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Hotels in Winchester Historic District

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25 Dec - 26 Dec
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26 Dec - 27 Dec
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26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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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, (1005)
"Great hotel!"
United States
CHARLES
The price is S$184
includes taxes & fees
4 Jan - 5 Jan, 2026
The George Washington Hotel, A Wyndham Grand Hotel
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 S$138
includes taxes & fees
31 Dec - 1 Jan, 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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, (1000)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is S$163
includes taxes & fees
11 Jan - 12 Jan, 2026
Hampton Inn Front Royal
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, (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 S$138
includes taxes & fees
29 Dec - 30 Dec
La Quinta Inn & Suites by Wyndham Winchester
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, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is S$150
includes taxes & fees
4 Jan - 5 Jan, 2026
SpringHill Suites by Marriott Winchester
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 S$252
includes taxes & fees
8 Jan - 9 Jan, 2026
Hillbrook Inn
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 S$172
includes taxes & fees
14 Jan - 15 Jan, 2026
The Inn at Charles Town - Hollywood Casino
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, (1084)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is S$135
includes taxes & fees
25 Jan - 26 Jan, 2026
Comfort Inn & Suites Winchester
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 Winchester Historic District
9.6 out of 10, Exceptional, (556)
"Very good overall experience."
United States
Douglas
The price is S$170
includes taxes & fees
31 Dec - 1 Jan, 2026
TownePlace Suites by Marriott Front Royal
Exterior
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
3.1 km from Winchester Historic District
9.0 out of 10, Wonderful, (800)
"Quick check in, clean room, friendly staff."
United States
Darcy
The price is S$129
includes taxes & fees
27 Dec - 28 Dec
Fairfield Inn & Suites by Marriott 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, (772)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is S$136
includes taxes & fees
4 Jan - 5 Jan, 2026
TRU By Hilton Winchester
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 S$118
includes taxes & fees
11 Jan - 12 Jan, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Terrace/patio
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
14.2 km from Winchester Historic District
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 S$324
includes taxes & fees
8 Jan - 9 Jan, 2026
L'Auberge Provencale Inn & Restaurant
Exterior
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Winchester Historic District
8.2 out of 10, Very good, (540)
"Great pool and quiet area to stay in"
United States
Matthew
The price is S$89
includes taxes & fees
31 Dec - 1 Jan, 2026
Twi-Lite Inn
Restaurant
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 S$149
includes taxes & fees
2 Jan - 3 Jan, 2026
Courtyard by Marriott 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 S$225
includes taxes & fees
8 Jan - 9 Jan, 2026
The Carriage Inn B&B
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, (849)
"Super friendly reception and perfectly clean room. "
United States
Dwight
The price is S$154
includes taxes & fees
31 Dec - 1 Jan, 2026
Hampton Inn Winchester N/Conference Center, VA
Lift
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, (1001)
"Breakfast was delicious "
United States
Robert
The price is S$102
includes taxes & fees
1 Jan - 2 Jan, 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
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 S$115
includes taxes & fees
25 Jan - 26 Jan, 2026
Country Inn & Suites by Radisson, Winchester, VA
Exterior
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
24.8 km from Winchester Historic District
9.0 out of 10, Wonderful, (1000)
"Great stay."
United States
Kenneth
The price is S$161
includes taxes & fees
8 Jan - 9 Jan, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
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 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
"Goooood"
Doris 1-night trip
Posted 19 hours 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.

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