Winchester

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
The price is CA $132 per night from Jul 1 to Jul 2
CA $132
CA $150 total
Jul 1 - Jul 2
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! (1,008 reviews)
"Staff was friendly and responsive. Room was clean. We did not use amenities, but they seemed nice enough"

Reviewed on Jun 21, 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 CA $111 per night from Jul 1 to Jul 2
CA $111
CA $122 total
Jul 1 - Jul 2
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! (976 reviews)
"An “Excellent” rating is True for “TRU”. Plenty of parking space, lively staff, vibrant interiors and decor, work space and game options, adequate luggage karts, clean rooms, and hot breakfast. Everything that needs to be in place was in place for a comfortable and peaceful stay."

Reviewed on Jun 21, 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 CA $98 per night from Jul 1 to Jul 2
CA $98
CA $108 total
Jul 1 - Jul 2
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! (1,051 reviews)
"First room smelled like cigarette smoke. They were accommodating about getting us new room."

Reviewed on Jun 20, 2026

Travelodge by Wyndham Winchester
See all 2,094 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 May 28, 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

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 top-notch restaurants or charming coffeehouses 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

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

Winchester Little Theater

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

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

Cities near Winchester

White Post

White Post

Other places like Winchester