Winchester Travel Guide

Tourist Guide

Winchester
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings
A rocky coastline with waves crashing against the shore, a forested cliff, and a clear sky.
Winchester
Winchester

Where to stay in Winchester

Find the best Winchester areas for the activities you enjoy most. Learn more about Winchester
Learn more about Winchester
The Courthouse in Winchester, Virginia.

Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

Photo by Fernando Begay
Open Photo by Fernando Begay

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is ฿3,252 per night from 28 Jun to 29 Jun
฿3,252
฿3,685 total
28 Jun - 29 Jun
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,007 reviews)
"Quick & easy."

Reviewed on 19 Jun 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is ฿2,548 per night from 5 Jul to 6 Jul
฿2,548
฿2,810 total
5 Jul - 6 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (972 reviews)
"Five stars throughout the hotel ,nice place"

Reviewed on 20 Jun 2026

TRU By Hilton Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
The price is ฿2,341 per night from 22 Jun to 23 Jun
฿2,341
฿2,547 total
22 Jun - 23 Jun
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,050 reviews)
"First room smelled like cigarette smoke. They were accommodating about getting us new room."

Reviewed on 20 Jun 2026

Travelodge by Wyndham Winchester
See all 2,088 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.
Roadhaven1830

Roadhaven1830

3 out of 5
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge are located ...
Roadhaven1830
Canal Cabins

Canal Cabins

3 out of 5
143 Louie's Ln Paw Paw WV
Stay at this cabin in Paw Paw. Enjoy free Wi-Fi, free parking and daily housekeeping. Popular attraction Paw Paw Tunnel is located nearby.
9.6/10 Exceptional! (15 reviews)
"Everything was perfect. Loved the quirkiness of this accommodation and the bathrooms were immaculate. Only a minor detour for cyclists on the C&O and the nearby gas station provided enough options for dinner and breakfast."

Reviewed on 9 Jun 2026

Canal Cabins
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

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(1 review)

You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes 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. Visit the top-notch restaurants or cosy cafes in this walkable area.

Jim Barnett Park

Shenandoah University

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

Shenandoah University

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 savour the top-notch restaurants.

Patsy Cline Historic House

Winchester Little Theater

Enjoy a show at Winchester Little Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Winchester Little Theater

Bright Box Theater

Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Bright Box Theater

Cities near Winchester

Berkeley Springs

Berkeley Springs

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