Winchester, VA

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 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.

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 Shenandoah Valley Discovery Museum.

Winchester Historic District
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
$99 nightly
The price is $107 total per night from Dec 28 to Dec 29
$107 total
Dec 28 - Dec 29
Total with taxes and 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 ...
9.2/10 Wonderful! (2,237 reviews)
The breakfast staff is helpful

Reviewed on Dec 22, 2025

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

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
$79 nightly
The price is $86 total per night from Dec 29 to Dec 30
$86 total
Dec 29 - Dec 30
Total with taxes and 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 and the clean ...
9/10 Wonderful! (1,395 reviews)
Yes the room was spotless and the staff have been great

Reviewed on Dec 22, 2025

Microtel Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Jan 14 to Jan 15
$74 total
Jan 14 - Jan 15, 2026
Total with taxes and 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. ...
8.4/10 Very Good! (1,089 reviews)
Everything was fine except your Breakfast pretty much only had instant cereal, apples, orange juice, and toast.

Reviewed on Dec 16, 2025

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.
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 ...
9.8/10 Exceptional! (50 reviews)
I took my Mother here for her 80th Bday getaway. It was so quiet and peaceful and relaxing. We had everything we needed. I was so impressed by the cleanliness and quaint decor of this A-Frame. The beds were wonderfully comfortable. We sat at the table and made dinners, did puzzles and listened to ...

Reviewed on Dec 7, 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...
10/10 Exceptional! (327 reviews)
Appreciated the great communication the host provided. We REALLY appreciated just how clean the cabin was. It was such a nice cabin to stay in for a quick 2-night get-away. It was the perfect layout and size for a cozy place for just the two of us. Hot tub was wonderful (and so clean!!!). The firepit ...

Reviewed on Nov 19, 2025

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Hidden Gem in the woods with hot tub

Hidden Gem in the woods with hot tub

Berkeley Springs WV
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! (87 reviews)
The cabin was very clean, well equipped, and the amenities were plentiful. It was also private and was everything I was expecting based on the property's description. I would rent it again.

Reviewed on Dec 7, 2025

Hidden Gem in the woods with 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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