Winchester, VA

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 and neighborhoods for the activities you enjoy most.

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.

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 AED 257 per night from Dec 1 to Dec 2
AED 257
AED 284 total
1 Dec - 2 Dec
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 AED 303 per night from Nov 8 to Nov 9
AED 303
AED 337 total
8 Nov - 9 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
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 AED 380 per night from Nov 8 to Nov 9
AED 380
AED 423 total
8 Nov - 9 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 ...
9.2/10 Wonderful! (2,272 reviews)
"Arrived late. Staff member at desk very friendly and welcoming. Morning staff very friendly. Room spacious liked the floor plan"

Reviewed on 3 November 2026

La Quinta Inn & Suites 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.
Roadhaven1830

Roadhaven1830

3 out of 5
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free WiFi, free parking, and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
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 WiFi, 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 October 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 WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...
10/10 Exceptional! (390 reviews)
"Second visit to this property and we like it alot. The basics are there but definitely bring other cookware if you are the type of person to cook at home rather then eat out all the time. Overall pleased and have recommended to other friends and family of ours."

Reviewed on 1 November 2026

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

Other places like Winchester