Old Town Winchester, VA

Name: Holiday Inn Winchester Se-Historic Gateway by IHG
Price range: $110 total
Rating: 9

Winchester

Visit Old Town Winchester

Things to do

Hotels

Winchester Travel Guide

Popular places to visit

Museum of the Shenandoah Valley

5/5(20 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Jim Barnett Park

4/5(1 review)

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Bright Box Theater

4.5/5(4 reviews)

Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.

Shenandoah Valley Discovery Museum

4.5/5(11 reviews)

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

George Washington's Office

You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants.

Old Town Winchester Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$120 nightly

$136 total

Jun 21 - Jun 22

Total with taxes and 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! (1,001 reviews)

"Clean charming place to stay in the area"

Reviewed on Jun 3, 2026

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

$86 nightly

$98 total

Jun 21 - Jun 22

Total with taxes and 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 ...

9/10 Wonderful! (1,003 reviews)

"Staff was friendly, room was clean, bed comfortable, great value!"

Reviewed on Jun 3, 2026

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

$99 nightly

$109 total

Jul 5 - Jul 6

Total with taxes and 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. ...

9/10 Wonderful! (905 reviews)

"Gentleman at desk was friendly and very helpful. We had asked for an accessible room, and he explained that they had handicapped tubs, not showers. He then offered a regular room with step in shower, explaining that toilets were low, I chose shower walk in. Room was clean and well appointed Shower ..."

Reviewed on Jun 3, 2026

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

$71 nightly

$77 total

Jun 7 - Jun 8

Total with taxes and fees

Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...

8.6/10 Excellent! (1,053 reviews)

"The room was very clean and the staff was friendly."

Reviewed on Jun 2, 2026

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

$91 nightly

$99 total

Jun 14 - Jun 15

Total with taxes and 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 and the clean ...

9.2/10 Wonderful! (1,461 reviews)

"Convenient location for travelers, clean room, comfortable beds, gym and indoor pool looked nice although I did not use them."

Reviewed on Jun 3, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

$101 nightly

$110 total

Jul 5 - Jul 6

Total with taxes and 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 ...

9/10 Wonderful! (1,001 reviews)

"It was very clean and the bes was super comfortable. Did not eat the breakfast so I don't know how it was. Staff was really friendly"

Reviewed on May 30, 2026

See all 367 properties in Old Town 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.