COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Photo by Fernando Begay

Search Hotels in Old Town Winchester, Winchester

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and holiday rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Top Trending Hotels Near Old Town Winchester, Winchester

Day Inn by Wyndham Charles Town
2 out of 5
642 E Washington Street, Charles Town, WV
Free cancellationReserve now, pay when you stay
The price is £64 per night from 19 May to 19 May
Day Inn by Wyndham Charles Town
Travelodge by Wyndham Winchester
2 out of 5
160 Front Royal Pike, Winchester, VA
Free cancellationReserve now, pay when you stay
The price is £44 per night from 23 May to 23 May
3.6/5Good! (964 reviews)
"When I review a hotel stay, I always take into consideration the price, as everyone should. I tend to stay in an economical place when my need is mainly a bed and a continental breakfast for an overnight stay while traveling. My stay was great. The bed and pillows were very comfortable and the limited ..."

Reviewed on 5 May 2021

Travelodge by Wyndham Winchester
Hillbrook Inn
4 out of 5
4490 Summit Point Road, Charles Town, WV
The price is £110 per night from 1 Jun to 1 Jun
4.8/5Exceptional! (75 reviews)
"Would be perfect in warmer weather. The areal star was the cuisine. Beautiful presentation fine service along with excellent food. Well worth another visit."

Reviewed on 6 Mar 2021

Hillbrook Inn
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
The Carriage Inn B&B
3.5 out of 5
417 E Washington Street, Charles Town, WV
The price is £104 per night from 24 May to 24 May
4.9/5Exceptional! (162 reviews)
"Great location and great hosts. Their B&B has an interesting and important history, adding to the experience of a wonderful stay."

Reviewed on 26 Apr 2021

The Carriage Inn B&B
Red Roof Inn Winchester, VA
2 out of 5
991 Millwood Pike, Winchester, VA
Free cancellationReserve now, pay when you stay
The price is £50 per night from 19 May to 19 May
3.5/5Good! (988 reviews)
"The room was great , very clean just the beds were uncomfortable other than everything was as promised , love using Red Roof Inn in my travels"

Reviewed on 16 May 2021

Red Roof Inn Winchester, VA
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free cancellationReserve now, pay when you stay
The price is £82 per night from 19 May to 19 May
4.4/5Excellent! (995 reviews)
"Super clean with nice wood flooring. Bath and shower with nice lighting. Quiet, comfortable, and walking distance to restaurant s. Will definitely stop again ."

Reviewed on 18 May 2021

Wingate by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free cancellationReserve now, pay when you stay
The price is £75 per night from 24 May to 24 May
4.5/5Wonderful! (1,173 reviews)
"Easy check in."

Reviewed on 3 May 2021

Country Inn & Suites by Radisson, Winchester, VA
TownePlace Suites by Marriott Front Royal
3 out of 5
5 Caroline Drive, Front Royal, VA
Free cancellationReserve now, pay when you stay
The price is £112 per night from 23 May to 23 May
4.7/5Exceptional! (153 reviews)
"Excellent property. Up to date, immaculate and all amenities including a gym, outside barbecue area and fire pits."

Reviewed on 30 Apr 2021

TownePlace Suites by Marriott Front Royal
TownePlace Suites by Marriott Winchester
2.5 out of 5
170 Getty Ln, Winchester, VA
Free cancellationReserve now, pay when you stay
The price is £79 per night from 13 Jun to 13 Jun
4.3/5Excellent! (297 reviews)
"Staff was great, helped to make my long stay enjoyable."

Reviewed on 4 May 2021

TownePlace Suites by Marriott Winchester
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
Free cancellationReserve now, pay when you stay
The price is £82 per night from 24 May to 24 May
4.4/5Wonderful! (754 reviews)
"The rooms are always very clean and staff is very friendly."

Reviewed on 11 Apr 2021

Fairfield Inn & Suites Strasburg Shenandoah Valley
Don't see what you're looking for?
See all available properties in Old Town Winchester
View all properties
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.