Photo by Tina McClelland

Search Hotels in Winchester Historic District, Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester Historic District 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
Winchester Historic District
9.4 out of 10, Exceptional, (1007)
"Great hotel!"
United States
CHARLES
The price is 3.331.782 ₫
3.774.908 ₫ total
includes taxes & fees
21 Dec - 22 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
4.2 km from Winchester Historic District
9.2 out of 10, Wonderful, (1378)
"Excellent accommodations"
United States
Loretta
The price is 1.873.058 ₫
2.037.886 ₫ total
includes taxes & fees
4 Jan - 5 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 Winchester Historic District
9.0 out of 10, Wonderful, (766)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is 1.873.058 ₫
2.037.887 ₫ total
includes taxes & fees
5 Jan - 6 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 Winchester Historic District
9.4 out of 10, Exceptional, (1075)
"Very clean, helpful staff"
United States
Kathleen
The price is 2.580.454 ₫
2.807.534 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn & Suites Winchester
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
29.7 km from Winchester Historic District
8.0 out of 10, Very good, (1003)
"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 1.732.579 ₫
1.957.815 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Charles Town/Harpers Ferry
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
3 km from Winchester Historic District
9.2 out of 10, Wonderful, (2223)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is 2.674.107 ₫
2.909.428 ₫ total
includes taxes & fees
12 Jan - 13 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
2.1 km from Winchester Historic District
9.0 out of 10, Wonderful, (1002)
"Great location close to restaurants "
United States
SILVIA
The price is 1.978.286 ₫
2.241.356 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Spark by Hilton Winchester
Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
29.4 km from Winchester Historic District
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
The price is 3.409.387 ₫
3.852.607 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Carriage Inn B&B
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25.1 km from Winchester Historic District
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 2.820.110 ₫
3.138.783 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Front Royal
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 Winchester Historic District
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is 2.198.213 ₫
2.391.656 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
2 bars/lounges, sports bar
Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
29.9 km from Winchester Historic District
8.6 out of 10, Excellent, (1005)
"Certainly will stay again "
United States
philip
The price is 1.676.808 ₫
1.894.792 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Rodeway Inn & Suites Charles Town
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
3.3 km from Winchester Historic District
9.0 out of 10, Wonderful, (1003)
"Clean room, quiet area, good breakfast"
United States
Laurie
The price is 1.841.490 ₫
2.082.462 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
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
30.2 km from Winchester Historic District
8.6 out of 10, Excellent, (523)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is 3.419.647 ₫
4.093.106 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
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 Winchester Historic District
7.6 out of 10, Good, (1005)
"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 1.631.034 ₫
1.815.446 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Super 8 by Wyndham Front Royal
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 Winchester Historic District
9.4 out of 10, Exceptional, (779)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is 2.817.480 ₫
3.065.417 ₫ total
includes taxes & fees
21 Dec - 22 Dec
SpringHill Suites by Marriott Winchester
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
12.5 km from Winchester Historic District
8.2 out of 10, Very good, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is 1.946.718 ₫
2.118.029 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Holiday Inn Express Winchester South-Stephens City 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
22 km from Winchester Historic District
9.0 out of 10, Wonderful, (1002)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is 2.567.037 ₫
2.831.440 ₫ total
includes taxes & fees
15 Dec - 16 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Property amenity
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.8 km from Winchester Historic District
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 4.182.813 ₫
5.342.424 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Hillbrook Inn
Snack bar
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
2.3 km from Winchester Historic District
9.2 out of 10, Wonderful, (846)
"Super friendly reception and perfectly clean room. "
United States
Dwight
The price is 2.714.882 ₫
3.075.962 ₫ total
includes taxes & fees
20 Dec - 21 Dec
Hampton Inn Winchester N/Conference Center, VA
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
3.3 km from Winchester Historic District
8.8 out of 10, Excellent, (544)
"Very clean room, excellent staff!!!"
United States
James
The price is 2.051.946 ₫
2.232.516 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester by IHG
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.
View all properties

Where to stay in Winchester Historic District

Find the best Winchester Historic District areas for the activities you enjoy most.

Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

Top Winchester Historic District Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Winchester Historic District?
Travellers will be sure to enjoy their time in Winchester's Winchester Historic District neighbourhood. Make sure that you visit Bright Box Theater and Shenandoah Valley Discovery Museum as part of your Winchester Historic District travel plans.
How many hotels will I find in Winchester Historic District?
When you want to put your feet up after a day of exploring the sights in Winchester, you can choose from 17 Expedia hotels and other accommodation options in Winchester Historic District.
If I need to cancel my hotel reservation in Winchester Historic District, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of your booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to view the top deals on offer in Winchester Historic District.
What is there to do around this Winchester neighbourhood?
For cultural attractions in Winchester Historic District, head to Bright Box Theater, Old Court House Civil War Museum and Winchester Little Theater. You could also plan a visit to Shenandoah Valley Discovery Museum or Handley Regional Library while you're in the neighbourhood. A few places to visit in the area around Winchester Historic District include George Washington's Office, Stonewall Jackson's Headquarters and Mt Hebron Cemetery. While you're out sightseeing, Patsy Cline Historic House and Museum of the Shenandoah Valley are a couple of additional sights to visit in Winchester.