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Hotels in Old Town Winchester, Winchester

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 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, (1011)
"Great hotel!"
United States
CHARLES
The price is RM518
RM587 total
includes taxes & fees
22 Dec - 23 Dec
The George Washington Hotel, A Wyndham Grand Hotel
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, (770)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is RM291
RM317 total
includes taxes & fees
9 Jan - 10 Jan 2026
TRU By Hilton Winchester
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, (1077)
"Very clean, helpful staff"
United States
Kathleen
The price is RM405
RM440 total
includes taxes & fees
12 Jan - 13 Jan 2026
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, (523)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is RM491
RM591 total
includes taxes & fees
17 Dec - 18 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 RM651
RM831 total
includes taxes & fees
12 Jan - 13 Jan 2026
Hillbrook Inn
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, (1000)
"The room is clean. The staff is friendly. The breakfast was good. No-frills hotel, but clean and efficient. "
United States
Kelsey
The price is RM270
RM305 total
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Charles Town/Harpers Ferry
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, (1007)
"Certainly will stay again "
United States
philip
The price is RM261
RM295 total
includes taxes & fees
4 Jan - 5 Jan 2026
Rodeway Inn & Suites Charles Town
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, (1382)
"Clean nice room with a hot breakfast, a lot nicer then other places in Winchester especially for the price. Highly recommend "
United States
Curtis
The price is RM305
RM331 total
includes taxes & fees
31 Dec - 1 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
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, (2226)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is RM420
RM457 total
includes taxes & fees
4 Jan - 5 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, (1003)
"Great location close to restaurants "
United States
SILVIA
The price is RM308
RM349 total
includes taxes & fees
11 Jan - 12 Jan 2026
Spark 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, (1004)
"Have stayed here multiple times -always good"
United States
Robert
The price is RM343
RM373 total
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
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, (1005)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is RM287
RM324 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
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 RM439
RM489 total
includes taxes & fees
25 Dec - 26 Dec
Hampton Inn Front Royal
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
9.4 out of 10, Exceptional, (782)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is RM438
RM477 total
includes taxes & fees
21 Dec - 22 Dec
SpringHill Suites by Marriott Winchester
Front of property
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
29.3 km from Old Town Winchester
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is RM530
RM599 total
includes taxes & fees
30 Dec - 31 Dec
The Carriage Inn B&B
In-room safe, desk, laptop workspace, blackout curtains
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
3.1 km from Old Town Winchester
8.8 out of 10, Excellent, (544)
"Very clean room, excellent staff!!!"
United States
James
The price is RM319
RM347 total
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester by IHG
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, (1003)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is RM399
RM441 total
includes taxes & fees
23 Dec - 24 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1003)
"Great stay"
United States
Jaron
The price is RM310
RM337 total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn Winchester
Exterior
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
3.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (915)
"comfortable room, amenities and staff"
United States
Prashant
The price is RM438
RM476 total
includes taxes & fees
23 Dec - 24 Dec
Courtyard by Marriott 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, (798)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is RM379
RM413 total
includes taxes & fees
18 Dec - 19 Dec
Fairfield Inn & Suites by Marriott Winchester
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Yes"
Mark 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Winchester

Explore a world of travel with Expedia

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.
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 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.