Winchester

Travel Guide

Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Where to stay in Winchester

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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
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Winchester Historic District

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

Winchester Historic District
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

2 out of 5
991 Millwood Pike, Winchester, VA
The price is HK$536 per night from 2 Nov to 3 Nov
HK$536
HK$583 total
2 Nov - 3 Nov
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
7.4/10 Good! (1,000 reviews)
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.

Reviewed on 22 Oct 2025

Red Roof Inn Winchester, VA
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is HK$797 per night from 9 Nov to 10 Nov
HK$797
HK$867 total
9 Nov - 10 Nov
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,182 reviews)
Good

Reviewed on 25 Oct 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is HK$786 per night from 31 Oct to 1 Nov
HK$786
HK$855 total
31 Oct - 1 Nov
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 breakfast and the helpful ...
9.4/10 Exceptional! (1,038 reviews)
Amazing so clean Greta breakfast

Reviewed on 21 Oct 2025

Comfort Inn & Suites 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.
Hidden Gem in the woods with hot tub

Hidden Gem in the woods with hot tub

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, a pool table, and patios. Popular attractions Berkeley Springs Antique Mall and Ice House are located ...
9.4/10 Exceptional! (82 reviews)
We loved this little cabin! It was so cozy and just 20-30 minutes from anything in town.

Reviewed on 11 Aug 2025

Hidden Gem in the woods with hot tub
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Cacapon Golf Course and Colonial ...
9.8/10 Exceptional! (272 reviews)
Super cozy, quiet, very clean and very comfortable bed! The host was wonderful and responded to all of my questions. We will def. be back!

Reviewed on 17 Oct 2025

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
9.8/10 Exceptional! (48 reviews)
This was a nice property. It was tucked away in the community yet very centrally located to the town and park. Private. If you have issues with mobility and are a bigger individual, this could be a challenge for a comfortable stay. The shower is located on the 2nd floor and is at best 32”x32” in ...

Reviewed on 6 Oct 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
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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