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 rocky coastline with waves crashing against the shore, a forested cliff, and a clear sky.
Weeping willow branches reaching towards river waters, different flowers growing on the shores. Winchester city park.
A building with a green roof and ornate architectural details.

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 Winchester Little Theater and Shenandoah Valley Discovery Museum.

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 ￥13,489 per night from Aug 2 to Aug 3
￥13,489
￥15,500 total
Aug 2 - Aug 3
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
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is ￥14,791 per night from Jul 26 to Jul 27
￥14,791
￥16,462 total
Jul 26 - Jul 27
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. ...
TRU By Hilton 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 ￥21,174 per night from Aug 17 to Aug 18
￥21,174
￥23,991 total
Aug 17 - Aug 18
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 ...
9.4/10 Exceptional! (1,003 reviews)
"I loved the pool. The bed was really comfy and the water pressure was excellent. However, I didn't like the parking situation."

Reviewed on Jul 18, 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 2,108 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 parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge are located ...
9.6/10 Exceptional! (44 reviews)
"Quiet, recently renovated and very cute suite with thoughtful accommodations. The owner was very nice and pleasant 😊We stayed in the Elizabeth suite and would definitely stay again!"

Reviewed on Jul 15, 2026

Roadhaven1830
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! (24 reviews)
"Pictures on internet were very nice and clean. Upon arriving was a different case property had junk behind the silo walkway was not stable uneven round rocks to walk on especially for the distance from the parking.. upon entering the silo not clean shower contained mold, and mildew dead flies on ..."

Reviewed on Jun 15, 2026

Silo Tiny House Cabin
Private, light filled retreat space... with your own pickleball court!

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (92 reviews)
"The photos are lovely, but the experience of being there is so much more. We loved it! It was so peaceful and lovely. We watched deer families every night and saw a fox as well. So wonderful to see them enjoy the woods with no fear. There was easy access to town and Cacapon. The area has plenty of ..."

Reviewed on Jul 17, 2026

Private, light filled retreat space... with your own pickleball court!
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.
See properties

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

Other places like Winchester

Explore a world of travel with Expedia