Winchester

Travel Guide

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.
A historic downtown area with a prominent clock tower and a green-roofed building.
A white neoclassical building with columns, an American flag, and a clock tower.
A historic building with a green dome and classical architecture.
A rocky coastline with waves crashing against the shore, a forested cliff, and a clear sky.

Where to stay in Winchester

Find the best Winchester areas for the activities you enjoy most. Learn more about Winchester
Learn more about Winchester
A white neoclassical building with columns, an American flag, and a clock tower.

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.

A red brick church with a blue door and a clock tower.
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 Shenandoah Valley Discovery Museum.

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
The price is HK$557 per night from 27 Oct to 28 Oct
HK$557
HK$614 total
27 Oct - 28 Oct
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Travelodge 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
The price is HK$659 per night from 8 Nov to 9 Nov
HK$659
HK$733 total
8 Nov - 9 Nov
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 ...
9.2/10 Wonderful! (1,440 reviews)
"They had a very nice breakfast. The room was spacious and had a full kitchen."

Reviewed on 26 Oct 2026

Microtel Inn & Suites by Wyndham Winchester
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$840 per night from 28 Oct to 29 Oct
HK$840
HK$935 total
28 Oct - 29 Oct
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,274 reviews)
"The hotel is clean and nice , Also, bed is clean and comfortable. Everything is fit my expectations."

Reviewed on 25 Oct 2026

La Quinta Inn & Suites by Wyndham Winchester
See all 2,231 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 Wi-Fi, free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.4/10 Exceptional! (53 reviews)
"Guests should be aware that you will hear noise from a nearby freeway. If you are relying on the listed twin trundle, be advised that is is more of a small cot with a pad. Would be good for smaller children. The heat in our room was provided by a small space heater. I would ask management to preheat ..."

Reviewed on 24 Oct 2026

Roadhaven1830
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 ...
9.8/10 Exceptional! (77 reviews)
"Had an absolute great time at the property. Host answered all questions and was very personable. The actual property was beautiful and we made good use of the hot tub and wood stove. Plans to come back were made before we even checked out."

Reviewed on 12 Oct 2026

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 Wi-Fi, a garden and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...
10/10 Exceptional! (388 reviews)
"Very nice and clean. Everything you might need in a secluded cabin. The hot tub was perfect! Saw deer each day we were there. Fire ring was nice to have as well."

Reviewed on 16 Oct 2026

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

Stay near popular Winchester attractions

A brick pathway leading to a central lawn area, surrounded by trimmed hedges and trees.
Photo by Tina McClelland
Open Photo by Tina McClelland

Museum of the Shenandoah Valley

8.8/10 (129 reviews)
You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.
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A lake surrounded by forested hills and a small town.

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