Photo by Brian V. Rowe

Find hotels in Chester Gap, VA from $61

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Our top choices for Chester Gap hotels

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1101)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
$98 nightly
The price is $107
Jan 11 - Jan 12
Total with taxes and fees
Comfort Inn & Suites Winchester

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, (1001)
"Clean efficient room with good front desk service. Convienence to Highway 81 and eateries."
United States
Chris
$83 nightly
The price is $90
Jan 25 - Jan 26
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
Strasburg
8.4 out of 10, Very Good, (1000)
"Staff was friendly, rooms were clean and area was nice"
United States
Meghan
$73 nightly
The price is $81
Jan 13 - Jan 14
Total with taxes and fees
Ramada by Wyndham Strasburg/Shenandoah Valley

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)
"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
$98 nightly
The price is $108
Jan 15 - Jan 16
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
Front Royal
9.0 out of 10, Wonderful, (1005)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
$98 nightly
The price is $109
Jan 13 - Jan 14
Total with taxes and fees
Hampton Inn Front Royal

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, (810)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
$74 nightly
The price is $81
Jan 11 - Jan 12
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG

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, (1001)
"Good condition "
United States
Phillip
$62 nightly
The price is $69
Jan 8 - Jan 9
Total with taxes and fees
Super 8 by Wyndham Front Royal Near Shenandoah National Park

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)
"Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants. "
United States
Carla
$112 nightly
The price is $123
Jan 11 - Jan 12
Total with taxes and fees
TownePlace Suites by Marriott Front Royal

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
Strasburg
9.0 out of 10, Wonderful, (1000)
"We like staying here on our way south."
United States
Catherine
$113 nightly
The price is $126
Jan 15 - Jan 16
Total with taxes and fees
Fairfield Inn & Suites Strasburg Shenandoah Valley

White Moose Inn

White Moose Inn
4.0 star property
Washington
9.8 out of 10, Exceptional, (149)
"Staff is wonderful. The whole 1st floor would make Marie Kondo proud! Breakfast is excellent. "
United States
Judy
$314 nightly
The price is $339
Feb 6 - Feb 7
Total with taxes and fees
White Moose Inn

Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (97)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
$289 nightly
The price is $316
Jan 20 - Jan 21
Total with taxes and fees
Glen Gordon Manor

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175)
"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
$220 nightly
The price is $243
Jan 8 - Jan 9
Total with taxes and fees
L'Auberge Provencale Inn & Restaurant

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
Front Royal
8.2 out of 10, Very Good, (544)
"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
$68 nightly
The price is $76
Jan 8 - Jan 9
Total with taxes and fees
Twi-Lite Inn

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)
"Good variety at breakfast and courteous staff."
Canada
Madonna
$75 nightly
The price is $82
Jan 25 - Jan 26
Total with taxes and fees
Quality Inn Stephens City - Winchester South

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, (925)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
$55 nightly
The price is $61
Jan 13 - Jan 14
Total with taxes and fees
Baymont by Wyndham Front Royal Near Shenandoah National Park

Relax Inn Motel

Relax Inn Motel
2.0 star property
Front Royal
8.2 out of 10, Very Good, (259)
"Clean, and nice rooms, friendly staff"
United States
James
$68 nightly
The price is $76
Jan 8 - Jan 9
Total with taxes and fees
Relax Inn Motel

Wayside Inn

Wayside Inn
3.5 star property
Middletown
9.2 out of 10, Wonderful, (419)
"Historic inn. "
United States
Anonymous traveler
$89 nightly
The price is $98
Jan 8 - Jan 9
Total with taxes and fees
Wayside Inn

Hillside

Hillside
2.5 star property
Luray
9.0 out of 10, Wonderful, (1003)
"Clean, spacious, would recommend"
United States
Noemi
$123 nightly
The price is $142
Jan 11 - Jan 12
Total with taxes and fees
Hillside

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
Front Royal
6.8 out of 10, (503)
"Great Motel 6. Clean and near good restaurants. Large area for walking dogs"
United States
Chris
$58 nightly
The price is $65
Jan 18 - Jan 19
Total with taxes and fees
Motel 6 Front Royal, VA

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)
"Great place. Good food, great beer."
United States
Phil
$277 nightly
The price is $303
Jan 13 - Jan 14
Total with taxes and fees
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.
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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

More cheap stays in Chester Gap

Hotels in Chester Gap with star-rating

Frequently asked questions

When is the best time to go to Chester Gap?
The most popular time to visit Chester Gap is April, as the region bursts into bloom with vibrant wildflowers and mild weather. Temperatures during this month typically range from the mid-50s to low 70s Fahrenheit, creating an friendly space for outdoor adventures such as hiking, wine tasting, and exploring the beautiful countryside.

During the peak season from April to June, Chester Gap attracts many travelers eager to enjoy its scenic landscapes and charming local vineyards. This is an ideal time to embark on hiking trails in the nearby Blue Ridge Mountains, where you can soak in stunning vistas and fresh spring air. The pleasant climate also makes it superb for leisurely picnics and outdoor dining at local eateries that showcase the region's culinary delights.

For those seeking a more tranquil experience, late fall, particularly November, may present an attractive option. It offers a chance to appreciate the changing colors of the foliage while enjoying fewer crowds at popular attractions. Plus, this month often features harvest festivals, where you can savor locally produced wines and artisanal foods.
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?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Chester Gap hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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 $61 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.

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