Winchester, VA

Travel 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 and neighborhoods for the activities you enjoy most.
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.

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
Fully refundableReserve now, pay when you stay
The price is AED 322 per night from Jul 6 to Jul 7
AED 322
AED 365 total
6 Jul - 7 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,007 reviews)
"Quick & easy."

Reviewed on 19 June 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 AED 284 per night from Jul 5 to Jul 6
AED 284
AED 313 total
5 Jul - 6 Jul
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 helpful staff in our reviews. ...
9.2/10 Wonderful! (972 reviews)
"Five stars throughout the hotel ,nice place"

Reviewed on 20 June 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 AED 261 per night from Jun 22 to Jun 23
AED 261
AED 284 total
22 Jun - 23 Jun
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our 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 June 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
Silo Tiny House Cabin

Silo Tiny House Cabin

Harpers Ferry WV
Stay at this cabin in Harpers Ferry. Enjoy free WiFi, a sauna, and patios. Popular attractions Harpers Ferry National Historical Park and Hollywood Casino at ...
8.4/10 Very Good! (23 reviews)
"This place was nice but more like glamping. The property really looked a bit worn. Just an fyi. When it rains you hear every raindrop. The shower is a little weird set up. Stairway to the bedroom was a bit weary. A sliding gate or rail for the upstairs so no one would tumble down the stairs. We stayed ..."

Reviewed on 28 May 2026

Silo Tiny House Cabin
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, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
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

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(20 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
Jim Barnett Park

Jim Barnett Park

4/5(1 review)

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

Jim Barnett Park

Shenandoah University

4.5/5(70 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

Patsy Cline Historic House

4/5(19 reviews)

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

Winchester Little Theater

5/5(3 reviews)

Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.

Winchester Little Theater

Bright Box Theater

4.5/5(4 reviews)

Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.

Bright Box Theater

Other places like Winchester