Winchester Travel Guide

Tourist Guide

Winchester
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

Where to stay in Winchester

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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
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Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Winchester Historic District
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 AU$179 per night from 23 Sept to 24 Sept
AU$179
23 Sept - 24 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,152 reviews)
"Easy access to the highway as we passed through."

Reviewed on 13 Sept 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
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 29 Sept to 30 Sept
AU$143
29 Sept - 30 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,342 reviews)
"Close to route 81"

Reviewed on 19 Sept 2025

Microtel 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 AU$158 per night from 28 Sept to 29 Sept
AU$158
28 Sept - 29 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,008 reviews)
Excellent hotel.
"The hotel was very nice and the staff was great! Check-in was easy and very helpful. We had our breakfast included which worked out well. Tina, our server, was above and beyond. She was so friendly and offered my husband a few suggestions which was wonderful. Highly recommend anyone staying ..."

Reviewed on 16 Sept 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,006 properties in Winchester
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.
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Rileyville
Stay at this vacation home in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.8/10 Exceptional! (97 reviews)
"Very nice, clean. Loved the area."

Reviewed on 6 Sept 2025

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Cacapon Golf Course and Colonial ...
9.8/10 Exceptional! (263 reviews)
"We had a great stay. Everything was as described- we wanted a quiet and relaxing trip, which we got. The owners responded in timely manner and gave is any info we needed or requested. We were not bothered at all. The only reason I didn’t give it 5 stars was because the AC dripped and that caused ..."

Reviewed on 27 Aug 2025

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Road Haven 1830

Road Haven 1830

3 out of 5
355 Orchard Drive, Mount Jackson, VA
Stay at this 3-star apartment in Mount Jackson. Enjoy free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.4/10 Exceptional! (36 reviews)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"

Reviewed on 3 June 2025

Road Haven 1830
See all properties in Winchester
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.

Popular places to visit

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
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

Winchester Medical Center

If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

Winchester Medical Center

Shenandoah University

Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah University

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Apple Blossom Mall

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

Cities near Winchester

Photo by KM Moore

Berryville

Other places like Winchester