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.

Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
$79 nightly
The price is $89 total per night from Sep 14 to Sep 15
$89 total
Sep 14 - Sep 15
Total with taxes and 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 ...
Spark by Hilton Winchester
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
$96 nightly
The price is $107 total per night from Aug 30 to Aug 31
$107 total
Aug 30 - Aug 31
Total with taxes and 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 ...
9/10 Wonderful! (1,025 reviews)
"Very clean property. Extremely helpful staff. Clean rooms. Great value."

Reviewed on Aug 24, 2026

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
$120 nightly
The price is $136 total per night from Sep 7 to Sep 8
$136 total
Sep 7 - Sep 8
Total with taxes and 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
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.
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 ...
Silo Tiny House Cabin
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
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

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Middletown

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

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