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 top-notch restaurants or cosy cafes in this walkable area.

Handley Regional Library
Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

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

Museum of the Shenandoah Valley

Shenandoah Valley Discovery Museum

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 cosy cafes or top-notch restaurants 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 ฿3,829 per night from 31 Aug to 1 Sept
฿3,829
฿4,338 total
31 Aug - 1 Sept
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! (1,008 reviews)
Super Getaway
"Great old hotel. Quiet, comfortable, beautiful. Staff were wonderful. Perfect location for walking around the downtown mall."

Reviewed on 23 Aug 2025

The George Washington Hotel, A Wyndham Grand Hotel
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 ฿3,325 per night from 1 Sept to 2 Sept
฿3,325
฿3,618 total
1 Sept - 2 Sept
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 ...
9.2/10 Wonderful! (2,129 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on 19 Aug 2025

La Quinta Inn & Suites 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 ฿2,657 per night from 7 Sept to 8 Sept
฿2,657
฿2,989 total
7 Sept - 8 Sept
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! (1,005 reviews)
"Clean and staff was great."

Reviewed on 23 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is ฿2,567 per night from 15 Sept to 16 Sept
฿2,567
฿2,793 total
15 Sept - 16 Sept
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! (1,319 reviews)
"easy to get to, close to where I needed to be."

Reviewed on 19 Aug 2025

Microtel Inn & Suites by Wyndham Winchester
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET, Winchester, VA
The price is ฿3,763 per night from 1 Sept to 2 Sept
฿3,763
฿4,094 total
1 Sept - 2 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (696 reviews)
"Clean and great room layout. Personable staff"

Reviewed on 21 Aug 2025

SpringHill Suites by Marriott 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 ฿2,314 per night from 1 Sept to 2 Sept
฿2,314
฿2,575 total
1 Sept - 2 Sept
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 ...
8.2/10 Very Good! (1,004 reviews)
A night in Virginia
"Room was comfortable. The breakfast was decent. The Mexican restaurant attached is AMAZING. No conditioner and body wash was super low. I’m sure I could have gotten more if I asked but it was not a big deal. I did ask for more towels and they were quickly accommodating."

Reviewed on 19 Aug 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
See all 370 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