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12 Dec - 13 Dec
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13 Dec - 14 Dec
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12 Dec - 14 Dec
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Our top choices for Old Town Winchester hotels

Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1006)
"Great hotel!"
United States
CHARLES
The price is 3.338.114 ₫
3.782.083 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
4.1 km from Old Town Winchester
9.2 out of 10, Wonderful, (1377)
"Excellent accommodations"
United States
Loretta
The price is 1.916.751 ₫
2.085.426 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.0 out of 10, Wonderful, (766)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is 1.874.625 ₫
2.039.593 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
TRU By Hilton 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
7.5 km from Old Town Winchester
8.8 out of 10, Excellent, (1001)
"Have stayed here multiple times -always good"
United States
Robert
The price is 2.220.061 ₫
2.415.427 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
2.9 km from Old Town Winchester
9.2 out of 10, Wonderful, (2222)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is 2.704.228 ₫
2.942.200 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
La Quinta Inn & Suites by Wyndham Winchester
Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1002)
"Great location close to restaurants "
United States
SILVIA
The price is 1.979.941 ₫
2.243.231 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Spark by Hilton Winchester
2 bars/lounges, sports bar
Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
29.7 km from Old Town Winchester
8.6 out of 10, Excellent, (1004)
"Good for me and front desk allowed me to check in early"
United States
Devan
The price is 1.678.210 ₫
1.896.376 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Rodeway Inn & Suites Charles Town
Lobby
Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
29.6 km from Old Town Winchester
8.0 out of 10, Very good, (1001)
"Nice place to stay"
United States
Cynthia
The price is 1.734.028 ₫
1.959.450 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Charles Town/Harpers Ferry
Exterior
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
5.3 km from Old Town Winchester
9.6 out of 10, Exceptional, (777)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is 2.819.836 ₫
3.067.983 ₫ total
includes taxes & fees
28 Dec - 29 Dec
SpringHill Suites by Marriott Winchester
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
3.2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1002)
"Clean room, quiet area, good breakfast"
United States
Laurie
The price is 1.843.030 ₫
2.084.204 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
7.8 km from Old Town Winchester
9.4 out of 10, Exceptional, (1073)
"Very clean, helpful staff"
United States
Kathleen
The price is 2.626.318 ₫
2.857.434 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Comfort Inn & Suites Winchester
Restaurant
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
30 km from Old Town Winchester
8.6 out of 10, Excellent, (521)
"the room was clean and the staff was great. The shuttle service to the casino was awesome."
United States
Steve
The price is 3.422.507 ₫
4.096.529 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Front of property
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is 4.186.311 ₫
5.346.894 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Hillbrook Inn
Exterior
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1001)
"Great stay"
United States
Jaron
The price is 1.991.789 ₫
2.167.065 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Quality Inn Winchester
Lobby
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
2.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (797)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is 2.439.382 ₫
2.654.047 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites by Marriott Winchester
Indoor pool
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1002)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is 2.822.469 ₫
3.141.407 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hampton Inn Front Royal
Lobby
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
2.9 km from Old Town Winchester
8.6 out of 10, Excellent, (1081)
"Good price, good location "
United States
George
The price is 1.790.372 ₫
1.947.819 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Travelodge by Wyndham Winchester
Reception
TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
3 km from Old Town Winchester
8.8 out of 10, Excellent, (478)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is 2.819.836 ₫
3.067.981 ₫ total
includes taxes & fees
15 Dec - 16 Dec
TownePlace Suites by Marriott Winchester
Lobby sitting area
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
3.1 km from Old Town Winchester
7.8 out of 10, Good, (1002)
"great stay with breakfast too"
United States
James
The price is 1.797.218 ₫
1.955.373 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites Winchester near University
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
21.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is 2.569.184 ₫
2.833.809 ₫ total
includes taxes & fees
18 Dec - 19 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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 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 Shenandoah Valley Discovery Museum.

Top Old Town Winchester Hotel Reviews

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Frequently asked questions

What is Old Town Winchester like?
Old Town Winchester is an historic neighbourhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Make sure that you visit Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighbourhood.
How many hotels should I expect to find in the Old Town Winchester area?
With 12 Expedia hotels and other accommodation options 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, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to review the best deals available in Old Town Winchester.
What is there to do around this Winchester neighbourhood?
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 worth a visit in the neighbourhood. 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.