Winchester

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 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 popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

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 Stonewall Jackson's Headquarters.

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 HK$730 per night from 13 Aug to 14 Aug
HK$730
HK$836 total
13 Aug - 14 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,015 reviews)
"no phone cord for the hotel phone so I couldn't call room to room and there were only 3 bath towels for 4 people but both were easy fixes. But my reservation said free breakfast and they wanted $10 for 2 people, so not sure what that was about"

Reviewed on 7 Aug 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
The price is HK$605 per night from 23 Aug to 24 Aug
HK$605
HK$685 total
23 Aug - 24 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,009 reviews)
"The staff went above and beyond to make sure we were comfortable. The hotel was clean and the room was spacious."

Reviewed on 8 Aug 2026

Spark 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 HK$958 per night from 30 Aug to 31 Aug
HK$958
HK$1,086 total
30 Aug - 31 Aug
includes taxes & fees
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 clean rooms ...
9.4/10 Exceptional! (1,015 reviews)
"All amenities were excellent"

Reviewed on 8 Aug 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 2,100 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.
Wild And Wonderful Silos

Wild And Wonderful Silos

Harpers Ferry WV
Stay at this cabin in Harpers Ferry. Enjoy free Wi-Fi, a sauna and patios. Popular attractions Harpers Ferry National Historical Park and Hollywood Casino at ...
8.2/10 Very good! (26 reviews)
"Pros- close to activities, cute home, large outdoor area, supplied coffee & variety of shower soaps. Great water pressure in shower. Fire pit was nice, need to take kindling. Bathrobes provided. Cons- stairs are treacherous. Railing is not attached properly. Weeds are taking over property. Walkway ..."

Reviewed on 11 Jul 2026

Wild And Wonderful Silos
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Edinburg VA
Stay at this holiday home in Woodstock. Enjoy a garden, laundry facilities and patios. Popular attractions Shenandoah Vineyards and Edinburg Mill Museum are ...
10/10 Exceptional! (415 reviews)
"Outstanding Property in Every Possible Way!My husband and I were lucky enough to celebrate our minimoon at Deer Haven and it was exceptional in every way! The pictures don't even do the place justice. The house was spacious, spotless clean, and both decks were incredible. The front deck offered those ..."

Reviewed on 2 Aug 2026

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Roadhaven1830

Roadhaven1830

3 out of 5
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.6/10 Exceptional! (46 reviews)
"Everything was well decorated and clean. The place was quiet except that it is right by Rt. 81. The property is maintained well but if you want to enjoy their lovely and spacious yard bring mosquito repellent as I was bitten several times. My husband in the other hand had a great time on the swing ..."

Reviewed on 1 Aug 2026

Roadhaven1830
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 browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.
See properties
A lake surrounded by forested hills and a small town.

Gore

Other places like Winchester

Explore a world of travel with Expedia