A white neoclassical building with columns, an American flag, and a clock tower.

Find hotels in Old Town Winchester, Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Old Town Winchester hotels

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,008 reviews)
"Clean charming place to stay in the area "
United States
Elizabeth
The price is ¥21,088
¥23,893 total
includes taxes & fees
Jul 13 - Jul 14
The George Washington Hotel, A Wyndham Grand Hotel

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
24.4 km from Old Town Winchester
9.6 out of 10, Exceptional, (584 reviews)
"Great location to explore the Shenandoah mountains . Lots of shops and eateries."
United States
katherine
The price is ¥22,482
¥25,121 total
includes taxes & fees
Jul 27 - Jul 28
TownePlace Suites by Marriott Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean , close to National park"
United States
Robert
The price is ¥21,088
¥23,470 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn Front Royal

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
14.1 km from Old Town Winchester
9.6 out of 10, Exceptional, (178 reviews)
"Everything about this special place is incredible."
United States
James
The price is ¥36,246
¥39,979 total
includes taxes & fees
Jun 30 - Jul 1
L'Auberge Provencale Inn & Restaurant

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,010 reviews)
"Excellent hotel, very clean, nice beds."
United States
Sarat
The price is ¥13,992
¥15,852 total
includes taxes & fees
Jul 26 - Jul 27
Spark by Hilton Winchester

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
21.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"Easy parking, great location. The room was quiet and very comfortable."
United States
Joe
The price is ¥20,782
¥22,924 total
includes taxes & fees
Jul 13 - Jul 14
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (679 reviews)
"Lovely Luxury with a spacious sunset suite. Very comfortable bed and sofa. Wish there were one or more sofa tables. staff were delightful, will definitely come again. Please add a cafe for guests not wanting a large expensive dinner. Breakfast Food was very good. Kitchen well equipped for beverage and snack storage, and very clean."
United States
Margaret
The price is ¥23,135
¥29,955 total
includes taxes & fees
Jul 19 - Jul 20
Hillbrook Inn

Wayside Inn

Wayside Inn
3.5 star property
19.8 km from Old Town Winchester
9.2 out of 10, Wonderful, (438 reviews)
"Nice historic place"
United States
Donna
The price is ¥19,652
¥23,292 total
includes taxes & fees
Jun 30 - Jul 1
Wayside Inn

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
24.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"It was a nice hotel for an over night stay. The room took a while to cool down but the overall stay was great."
United States
Joni
The price is ¥19,085
¥21,243 total
includes taxes & fees
Jul 5 - Jul 6
Fairfield Inn & Suites Strasburg Shenandoah Valley

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.2 out of 10, Wonderful, (988 reviews)
"Great hotel good location"
United States
Federico
The price is ¥13,726
¥15,141 total
includes taxes & fees
Jul 5 - Jul 6
TRU By Hilton Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
12.4 km from Old Town Winchester
8.2 out of 10, Very Good, (860 reviews)
" Breakfast was delicious!"
Canada
Betty
The price is ¥15,527
¥16,894 total
includes taxes & fees
Jul 2 - Jul 3
Holiday Inn Express Winchester South-Stephens City by IHG

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
7.8 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,119 reviews)
"Decent accommodations, friendly staff."
United States
Juliet
The price is ¥16,310
¥17,746 total
includes taxes & fees
Jul 21 - Jul 22
Comfort Inn & Suites Winchester

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
2.1 km from Old Town Winchester
9.2 out of 10, Wonderful, (905 reviews)
"The room was very clean and the front desk staffs were very nice."
United States
Angelina
The price is ¥18,435
¥20,886 total
includes taxes & fees
Jul 5 - Jul 6
Hampton Inn Winchester N/Conference Center, VA

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
3 km from Old Town Winchester
8.8 out of 10, Excellent, (511 reviews)
"Nice studio. Our only complaint was the mattress which was to soft"
United States
Judith
The price is ¥18,285
¥19,894 total
includes taxes & fees
Jun 30 - Jul 1
TownePlace Suites by Marriott Winchester

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
29.7 km from Old Town Winchester
8.6 out of 10, Excellent, (1,002 reviews)
"Wonderful place to stay"
United States
Jeremiah
The price is ¥12,371
¥13,978 total
includes taxes & fees
Jul 13 - Jul 14
Rodeway Inn & Suites Charles Town

Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
3.6 km from Old Town Winchester
8.4 out of 10, Very Good, (7 reviews)
"There was no shampoo nor shower gel and the shower was cool water. Takes 5 minutes to even get lukewarm water. No one at front desk to check out so ??? "
United States
Timothy
The price is ¥15,970
¥18,093 total
includes taxes & fees
Jul 29 - Jul 30
Home2 Suites By Hilton Winchester

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
30.4 km from Old Town Winchester
7.6 out of 10, Good, (1,002 reviews)
"room was clean and staff was friendly"
United States
Carol
The price is ¥10,837
¥12,061 total
includes taxes & fees
Jul 5 - Jul 6
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
25.8 km from Old Town Winchester
8.2 out of 10, Very Good, (1,007 reviews)
"Everything thing was good and there is a Mexican bar and restaurant attached to hotel."
United States
Ronald
The price is ¥13,828
¥15,390 total
includes taxes & fees
Jul 5 - Jul 6
Ramada by Wyndham Strasburg/Shenandoah Valley

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
30 km from Old Town Winchester
8.6 out of 10, Excellent, (588 reviews)
"Property was clean and staff was helpful."
United States
Lee
The price is ¥17,258
¥20,945 total
includes taxes & fees
Jul 1 - Jul 2
The Inn at Charles Town - Hollywood Casino

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
5.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (867 reviews)
"Staff was very helpful, room was better than expected, pool was fantastic. Nice fitness center too."
United States
Chris
The price is ¥18,361
¥19,978 total
includes taxes & fees
Jul 5 - Jul 6
SpringHill Suites by Marriott 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.

Where to stay in Old Town Winchester

Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Top Old Town Winchester Hotel Reviews

Frequently asked questions

What is Old Town Winchester like?
Old Town Winchester is a historic neighborhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Be sure to check out Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighborhood.
Where is the best place to stay in Old Town Winchester?
Based on our traveler data, The George Washington Hotel, A Wyndham Grand Hotel is one of the top choices for your stay in Old Town Winchester. This hotel offers a full-service spa and 2 restaurants.
How many hotels can I expect to find in the Old Town Winchester area?
With 13 Expedia hotels and other accommodations in Old Town Winchester to choose from, this is a good starting point for exploring the greater Winchester area.
If I need to cancel my hotel reservation in Old Town Winchester, will I receive a refund?
Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get top deals in Old Town Winchester.
Where can I learn more about changing or cancelling my trip to Old Town Winchester?
For additional details about rescheduling or cancelling your trip to Old Town Winchester, head over to our customer service page.
What is there to do around this Winchester neighborhood?
Sights like Bright Box Theater and Old Court House Civil War Museum can be part of your cultural tour of Old Town Winchester. Shenandoah Valley Discovery Museum and Handley Regional Library are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include George Washington's Office, Mt Hebron Cemetery, and Winchester Little Theater. When you're sightseeing in Winchester, Stonewall Jackson's Headquarters and Patsy Cline Historic House are also worth a stop.