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19 Dec - 20 Dec
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Our top choices for Old Town Winchester hotels

2 restaurants, breakfast, lunch, dinner served; American cuisine
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 3.333.935 ₫
3.777.348 ₫ total
includes taxes & fees
28 Dec - 29 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Restaurant
Hampton Inn Martinsburg South-Inwood

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, (643)
"Professional staff clean rooms"
United States
Sandra
The price is 2.244.911 ₫
2.514.301 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Martinsburg South-Inwood
Exterior
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
24.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1001)
"Great stay."
United States
Kenneth
The price is 2.662.673 ₫
2.963.555 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Fairfield Inn & Suites Strasburg Shenandoah Valley
Lift
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
25.8 km from Old Town Winchester
8.4 out of 10, Very good, (1004)
"Breakfast was delicious "
United States
Robert
The price is 1.902.415 ₫
2.117.388 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
Restaurant
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 2.662.673 ₫
2.896.989 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Courtyard by Marriott Winchester
Property amenity
Holiday Inn Express Hotel & Suites Winchester by IHG

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, (801)
"Clean room, easy and quick check in."
United States
Jacqueline
The price is 2.869.316 ₫
3.121.815 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Express Hotel & Suites Winchester by IHG
Pillow-top beds, desk, laptop workspace, blackout curtains
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, (787)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is 2.662.673 ₫
2.896.989 ₫ total
includes taxes & fees
28 Dec - 29 Dec
SpringHill Suites by Marriott Winchester
Terrace/patio
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
14.1 km from Old Town Winchester
9.6 out of 10, Exceptional, (174)
"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
The price is 6.554.676 ₫
7.229.807 ₫ total
includes taxes & fees
21 Dec - 22 Dec
L'Auberge Provencale Inn & Restaurant
Lobby
Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal

Super 8 by Wyndham Front Royal
2.0 star property
30.4 km from Old Town Winchester
7.6 out of 10, Good, (1001)
"The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park."
United States
Teresa
The price is 1.632.088 ₫
1.816.619 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Super 8 by Wyndham Front Royal
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)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is 2.158.568 ₫
2.427.599 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Premium bedding, pillow-top beds, desk, blackout curtains
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)
"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 1.733.699 ₫
1.959.080 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Charles Town/Harpers Ferry
Lobby
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, (1000)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is 2.892.481 ₫
3.219.331 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Front Royal
Property entrance
Baymont by Wyndham Front Royal Near Shenandoah National Park

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, (919)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is 1.454.401 ₫
1.618.748 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Baymont by Wyndham Front Royal Near Shenandoah National Park
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 2.568.696 ₫
2.833.272 ₫ total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Property amenity
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
24.4 km from Old Town Winchester
9.6 out of 10, Exceptional, (554)
"Perfect for one night stay before Skyline Drive trip. "
United States
Timothy
The price is 3.106.232 ₫
3.478.821 ₫ total
includes taxes & fees
24 Dec - 25 Dec
TownePlace Suites by Marriott Front Royal
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 1.991.411 ₫
2.166.655 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn Winchester
Exterior
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very good, (540)
"Great pool and quiet area to stay in"
United States
Matthew
The price is 1.632.088 ₫
1.816.619 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Twi-Lite Inn
Suite, 1 Bedroom | 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 2.053.272 ₫
2.233.960 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester by IHG
Property amenity
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 4.185.516 ₫
5.345.878 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hillbrook Inn
Exterior
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, (2227)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is 2.600.811 ₫
2.829.682 ₫ total
includes taxes & fees
23 Dec - 24 Dec
La Quinta Inn & Suites by Wyndham 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

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.