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.
The Historic Handley Regional Library Building, Winchester, Virginia, USA
A rocky coastline with waves crashing against the shore, a forested cliff, and a clear sky.
A serene garden with a clear stream, lush greenery, and flowering plants.

Where to stay in Winchester

Find the best Winchester areas and neighborhoods 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 known for its ample dining options, and you can make a stop by Shenandoah Valley Discovery Museum and Bright Box Theater while in the area.

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 Winchester Little Theater.

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
The price is ￥15,777 per night from Sep 27 to Sep 28
￥15,777
￥18,038 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Holiday Inn Winchester Se-Historic Gateway by IHG
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is ￥19,471 per night from Sep 7 to Sep 8
￥19,471
￥22,061 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is ￥10,990 per night from Sep 1 to Sep 2
￥10,990
￥12,122 total
Sep 1 - Sep 2
includes taxes & 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. ...
8.6/10 Excellent! (1,085 reviews)
"The room was spacious and clean. Parking easy. Staff was pleasant and accommodating."

Reviewed on Aug 28, 2026

Travelodge by Wyndham Winchester
See all 2,096 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 WiFi, free parking, and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.6/10 Exceptional! (49 reviews)
"5 night stay. Comphy bed and well stocked with pillows, towels and essentials. Quiet lovely surrounding grounds. Easy check in and departure. Close to route 11 for the yard crawl and things to do!"

Reviewed on Aug 17, 2026

Roadhaven1830
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley Public Library are located ...
9.8/10 Exceptional! (333 reviews)
"The property was clean and homie. We immediately felt relaxed as soon as we walked in. We had plenty to do in the house, even with the bit of rain we had - our kids had their pick at board games . Would definitely recommend and book again!"

Reviewed on Aug 9, 2026

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Silo Tiny House Cabin

Silo Tiny House Cabin

Harpers Ferry WV
Stay at this cabin in Harpers Ferry. Enjoy free WiFi, a sauna, and patios. Popular attractions Harpers Ferry National Historical Park and Hollywood Casino at ...
8.2/10 Very Good! (30 reviews)
"Great stay! Very comfortable bed. The sauna is a wonderful touch."

Reviewed on Aug 11, 2026

Silo Tiny House Cabin
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

Museum of the Shenandoah Valley

8.8/10 (129 reviews)
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
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Cities near Winchester

A mountain range with autumn foliage.

Front Royal

An aerial view of a railway station with multiple tracks, a steam locomotive emitting smoke, and a blue train car.

Strasburg

A park with a bench, trees, and a building with colorful facades.

Berkeley Springs

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