Winchester, VA

Travel Guide

Winchester
Winchester
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings
Handley Library
Gardens at Glen Burnie House.

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Where to stay in Winchester

The Courthouse in Winchester, Virginia.

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
Buildings and streets in the historic part of the ancient city of Winchester in Virginia.

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 AED 401 per night from Mar 5 to Mar 6
AED 401
AED 437 total
5 Mar - 6 Mar
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 breakfast and the helpful ...
9.2/10 Wonderful! (2,281 reviews)
Clean room. Comfortable bed. Easy in and out. Reasonably close to Old Town Winchester in historic district. Friendly staff.

Reviewed on 1 March 2026

La Quinta Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is AED 449 per night from Mar 9 to Mar 10
AED 449
AED 508 total
9 Mar - 10 Mar
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,006 reviews)
Room was clean but a lil noisy. We didn't have the best room location. Must have been close to a staff area

Reviewed on 2 March 2026

The George Washington Hotel, A Wyndham Grand Hotel
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 323 per night from Mar 12 to Mar 13
AED 323
AED 363 total
12 Mar - 13 Mar
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,004 reviews)
Great room and service

Reviewed on 2 March 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,052 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.
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Cacapon Golf Course and Colonial ...
9.8/10 Exceptional! (304 reviews)
The only complant is the toilet paper everything else great

Reviewed on 15 February 2026

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Star view cabin-Riverfront

Star view cabin-Riverfront

Rileyville VA
Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
Star view cabin-Riverfront
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ...
9.8/10 Exceptional! (308 reviews)
The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly.

Reviewed on 18 February 2026

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

Museum of the Shenandoah Valley
Jim Barnett park

Jim Barnett Park

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Jim Barnett Park

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

ValleyHealth Winchester Medical Center

Though ValleyHealth 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.

ValleyHealth Winchester Medical Center

Patsy Cline Historic House

You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savor the top-notch restaurants.

Patsy Cline Historic House

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