Winchester, VA

Travel Guide
Photo by Fernando Begay
Photo by Fernando Begay

Where to stay in Winchester

Holiday shopping in Winchester.

Old Town Winchester

Old Town Winchester is known for its ample dining options, and you can make a stop by Shenandoah Valley Discovery Museum and Apple Blossom Mall while in the area.

Old Town Winchester
See our Where To Stay guide
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA, 22602
The price is $60 per night from Jun 6 to Jun 7
$60
per night
Jun 6 - Jun 7
Stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms ...
7.6/10 Good! (1,001 reviews)
"The hotel was inexpensive, but not cheap. The condition of the room was questionable at first, chipped paint, bathroom access was a little tight at the doorway. But it was comfortable, good power access (we both have CPAPs and it's often difficult for both of us), good shower. We left something important ..."

Reviewed on May 29, 2023

Travelodge by Wyndham Winchester
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, 22602
The price is $117 per night from May 31 to Jun 1
$117
per night
May 31 - Jun 1
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 rooms ...
8.6/10 Excellent! (1,006 reviews)
LaQuinta
"Very clean and bed was comfortable. Wonderful shower. Frig and coffee maker. Very quiet. Will definitely stay here again."

Reviewed on May 28, 2023

La Quinta Inn & Suites by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA, 22602
The price is $106 per night from Jun 13 to Jun 14
$106
per night
Jun 13 - Jun 14
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 ...
8.6/10 Excellent! (1,006 reviews)
"Not so happy about payment had a gift card which they would not take. Just had Ben to another country inn and suites in Roanoke Va. They accepted the gift card but put a hold on my Credit card. We called country in & suites and they said they would get back to us but never did. Not a good look for ..."

Reviewed on May 28, 2023

Country Inn & Suites by Radisson, Winchester, VA
See all 1,620 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.
❤️ Secluded 1940s Romantic Tiny House on the River
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown, WV
Stay at this cabin in Shepherdstown. Enjoy free WiFi, onsite parking, and a porch. Our guests praise the comfy beds and the overall value in our reviews. Popular ...
9.6/10 Exceptional! (26 reviews)
Heaven!
"Imagine… perfect!"

Reviewed on May 24, 2023

❤️ Secluded 1940s Romantic Tiny House on the River
Dreamtime - Modern A-frame Cabin w/ Hot tub
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs, WV
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, onsite parking, and barbecue grills. Popular attractions Frog Valley Artisans, LTD and Colonial Springs ...
10/10 Exceptional! (20 reviews)
Beautiful Cabin in the woods!
"We enjoyed our stay so much! The cabin is beautiful and situated in a great neighborhood with trails pretty much right outside the door! Easy drive to the brewery, winery and to downtown for restaurants and site seeing!"

Reviewed on May 20, 2023

Dreamtime - Modern A-frame Cabin w/ Hot tub
Falling Leaf Cabin Secluded With Mountain View!
Falling Leaf Cabin Secluded With Mountain View!
Rileyville, VA
Stay at this family-friendly cabin in Rileyville. Enjoy WiFi, a patio, and a Smart TV. Our guests praise the comfy rooms in our reviews. Popular attraction Elkwallow ...
9.6/10 Exceptional! (211 reviews)
Beautiful cabin
"This was exactly what my wife and I needed to relax and unwind. Cabin looks small on the outside but looks are deceiving. The layout and design was perfect and allows each space to feel open and comfortable. Only thing I’d say is the view has potential to be awe inspiring if some of the overgrowth ..."

Reviewed on May 19, 2023

Falling Leaf Cabin Secluded With Mountain View!
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

Image for Museum of the Shenandoah Valley

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 charming coffeehouses or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Image for Handley Regional 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 top-notch restaurants or charming coffeehouses in this walkable area.

Handley Regional Library
Image for Shenandoah University

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
Image for Winchester Medical Center

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
Image for Rock Harbor Golf Course

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
Image for Apple Blossom Mall

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

Things to do

Image for 20+ National Parks Self-Guided Driving Tours Bundle

20+ National Parks Self-Guided Driving Tours Bundle

$58
Per adult
100% of travellers recommend
20+ National Parks Self-Guided Driving Tours Bundle
Image for Virginia Winery Day Tour by Spirited Tours

Virginia Winery Day Tour by Spirited Tours

$185
Per adult
Virginia Winery Day Tour by Spirited Tours
Image for NOVA Private Custom Wine Tours & Tasting from DMV

NOVA Private Custom Wine Tours & Tasting from DMV

$799
Per adult
80% of travellers recommend
NOVA Private Custom Wine Tours & Tasting from DMV
See all activities in Winchester

Cities near Winchester

Photo by Michael Gibson

Front Royal

Photo by Stephanie Sutton

Middletown

Photo by Stephanie Sutton

Stephens City

Berkeley Springs State Park which includes a park

Berkeley Springs

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