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.
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 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 Shenandoah Valley Discovery Museum.

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 28 Sept to 29 Sept
HK$605
HK$685 total
28 Sept - 29 Sept
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! (1,002 reviews)
"This hotel is very satisfactory other than the soft water. Please add less water softener!"

Reviewed on 9 Sept 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$1,022 per night from 28 Sept to 29 Sept
HK$1,022
HK$1,158 total
28 Sept - 29 Sept
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! (1,005 reviews)
"The property and room were beautiful. We enjoyed our stay. Parking is limited but understandable for the location of the hotel."

Reviewed on 10 Sept 2026

The George Washington Hotel, A Wyndham Grand Hotel
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$808 per night from 11 Oct to 12 Oct
HK$808
HK$923 total
11 Oct - 12 Oct
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 ...
Holiday Inn Winchester Se-Historic Gateway by IHG
See all 2,147 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 Wi-Fi, free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.6/10 Exceptional! (50 reviews)
"Cute backyard with multiple games. Room was very clean and comfortable and the bed was super soft. Overall I would definitely come back here."

Reviewed on 6 Sept 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 Wi-Fi, laundry facilities and patios. Popular attractions Chalybeate Spring and Fort Valley Public Library are located ...
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
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 Wi-Fi, laundry facilities and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
9.8/10 Exceptional! (69 reviews)
"We enjoyed the layout of the house! Everything felt cozy. My wife wanted to make it known that she did not find the mattress on the main floor to be very comfortable, but she is a little spoiled with hers at home. Otherwise very well kept and organized house that was perfectly nestled in behind Berkeley ..."

Reviewed on 23 Aug 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub
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

Things to do

Shenandoah National Park Self-Driving Audio Tour

Shenandoah Tour: Self-Guided Drive

HK$133
per traveller
98% of travellers recommend
Shenandoah Tour: Self-Guided Drive
See all activities in Winchester
A lake surrounded by forested hills and a small town.

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