Winchester Historic District Travel Guide

Winchester

Winchester Historic District
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Popular places to visit

Handley Regional Library

Handley Regional Library

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Handley Regional Library
Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(1 review)

You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley

Shenandoah Valley Discovery Museum

4/5(1 review)

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

Bright Box Theater

Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Bright Box Theater

Winchester Little Theater

Enjoy a show at Winchester Little Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Winchester Little Theater

Stonewall Jackson's Headquarters

Find out about the history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Visit the top-notch restaurants or cosy cafes in this walkable area.

Stonewall Jackson's Headquarters

Top hotels in Winchester Historic District

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
The price is ₹10,805 per night from 10 Jul to 11 Jul
₹10,805
₹12,243 total
10 Jul - 11 Jul
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (1,001 reviews)
"Beautiful old world hotel. Good service, good food and Excellent coffee. Better than any hotel I have stayed at, coffee-wise."

Reviewed on 2 Jul 2025

The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is ₹5,887 per night from 9 Jul to 10 Jul
₹5,887
₹6,406 total
9 Jul - 10 Jul
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,116 reviews)
"Good place for the price, complimentary breakfast was nice"

Reviewed on 3 Jul 2025

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
The price is ₹7,593 per night from 20 Jul to 21 Jul
₹7,593
₹8,518 total
20 Jul - 21 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,001 reviews)
"It’s a lovely property. Clean, updated, and friendly staff."

Reviewed on 30 Jun 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is ₹9,368 per night from 6 Jul to 7 Jul
₹9,368
₹10,192 total
6 Jul - 7 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,067 reviews)
"I’ve had very pleasant experiences at this property. Great staff and great location right off of the highway with restaurants and shopping nearby."

Reviewed on 3 Jul 2025

La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
The price is ₹7,440 per night from 10 Jul to 11 Jul
₹7,440
₹8,094 total
10 Jul - 11 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,286 reviews)
"Loved our stay super comfy beds!"

Reviewed on 29 Jun 2025

Microtel Inn & Suites by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
The price is ₹6,092 per night from 10 Jul to 11 Jul
₹6,092
₹6,780 total
10 Jul - 11 Jul
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8/10 Very Good! (1,003 reviews)
"We have stayed here twice now after finding it so close to Hey81, it’s out half way point between Nc and NY. friendly staff very clean amazing price spacious clean modern bedroom king bed with a very large flat screen tv, even graciously offers some breakfast items a great value this is our new go ..."

Reviewed on 2 Jul 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
See all 367 properties in Winchester Historic District
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.

Other neighbourhoods around Winchester Historic District

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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.

Old Town Winchester

Winchester Historic District Travel Guide