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

Default Image

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
Default Image

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
Fully refundableReserve now, pay when you stay
The price is £87 per night from 15 Sept to 16 Sept
£87
15 Sept - 16 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! (2,138 reviews)
"We mistakenly left a watch in the room after we checked out, and the front-desk person let us go back to check the room about an hour later. Fortunately, the watch was found!"

Reviewed on 9 Sep 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is £55 per night from 14 Sept to 15 Sept
£55
14 Sept - 15 Sept
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! (1,090 reviews)
"Staff is very accommodating and efficient. Room was clean, bed very comfortable. Housekeeper does a fantastic job. Breakfast is very good. Hotel is pet friendly which we appreciate."

Reviewed on 7 Sep 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 £80 per night from 21 Sept to 22 Sept
£80
21 Sept - 22 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! (1,000 reviews)
"Very clean & comfortable. Staff was very helpful & pleasant."

Reviewed on 8 Sep 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 1,996 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, VA
Stay at this holiday home in Rileyville. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.8/10 Exceptional! (97 reviews)
"Very nice, clean. Loved the area."

Reviewed on 6 Sep 2025

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville, VA
Stay at this family-friendly cabin in Rileyville. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Chalybeate Spring and Fort Valley Public ...
9.6/10 Exceptional! (272 reviews)
"This cabin was fantastic! So comfortable and cozy - it was a perfect place to rest and relax after hiking or boating. We will definitely be coming back!"

Reviewed on 21 Aug 2025

Falling Leaf Cabin - Rustic Charm With Modern Decor!
Family Farmhouse Inn

Family Farmhouse Inn

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 Jun 2025

Family Farmhouse Inn
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 Fernando Begay

Front Royal

Berkeley Springs State Park which includes a park

Berkeley Springs

Other places like Winchester