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

Our guide on where to stay in Winchester

Find the best Winchester areas for the activities you enjoy most.

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.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is AU$173 per night from 22 June to 23 June
AU$173
22 June - 23 June
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. ...
9/10 Wonderful! (902 reviews)
"Amazing hotel, allowed me to check in early. Very nice and clean rooms"

Reviewed on 3 June 2026

TRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is AU$147 per night from 1 July to 2 July
AU$147
1 July - 2 July
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! (1,001 reviews)
"Staff was very nice"

Reviewed on 2 June 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 AU$108 per night from 7 June to 8 June
AU$108
7 June - 8 June
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! (1,053 reviews)
"The room was very clean and the staff was friendly."

Reviewed on 2 June 2026

Travelodge by Wyndham 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, light filled retreat space...
     with your own pickleball court!

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy cable/satellite TV service, an in-room coffee maker and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (84 reviews)
"We loved our stay! Very private and clean. We even tried pickleball for the first time. Would highly recommend!"

Reviewed on 31 May 2026

Private, light filled retreat space... with your own pickleball court!
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 Wi-Fi, laundry facilities and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
10/10 Exceptional! (63 reviews)
"Great cabin! Hot tub was nice, house was very clean"

Reviewed on 14 May 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub
Roadhaven1830

Roadhaven1830

3 out of 5
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free parking, a garden and premium bedding. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered ...
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
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.

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