for outdoor activities like hiking and exploring the scenic beauty of the Blue Ridge Mountains. The weather is generally mild, superb for enjoying the local vineyards and orchards before the peak summer heat.

Autumn, particularly from September to October, is another excellent time to visit. The cooler temperatures and stunning fall foliage transform the landscape into a colourful spectacle, attracting many visitors for scenic drives and photography. This period is also popular for harvest festivals at local farms and wineries.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester Gap.
How can I save on a Chester Gap hotel booking with Expedia?
Members always get our best prices. Find our best Chester Gap hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Chester Gap hotel?
Prices for hotels in Chester Gap often vary, but you can find a great deal from CA $88 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.