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Winchester Historic District Hotels, Winchester

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Winchester Historic District 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
Winchester Historic District
9.4 out of 10, Exceptional, (1004)
"Great hotel!"
United States
CHARLES
The price is NZ$246
includes taxes & fees
5 Jan - 6 Jan 2026
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, (1398)
"Clean room great helpful staff good breakfast"
United States
Loretta
The price is NZ$147
includes taxes & fees
29 Dec - 30 Dec
Microtel Inn & Suites by Wyndham Winchester
Lobby
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
25.7 km from Winchester Historic District
8.4 out of 10, Very good, (1000)
"Breakfast was delicious "
United States
Robert
The price is NZ$137
includes taxes & fees
1 Jan - 2 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
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
3 km from Winchester Historic District
9.2 out of 10, Wonderful, (2234)
"The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. "
United States
Jordyn
The price is NZ$184
includes taxes & fees
29 Dec - 30 Dec
La Quinta Inn & Suites by Wyndham 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
29.9 km from Winchester Historic District
8.6 out of 10, Excellent, (1003)
"Certainly will stay again "
United States
philip
The price is NZ$123
includes taxes & fees
11 Jan - 12 Jan 2026
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
29.7 km from Winchester Historic District
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 NZ$128
includes taxes & fees
28 Dec - 29 Dec
Days Inn by Wyndham Charles Town/Harpers Ferry
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, (1002)
"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 NZ$118
includes taxes & fees
25 Dec - 26 Dec
Super 8 by Wyndham Front Royal
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, (772)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is NZ$182
includes taxes & fees
5 Jan - 6 Jan 2026
TRU By Hilton Winchester
Exterior
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, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is NZ$199
includes taxes & fees
11 Jan - 12 Jan 2026
SpringHill Suites by Marriott 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 Winchester Historic District
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is NZ$154
includes taxes & fees
18 Jan - 19 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Front of property
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 NZ$335
includes taxes & fees
8 Jan - 9 Jan 2026
Hillbrook Inn
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, (1090)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is NZ$181
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn & Suites 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)
"The place is spotless, comfortable and quiet. Very convenient as well, right off of 81"
United States
Michael
The price is NZ$159
includes taxes & fees
5 Jan - 6 Jan 2026
Spark by Hilton Winchester
Suite, 1 Bedroom
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, (546)
"Very clean room, excellent staff!!!"
United States
James
The price is NZ$146
includes taxes & fees
3 Jan - 4 Jan 2026
Candlewood Suites Winchester by IHG
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, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is NZ$158
includes taxes & fees
8 Jan - 9 Jan 2026
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, (526)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is NZ$242
includes taxes & fees
7 Jan - 8 Jan 2026
The Inn at Charles Town - Hollywood Casino
Exterior
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, (807)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is NZ$138
includes taxes & fees
4 Jan - 5 Jan 2026
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, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is NZ$184
includes taxes & fees
31 Dec - 1 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Exterior
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
2.9 km from Winchester Historic District
9.0 out of 10, Wonderful, (919)
"comfortable room, amenities and staff"
United States
Prashant
The price is NZ$199
includes taxes & fees
30 Dec - 31 Dec
Courtyard 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
3.2 km from Winchester Historic District
7.8 out of 10, Good, (1000)
"great stay with breakfast too"
United States
James
The price is NZ$115
includes taxes & fees
18 Jan - 19 Jan 2026
Sleep Inn & Suites Winchester near University
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

Our guide on 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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!"
David 1-night trip
Posted 2 days ago
Comfort Inn & Suites Winchester

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.
Where is the best hotel for a stay in Winchester Historic District?
Based on Expedia customer reviews, The George Washington Hotel, A Wyndham Grand Hotel is the highest ranked property in Winchester Historic District. This hotel offers a full-service spa and 2 restaurants.
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 16 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.