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Winchester Historic District Hotels near Winchester

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

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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 P7,438
P8,428 total
includes taxes & fees
Jan 1 - Jan 2, 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 P5,731
P6,321 total
includes taxes & fees
Jan 4 - Jan 5, 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 P6,694
P7,451 total
includes taxes & fees
Jan 18 - Jan 19, 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 P5,803
P6,313 total
includes taxes & fees
Dec 29 - Dec 30
La Quinta Inn & Suites by Wyndham Winchester
Pillowtop beds, desk, laptop workspace, blackout drapes
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 P6,290
P6,844 total
includes taxes & fees
Jan 4 - Jan 5, 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 P9,338
P11,927 total
includes taxes & fees
Jan 8 - Jan 9, 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 P7,047
P8,480 total
includes taxes & fees
Jan 12 - Jan 13, 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 P5,664
P6,162 total
includes taxes & fees
Jan 25 - Jan 26, 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 P6,930
P7,762 total
includes taxes & fees
Dec 30 - Dec 31
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 P5,442
P5,920 total
includes taxes & fees
Dec 28 - Dec 29
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 P5,731
P6,235 total
includes taxes & fees
Jan 4 - Jan 5, 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 P4,816
P5,416 total
includes taxes & fees
Jan 16 - Jan 17, 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, (175)
"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 P13,450
P14,835 total
includes taxes & fees
Jan 4 - Jan 5, 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 P3,648
P4,061 total
includes taxes & fees
Dec 28 - Dec 29
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 P6,284
P6,837 total
includes taxes & fees
Jan 1 - Jan 2, 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 P9,895
P11,182 total
includes taxes & fees
Jan 8 - Jan 9, 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 P6,213
P7,039 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn Winchester N/Conference Center, VA
Elevator
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 P4,193
P4,667 total
includes taxes & fees
Jan 1 - Jan 2, 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 P4,832
P5,258 total
includes taxes & fees
Jan 25 - Jan 26, 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 P6,637
P7,387 total
includes taxes & fees
Jan 8 - Jan 9, 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 and neighborhoods for the activities you enjoy most.

Old Town Winchester

Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

Top Winchester Historic District Hotel Reviews

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

10/10 Excellent
"Checked in 11pm. The staff were welcoming and friendly. Room is clean. Breakfast was simple but sufficient. "
Tan Leng 1-night trip
Posted 1 day ago
Sleep Inn & Suites Winchester near University

Frequently asked questions

What's it like in Winchester Historic District?
Travelers will be sure to enjoy their time in Winchester's Winchester Historic District neighborhood. Be sure to check out 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 can I expect to find in Winchester Historic District?
When you want to kick up your feet after a day of exploring the sights in Winchester, you can choose from 16 Expedia hotels and other accommodations in Winchester Historic District.
If I need to cancel my hotel reservation in Winchester Historic District, will I receive a refund?
Yes! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Add dates, click "Search", then you can filter by "fully refundable" to review top deals in Winchester Historic District.
What is there to do around this Winchester neighborhood?
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 neighborhood. 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.