Old Town Winchester Hotels, Winchester

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6 Dec - 7 Dec
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19 Dec - 21 Dec

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366 Cheap Hotels in Old Town Winchester - Specials, Reviews, & Last Minute Deals

2 restaurants, breakfast, lunch, dinner served; American cuisine
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)
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
United States
Jeanette
The price is AU$216
includes taxes & fees
14 Dec - 15 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Exterior
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, (2215)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is AU$171
includes taxes & fees
16 Dec - 17 Dec
La Quinta Inn & Suites by Wyndham Winchester
Snack bar
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, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is AU$121
includes taxes & fees
5 Jan - 6 Jan 2026
TRU By Hilton Winchester
Exterior
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, (1004)
"Clean room, nicely furnished."
United States
Marilyn
The price is AU$126
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

3.0 star property
2.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (507)
"Great hotel"
United States
DONNA D
The price is AU$163
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Winchester
Restaurant
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, (517)
"Staff was courteous….helpful…room was clean and comfortable "
United States
David
The price is AU$217
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Exterior
Quality Inn Winchester

Quality Inn Winchester

2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1006)
"Great stay"
United States
Jaron
The price is AU$124
includes taxes & fees
14 Dec - 15 Dec
Quality Inn Winchester
Lobby
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, (1076)
"Good price, good location "
United States
George
The price is AU$111
includes taxes & fees
14 Dec - 15 Dec
Travelodge by Wyndham Winchester
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

2.5 star property
12.4 km from Old Town Winchester
8.2 out of 10, Very good, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is AU$121
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Winchester South-Stephens City by IHG
Suite, 1 Bedroom
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, (542)
"Very clean room, excellent staff!!!"
United States
James
The price is AU$128
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester by IHG
Lift
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 star property
25.8 km from Old Town Winchester
8.2 out of 10, Very good, (1004)
"Friendly Staff, clean room."
Canada
Frank
The price is AU$120
includes taxes & fees
23 Dec - 24 Dec
Ramada by Wyndham Strasburg/Shenandoah Valley
Restaurant
Hampton Inn Martinsburg South-Inwood

Hampton Inn Martinsburg South-Inwood

2.5 star property
22.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (642)
"Good location "
United States
Judith
The price is AU$140
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Martinsburg South-Inwood
Lobby
Spark by Hilton Winchester

Spark by Hilton Winchester

3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1001)
"Great location close to restaurants "
United States
SILVIA
The price is AU$136
includes taxes & fees
5 Jan - 6 Jan 2026
Spark by Hilton Winchester
Exterior
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 AU$152
includes taxes & fees
11 Dec - 12 Dec
Fairfield Inn & Suites by Marriott Winchester
Property amenity
Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG

2.5 star property
3.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (798)
"Clean room, easy and quick check in."
United States
Jacqueline
The price is AU$170
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Express Hotel & Suites Winchester by IHG
Property entrance
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 star property
29.8 km from Old Town Winchester
6.4 out of 10, (916)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is AU$90
includes taxes & fees
23 Dec - 24 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
Lobby
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, (1371)
"Excellent accommodations"
United States
Loretta
The price is AU$119
includes taxes & fees
5 Jan - 6 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
Restaurant
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, (911)
"comfortable room, amenities and staff"
United States
Prashant
The price is AU$175
includes taxes & fees
13 Dec - 14 Dec
Courtyard by Marriott Winchester
2 bars/lounges, sports bar
Rodeway Inn & Suites - Charles Town, WV

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
29.7 km from Old Town Winchester
8.6 out of 10, Excellent, (1001)
"I loved how clean the hotel was the check-in process was easy and even the people working upfront or super nice."
United States
Paul
The price is AU$108
includes taxes & fees
21 Dec - 22 Dec
Rodeway Inn & Suites - Charles Town, WV
Breakfast area
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.0 star property
19.3 km from Old Town Winchester
5.8 out of 10, (299)
"I loved staying here!"
United States
Whitney
The price is AU$103
includes taxes & fees
14 Dec - 15 Dec
Econo Lodge Inn & Suites
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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Our guide on 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

Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"Again, this hotel is great! The staff is amazing and very accommodating. The hotel is very clean and comforting. I will stay here again! "
Tyeshia 2-night trip
Posted 7 days ago
Hampton Inn Front Royal

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.

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