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 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 SAR 406 per night from Sep 17 to Sep 18
SAR 406
SAR 442 total
17 Sep - 18 Sep
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! (2,138 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 September 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 SAR 259 per night from Sep 16 to Sep 17
SAR 259
SAR 282 total
16 Sep - 17 Sep
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! (1,090 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 September 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 SAR 364 per night from Sep 21 to Sep 22
SAR 364
SAR 407 total
21 Sep - 22 Sep
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! (1,000 reviews)
"Very clean & comfortable. Staff was very helpful & pleasant."

Reviewed on 8 September 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,002 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 September 2025

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

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville
Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ...
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 August 2025

Falling Leaf Cabin - Rustic Charm With Modern Decor!
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

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

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

Handley Regional Library

Winchester Medical Center

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

Shenandoah University

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

Apple Blossom Mall

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

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 savor the top-notch restaurants.

Shenandoah Valley Discovery Museum

Other places like Winchester