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Discover Old Town Winchester hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1006)
"Perfect location to visit for business or pleasure!"
The price is AED 465
AED 527 total
includes taxes & fees
9 Oct - 10 Oct
The George Washington Hotel, A Wyndham Grand Hotel

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
9.2 out of 10, Wonderful, (2165)
"Nicely renovated hotel with great room. "
The price is AED 398
AED 433 total
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Winchester

Candlewood Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (516)
"The suites we're clean and spacious. The perfect stay for a family weekend!"
The price is AED 342
AED 372 total
includes taxes & fees
6 Oct - 7 Oct
Candlewood Suites Winchester by IHG

Quality Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (1000)
"We will be staying there again"
The price is AED 278
AED 302 total
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Winchester

The Inn at Charles Town - Hollywood Casino

3.0 star property
8.6 out of 10, Excellent, (494)
"It is convenient to the casino and racetrack. The continental breakfast was average at best. For a tremendous breakfast try the Charlestown Family Diner across the street from this property."
The price is AED 441
AED 530 total
includes taxes & fees
3 Nov - 4 Nov
The Inn at Charles Town - Hollywood Casino

Holiday Inn Winchester Se-Historic Gateway by IHG

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great hotel! "
The price is AED 323
AED 363 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Winchester Se-Historic Gateway by IHG

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
8.4 out of 10, Very Good, (1004)
"Mexican restaurant on site was convenient after a long day of driving. "
The price is AED 256
AED 285 total
includes taxes & fees
2 Nov - 3 Nov
Ramada by Wyndham Strasburg/Shenandoah Valley

Travelodge by Wyndham Winchester

2.5 star property
8.4 out of 10, Very Good, (1104)
"My favorite hotel in VA, always stay there when visiting friends and family. "
The price is AED 253
AED 276 total
includes taxes & fees
2 Nov - 3 Nov
Travelodge by Wyndham Winchester

Fairfield Inn & Suites by Marriott Winchester

2.5 star property
9.0 out of 10, Wonderful, (772)
"This was a very clean well run hotel and the staff was friendly and accomodating. Would definitely stay here again."
The price is AED 340
AED 370 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Winchester

Travelodge By Wyndham Charles Town/Harpers Ferry

2.0 star property
7.0 out of 10, Good, (243)
"Wasn’t the cleanest but it’s good for a quick stop"
The price is AED 248
AED 280 total
includes taxes & fees
6 Oct - 7 Oct
Travelodge By Wyndham Charles Town/Harpers Ferry

Hampton Inn Martinsburg South-Inwood

2.5 star property
9.2 out of 10, Wonderful, (621)
"The property was very clean and the breakfast was excellent."
The price is AED 372
AED 416 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Martinsburg South-Inwood

Hampton Inn Winchester-University/Mall Area

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Price, Clean!,great breakfast, attention to details and nice room, loved it!"
The price is AED 391
AED 443 total
includes taxes & fees
13 Oct - 14 Oct
Hampton Inn Winchester-University/Mall Area

Hilton Garden Inn Winchester

3.0 star property
8.8 out of 10, Excellent, (494)
"A great stop for our family of four on a long drive home."
The price is AED 418
AED 474 total
includes taxes & fees
26 Oct - 27 Oct
Hilton Garden Inn Winchester

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 star property
6.4 out of 10, (887)
"nice for a great stay!!"
The price is AED 209
AED 233 total
includes taxes & fees
2 Nov - 3 Nov
Baymont by Wyndham Front Royal Near Shenandoah National Park

TRU By Hilton Winchester

2.5 star property
9.0 out of 10, Wonderful, (707)
"Clean decent size room, easy parking, not too far from highway, lots of traffic around but the room was very quiet"
The price is AED 375
AED 408 total
includes taxes & fees
2 Nov - 3 Nov
TRU By Hilton Winchester

Courtyard by Marriott Winchester

3.0 star property
8.8 out of 10, Excellent, (883)
" Nice hotel"
The price is AED 393
AED 428 total
includes taxes & fees
9 Oct - 10 Oct
Courtyard by Marriott Winchester

Spark by Hilton Winchester

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very dated. Very nice in common areas but rooms could use a renovation"
The price is AED 331
AED 375 total
includes taxes & fees
2 Nov - 3 Nov
Spark by Hilton Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
8.2 out of 10, Very Good, (773)
"Great stay!"
The price is AED 342
AED 372 total
includes taxes & fees
30 Oct - 31 Oct
Holiday Inn Express Winchester South-Stephens City by IHG

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
8.6 out of 10, Excellent, (1028)
"It is a very good place to stay "
The price is AED 268
AED 303 total
includes taxes & fees
2 Nov - 3 Nov
Rodeway Inn & Suites - Charles Town, WV

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very Good, (610)
"Great stay!"
The price is AED 280
AED 305 total
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Stephens City - Winchester South
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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Where to stay in Old Town Winchester

Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Top Old Town Winchester Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What is Old Town Winchester like?

Old Town Winchester is a historic neighborhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Be sure to check out Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighborhood.

Where is the best place to stay in Old Town Winchester?

Based on Expedia customer reviews, The George Washington Hotel, A Wyndham Grand Hotel is the highest ranked property in Old Town Winchester. This hotel offers a full-service spa and 2 restaurants.

How many hotels can I expect to find in the Old Town Winchester area?

With 12 Expedia hotels and other accommodations in Old Town Winchester to choose from, this is a good starting point for exploring the greater Winchester area.

If I need to cancel my hotel reservation in Old Town Winchester, will I receive a refund?

Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get top deals in Old Town Winchester.

Where can I learn more about changing or cancelling my trip to Old Town Winchester?

For additional details about rescheduling or cancelling your trip to Old Town Winchester, head over to our customer service page.

What is there to do around this Winchester neighborhood?

Sights like Bright Box Theater and Old Court House Civil War Museum can be part of your cultural tour of Old Town Winchester. Shenandoah Valley Discovery Museum and Handley Regional Library are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include George Washington's Office, Mt Hebron Cemetery, and Winchester Little Theater. When you're sightseeing in Winchester, Stonewall Jackson's Headquarters and Patsy Cline Historic House are also worth a stop.