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

Default Image

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
Default Image

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
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is AED 383 per night from May 26 to May 27
AED 383
AED 417 total
includes taxes & fees
26 May - 27 May
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,026 reviews)
"It is so clean and quiet. The free breakfasrt was great and has many options. I would highly recommend"

Reviewed on 19 May 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
Fully refundableReserve now, pay when you stay
The price is AED 239 per night from May 28 to May 29
AED 239
AED 260 total
includes taxes & fees
28 May - 29 May
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! (1,117 reviews)
"Great place. Easy access. Nice rooms"

Reviewed on 20 May 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 AED 356 per night from May 25 to May 26
AED 356
AED 399 total
includes taxes & fees
25 May - 26 May
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! (1,001 reviews)
"excellent service"

Reviewed on 20 May 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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 tennis courts, patios, and an in-room coffeemaker. Our guests praise the property condition in our reviews. Popular attractions ...
9.6/10 Exceptional! (283 reviews)
Review
"My family loves Shenandoah NP and we’ve stayed at multiple places. This cabin was perfect for us! The views were amazing!"

Reviewed on 15 May 2025

Star view cabin-Riverfront
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 ...
"Charming cottage was extremely clean with very comfortable bed and couch. Fridge came in handy, and it was easy to view different tv apps/programs. We loved the property and felt like kids playing the games in the yard…what a great set-up with a fire pit and plenty of nice seating! Julie was great ..."

Reviewed on 4 May 2025

Family Farmhouse Inn
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, patios, and an in-room coffeemaker. Popular attractions Frog Valley Artisans, LTD and Colonial Springs ...
9.8/10 Exceptional! (37 reviews)
Dreamtime Cabin
"Lovely cabin, very clean and well maintained. A girlfriend weekend and we wanted a great place to hang out and this fit the bill. We never got the TV to work but could be user error."

Reviewed on 26 March 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
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

Other places like Winchester