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
Sunset evening at Shore Acres Winchester Oregon Coast
Winchester
Winchester

Where to stay in 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.

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
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is ฿2,692 per night from 31 May to 1 Jun
฿2,692
฿3,050 total
31 May - 1 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! (1,021 reviews)
We got in late, and the person at the front desk was a DREAM, even getting us a rollaway bed and making sure we had everything we needed. We will definitely stay there again!

Reviewed on 5 May 2026

Spark 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 ฿2,306 per night from 7 May to 8 May
฿2,306
฿2,509 total
7 May - 8 May
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! (1,056 reviews)
Great check in; bed comfortable; could improve plug ins for cell phones and update lights. Sofa/furniture could becould be updated.

Reviewed on 3 May 2026

Travelodge 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 ฿4,269 per night from 31 May to 1 Jun
฿4,269
฿4,836 total
31 May - 1 Jun
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,004 reviews)
Staff was excellent- friendly, courteous. Helpful. Gym - small - but clean and most that you need. Pool - beautiful- on smaller side. Great bar vibe. Excellent location. This Wyndham so much better quality than the Wyndham we stayed at in Savannah, GA. Uno Pizzaria - connected to hotel - terrible ...

Reviewed on 2 May 2026

The George Washington Hotel, A Wyndham Grand Hotel
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 ...
9.6/10 Exceptional! (40 reviews)
Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back

Reviewed on 12 Apr 2026

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! (14 reviews)
Was an amazing stay. Plan on booking again in future with the kids!

Reviewed on 5 Apr 2026

Canal Cabins
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

Things to do

Cities near Winchester