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Find hotels in Winchester Historic District, Winchester

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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, (1010)
"Great hotel!"
United States
CHARLES
The price is ￥19,830
￥22,468 total
includes taxes & fees
Jan 4 - Jan 5, 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, (1001)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is ￥15,278
￥16,851 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, (1002)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is ￥17,846
￥19,861 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn Front Royal
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 ￥25,061
￥28,319 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Carriage Inn B&B
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, (530)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is ￥17,848
￥21,556 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Inn at Charles Town - Hollywood Casino
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 ￥35,139
￥38,758 total
includes taxes & fees
Jan 5 - Jan 6, 2026
L'Auberge Provencale Inn & Restaurant
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, (558)
"Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants. "
United States
Carla
The price is ￥18,475
￥20,691 total
includes taxes & fees
Jan 1 - Jan 2, 2026
TownePlace Suites by Marriott Front Royal
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 ￥16,769
￥18,245 total
includes taxes & fees
Jan 4 - Jan 5, 2026
SpringHill Suites by Marriott Winchester
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, (2239)
"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 ￥15,469
￥16,831 total
includes taxes & fees
Dec 30 - Dec 31
La Quinta Inn & Suites by Wyndham Winchester
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
19.7 km from Winchester Historic District
9.2 out of 10, Wonderful, (418)
"Historic inn. "
United States
David
The price is ￥11,273
￥13,996 total
includes taxes & fees
Dec 29 - Dec 30
Wayside Inn
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, (802)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is ￥14,506
￥15,783 total
includes taxes & fees
Dec 30 - Dec 31
Fairfield Inn & Suites by Marriott Winchester
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, (1001)
"Good condition "
United States
Phillip
The price is ￥9,707
￥10,805 total
includes taxes & fees
Dec 29 - Dec 30
Super 8 by Wyndham Front Royal
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, (851)
"Super friendly reception and perfectly clean room. "
United States
Dwight
The price is ￥16,562
￥18,765 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Hampton Inn Winchester N/Conference Center, VA
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 ￥23,651
￥30,403 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hillbrook Inn
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, (541)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is ￥9,707
￥10,805 total
includes taxes & fees
Dec 29 - Dec 30
Twi-Lite 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, (1089)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is ￥15,098
￥16,428 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn & Suites Winchester
In-room safe, desk, iron/ironing board, bed sheets
TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
3.2 km from Winchester Historic District
8.8 out of 10, Excellent, (482)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is ￥16,769
￥18,245 total
includes taxes & fees
Dec 30 - Dec 31
TownePlace Suites by Marriott Winchester
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
2.1 km from Winchester Historic District
8.8 out of 10, Excellent, (513)
"Great hotel"
United States
DONNA D
The price is ￥15,793
￥17,894 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Hilton Garden Inn 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
2.9 km from Winchester Historic District
9.0 out of 10, Wonderful, (806)
"Everything was great / thank you!"
United States
Mark
The price is ￥17,379
￥18,909 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Holiday Inn Express Hotel & Suites Winchester by IHG
Front of property - evening/night
Relax Inn Motel

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.7 km from Winchester Historic District
8.2 out of 10, Very Good, (259)
"Clean, and nice rooms, friendly staff"
United States
James
The price is ￥10,647
￥11,849 total
includes taxes & fees
Dec 29 - Dec 30
Relax Inn Motel
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 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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Parking was easy, right off the highway The room was immaculate, nothing dirty at all. Did not have the breakfast "
Shawn 2-night trip
Posted 3 days ago
Quality Inn Winchester

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.
Where can I learn more about changing or cancelling my trip to Winchester Historic District?
For additional details about picking new dates or cancelling your trip to Winchester Historic District, head over to our customer service page.
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.