Winchester, VA

Travel 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 known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

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 Shenandoah Valley Discovery Museum.

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 SAR 389 per night from Jul 6 to Jul 7
SAR 389
SAR 423 total
includes taxes & fees
6 Jul - 7 Jul
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 ...
9/10 Wonderful! (2,042 reviews)
"Nice hotel. Nice staff. Thin walls, noisy area."

Reviewed on 31 May 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
Fully refundable
The price is SAR 349 per night from Jun 15 to Jun 16
SAR 349
SAR 391 total
includes taxes & fees
15 Jun - 16 Jun
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! (1,000 reviews)
"This is a very nice Holiday Inn and for a reasonable price. The bed was comfortable and the frig was larger, but it did not have a freezer for our icee. Nice large walk in shower and the breakfast was superb! Great food and service even though i got there 20 minutes before closing they acted like, ..."

Reviewed on 2 June 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is SAR 259 per night from Jul 3 to Jul 4
SAR 259
SAR 282 total
includes taxes & fees
3 Jul - 4 Jul
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. ...
8.2/10 Very Good! (1,111 reviews)
"Right off the exit near Restaurants. Plenty of parking, room was spacious and clean and check in was a breeze"

Reviewed on 4 June 2025

Travelodge by Wyndham Winchester
See all 1,970 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.
Star view cabin-Riverfront
Star view cabin-Riverfront
Rileyville
Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
9.6/10 Exceptional! (284 reviews)
Mountains and River
"Good space to relax in the mountains."

Reviewed on 1 June 2025

Star view cabin-Riverfront
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! (32 reviews)
Fantastic
"Everything about this day was great. Everything was explained as far as remotes and use of technology. It was comfy, cozy and beautiful."

Reviewed on 1 June 2025

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

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Museum of the Shenandoah Valley
Staircase at Handley Library

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Handley Regional Library

Shenandoah University

4.5/5(69 reviews)

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

Shenandoah University

Winchester Medical Center

4/5(39 reviews)

Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

Winchester Medical Center

Apple Blossom Mall

4/5(105 reviews)

You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Apple Blossom Mall

Rock Harbor Golf Course

3.5/5(3 reviews)

Enjoy a round of golf in Winchester at Rock Harbor Golf Course. While in this walkable area, you can savor the top-notch restaurants.

Rock Harbor Golf Course

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