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
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
The price is AU$199 per night from 26 Oct to 27 Oct
AU$199
26 Oct - 27 Oct
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! (1,015 reviews)
"Free Breakfast and parking. Close to many restaurants and shops"

Reviewed on 10 Oct 2025

Hampton Inn Winchester-University/Mall Area
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$172 per night from 2 Nov to 3 Nov
AU$172
2 Nov - 3 Nov
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! (2,171 reviews)
"Great location."

Reviewed on 6 Oct 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 AU$116 per night from 20 Oct to 21 Oct
AU$116
20 Oct - 21 Oct
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,076 reviews)
"Air conditioner works fine comfy bed! I have stayed here several times. Breakfast is not awesome but decent!! Coffee is awesome! :) I will stay here again"

Reviewed on 6 Oct 2025

Travelodge by Wyndham Winchester
See all 2,021 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.
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
10/10 Exceptional! (46 reviews)
Peaceful forest retreat
"We loved our stay at Dreamtime!"

Reviewed on 12 Aug 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
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
Private, light filled retreat space... with your own pickleball court!

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (50 reviews)
"This was our fourth time staying on the property and we loved this house the most! Beautiful views and everything we needed!We can always count on it being very clean, which we appreciate! We love that it is close to the bike trails as well!Berkeley springs had some awesome new restaurants since ..."

Reviewed on 2 Oct 2025

Private, light filled retreat space... with your own pickleball court!
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