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 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.
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 Bright Box Theater and Shenandoah Valley Discovery Museum 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 Shenandoah Valley Discovery Museum.

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 ￥13,678 per night from Nov 8 to Nov 9
￥13,678
￥15,223 total
Nov 8 - Nov 9
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 ...
9.2/10 Wonderful! (1,443 reviews)
"As a frequent traveler, everything was excellent"

Reviewed on Oct 12, 2026

Microtel Inn & Suites by Wyndham Winchester
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 ￥20,640 per night from Oct 28 to Oct 29
￥20,640
￥23,385 total
Oct 28 - Oct 29
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,001 reviews)
"The staff was just not welcoming or helpful."

Reviewed on Oct 7, 2026

The George Washington Hotel, A Wyndham Grand Hotel
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is ￥13,501 per night from Nov 1 to Nov 2
￥13,501
￥15,026 total
Nov 1 - Nov 2
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 helpful staff in our reviews. ...
9.2/10 Wonderful! (1,003 reviews)
"Brittany at the front desk was very efficient and friendly at both Checkin and Checkout."

Reviewed on Oct 11, 2026

TRU By Hilton 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 WiFi, free parking, and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.6/10 Exceptional! (52 reviews)
"Depending on the room One of the rooms was upstairs - no elevator or person to assist. Just not too convenient for older travelers."

Reviewed on Oct 6, 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 WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
9.8/10 Exceptional! (73 reviews)
"Rental was clean and check in process was easy"

Reviewed on Sep 18, 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub
Canal Cabins

Canal Cabins

3 out of 5
143 Louie's Ln Paw Paw WV
Stay at this cabin in Paw Paw. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Paw Paw Tunnel and Sideling Hill Wildlife Management ...
9.8/10 Exceptional! (19 reviews)
"After many miles of riding on the GAP and C&O Towpath, the Canal Cabins were a welcome and much needed hiatus! The cabin was cozy and clean, air conditioned, with many personal touches one would need, like bike tools! The bathroom was clean and the shower was hot. And free laundry! Would highly recommend ..."

Reviewed on Oct 7, 2026

Canal Cabins
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 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 mountainous landscape 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

Other places like Winchester

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