Winchester Travel Guide

Tourist Guide

Winchester
MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings
Handley Library
Gardens at Glen Burnie House.
A nice 3 block outdoor downtown shopping area with dining and bars also.

Where to stay in Winchester

The Courthouse in Winchester, Virginia.

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.

Old Town Winchester
Buildings and streets in the historic part of the ancient city of Winchester in Virginia.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District
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 ฿3,020 per night from 29 Mar to 30 Mar
฿3,020
฿3,383 total
29 Mar - 30 Mar
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! (1,003 reviews)
Yes

Reviewed on 18 Mar 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,477 per night from 24 Mar to 25 Mar
฿3,477
฿3,784 total
24 Mar - 25 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,272 reviews)
Nice room, friendly staff

Reviewed on 17 Mar 2026

La Quinta Inn & Suites by Wyndham Winchester
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
The price is ฿2,594 per night from 12 Apr to 13 Apr
฿2,594
฿2,823 total
12 Apr - 13 Apr
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,000 reviews)
Yes the kitchen was a blessing

Reviewed on 16 Mar 2026

Sleep Inn & Suites Winchester near University
See all 2,040 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.
Marriott's Manor Club at Ford's Colony

Marriott's Manor Club at Ford's Colony

3.5 out of 5
101 Saint Andrews Dr Williamsburg VA
Stay at this golf condo in Williamsburg. Enjoy free Wi-Fi, 2 outdoor pools and 2 hot tubs. Our guests praise the helpful staff and the property condition in ...
9.2/10 Wonderful! (1,034 reviews)
Clean room.

Reviewed on 17 Mar 2026

Marriott's Manor Club at Ford's Colony
Placemakr Marymount Ballston

Placemakr Marymount Ballston

4 out of 5
1008 N Glebe Rd Arlington VA
Stay at this aparthotel in Arlington. Enjoy free Wi-Fi, a rooftop terrace and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (761 reviews)
Great Stay !!

Reviewed on 16 Mar 2026

Placemakr Marymount Ballston
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
424 Atlantic Avenue Virginia Beach VA
Stay at this aparthotel in Virginia Beach. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff and the clean rooms in their ...
7.8/10 Good! (1,474 reviews)
Very easy check in, pool was nice and convenient for kids, great location to beach

Reviewed on 16 Mar 2026

The Ocean Key Virginia Beach Resort
See all 19,134 properties in Virginia
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.

Popular places to visit

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

5/5(1 review)

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.

Museum of the Shenandoah Valley
Jim Barnett park

Jim Barnett Park

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Jim Barnett Park

ValleyHealth Winchester Medical Center

If ValleyHealth Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

ValleyHealth Winchester Medical Center

Shenandoah University

Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah University

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Apple Blossom Mall

Patsy Cline Historic House

You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savour the top-notch restaurants.

Patsy Cline Historic House

Cities near Winchester

Berkeley Springs State Park which includes a park

Berkeley Springs

Other places like Winchester