Find hotels in Old Town Winchester, Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Discover Old Town Winchester hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Blue Ridge Motel

2.0 star property
7.0 out of 10, Good, (128)
"Inexpensive for a 1 night stopover. Dated rooms and limited facilities . Comfy sleep though"
Blue Ridge Motel

Relax Inn Motel

2.0 star property
8.2 out of 10, Very Good, (241)
"Clean, and nice rooms, friendly staff"
The price is NT$1,894
NT$2,109 total
includes taxes & fees
Aug 31 - Sep 1
Relax Inn Motel

Twi-Lite Inn

2.0 star property
8.2 out of 10, Very Good, (520)
"Great pool and quiet area to stay in"
The price is NT$2,446
NT$2,722 total
includes taxes & fees
Sep 3 - Sep 4
Twi-Lite Inn

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1018)
"Wonderful stay! "
The price is NT$3,822
NT$4,331 total
includes taxes & fees
Sep 1 - Sep 2
The George Washington Hotel, A Wyndham Grand Hotel

Travelodge By Wyndham Charles Town/Harpers Ferry

2.0 star property
7.0 out of 10, Good, (229)
"The staff is awesome"
The price is NT$1,843
NT$2,083 total
includes taxes & fees
Sep 1 - Sep 2
Travelodge By Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

2.0 star property
8.0 out of 10, Very Good, (1000)
"all our visits here have been good"
The price is NT$2,012
NT$2,274 total
includes taxes & fees
Sep 3 - Sep 4
Days Inn by Wyndham Charles Town/Harpers Ferry

ANS Inn & Suites

2.0 star property
7.6 out of 10, Good, (65)
"Everyone here was so friendly. The cats in the lobby to greet guests was awesome."
The price is NT$2,047
NT$2,442 total
includes taxes & fees
Sep 9 - Sep 10
ANS Inn & Suites

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1005)
"We have stayed here many of times love it!"
The price is NT$2,017
NT$2,244 total
includes taxes & fees
Sep 10 - Sep 11
Super 8 by Wyndham Front Royal

Days Inn by Wyndham Winchester

2.0 star property
6.4 out of 10, (439)
"I was unable to stay at this location and had to cancel with the hotel."
The price is NT$2,007
NT$2,184 total
includes taxes & fees
Sep 7 - Sep 8
Days Inn by Wyndham Winchester

APM Inn & Suites

2.0 star property
6.6 out of 10, (328)
"very nice and cheap place to stay"
The price is NT$1,788
NT$2,026 total
includes taxes & fees
Aug 31 - Sep 1
APM Inn & Suites

L'Auberge Provencale Inn & Restaurant

4.0 star property
9.6 out of 10, Exceptional, (172)
"Wonderful staff and service!"
The price is NT$9,136
NT$10,077 total
includes taxes & fees
Sep 8 - Sep 9
L'Auberge Provencale Inn & Restaurant

Gateway Inn

2.0 star property
5.0 out of 10, (9)
"Bare bones, but perfectly adequate hotel if you just want a bed, a hot shower and a little TV (didn’t check the WIFI, but Verizon worked fine in the room anyway). Easy parking, friendly front desk person. I’d stay again. (Fridge and microwave were also handy). "
The price is NT$1,955
NT$2,176 total
includes taxes & fees
Sep 6 - Sep 7
Gateway Inn

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
8.8 out of 10, Excellent, (1006)
"Always stay here. Quiet , clean and 2 mins from casino "
The price is NT$2,227
NT$2,517 total
includes taxes & fees
Sep 1 - Sep 2
Rodeway Inn & Suites - Charles Town, WV

Wayside Inn

3.5 star property
9.2 out of 10, Wonderful, (404)
"Rooms and property were beautiful. Wish they provided garbage cans and ash trays for outdoor seating. "
The price is NT$2,889
NT$3,492 total
includes taxes & fees
Aug 31 - Sep 1
Wayside Inn

Super 8 by Wyndham Winchester VA

2.0 star property
6.2 out of 10, (605)
"Easy to book."
The price is NT$1,760
NT$1,915 total
includes taxes & fees
Sep 15 - Sep 16
Super 8 by Wyndham Winchester VA

Motel 6 Front Royal, VA

2.0 star property
6.8 out of 10, (484)
"Quiet "
The price is NT$1,741
NT$1,938 total
includes taxes & fees
Sep 14 - Sep 15
Motel 6 Front Royal, VA

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 star property
6.4 out of 10, (869)
"nice for a great stay!!"
The price is NT$1,767
NT$1,967 total
includes taxes & fees
Sep 24 - Sep 25
Baymont by Wyndham Front Royal Near Shenandoah National Park

Quality Inn Stephens City - Winchester South

2.5 star property
8.0 out of 10, Very Good, (600)
"Great stay!"
The price is NT$2,166
NT$2,357 total
includes taxes & fees
Sep 15 - Sep 16
Quality Inn Stephens City - Winchester South

Quality Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Great place , great front desk staff, super clean & very quiet"
The price is NT$2,313
NT$2,516 total
includes taxes & fees
Sep 21 - Sep 22
Quality Inn Winchester

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1006)
"Fantastic stay, thanks!"
The price is NT$3,092
NT$3,502 total
includes taxes & fees
Sep 7 - Sep 8
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Expedia customer reviews, The George Washington Hotel, A Wyndham Grand Hotel is the highest ranked property 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 11 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.