Old Town Winchester Hotels, 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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Aug - 14 Aug
Tomorrow
14 Aug - 15 Aug
This weekend
15 Aug - 17 Aug
Next weekend
22 Aug - 24 Aug

Filter by

Guest rating
Guest rating
Property class

357 Cheap Hotels in Old Town Winchester - Specials, Reviews, & Last Minute Deals

Country Inn & Suites by Radisson, Winchester, VA
Lobby

Country Inn & Suites by Radisson, Winchester, VA

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great place to stay!"
The price is AU$159
includes taxes & fees
17 Aug - 18 Aug
Country Inn & Suites by Radisson, Winchester, VA
Courtyard by Marriott Winchester
Restaurant

Courtyard by Marriott Winchester

3.0 star property
8.8 out of 10, Excellent, (857)
"Beds were comfortable and staff were very nice."
The price is AU$169
includes taxes & fees
29 Aug - 30 Aug
Courtyard by Marriott Winchester
Comfort Inn & Suites Winchester
Exterior

Comfort Inn & Suites Winchester

2.5 star property
9.4 out of 10, Exceptional, (1008)
"Perfect stay for our family while on the road"
The price is AU$161
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Winchester
The George Washington Hotel, A Wyndham Grand Hotel
2 restaurants, breakfast, lunch, dinner served; American cuisine

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1004)
"Wonderful stay! "
The price is AU$205
includes taxes & fees
31 Aug - 1 Sept
The George Washington Hotel, A Wyndham Grand Hotel
Rodeway Inn & Suites - Charles Town, WV
2 bars/lounges, sports bar

Rodeway Inn & Suites - Charles Town, WV

2.0 star property
8.8 out of 10, Excellent, (1005)
"Nice, clean, and very well staffed. Would definitely stay there again! "
The price is AU$117
includes taxes & fees
17 Aug - 18 Aug
Rodeway Inn & Suites - Charles Town, WV
The Inn at Charles Town - Hollywood Casino
Restaurant

The Inn at Charles Town - Hollywood Casino

3.0 star property
8.6 out of 10, Excellent, (479)
"Easy to get to, close to casino. Dining options nearby. Staff is friendly, especially the ladies that handle breakfast."
The price is AU$236
includes taxes & fees
18 Aug - 19 Aug
The Inn at Charles Town - Hollywood Casino
Days Inn by Wyndham Charles Town/Harpers Ferry
Premium bedding, pillow-top beds, desk, blackout curtains

Days Inn by Wyndham Charles Town/Harpers Ferry

2.0 star property
8.0 out of 10, Very good, (1001)
"Nice, quiet, clean place to stay without blowing up your budget."
The price is AU$103
includes taxes & fees
31 Aug - 1 Sept
Days Inn by Wyndham Charles Town/Harpers Ferry
Travelodge By Wyndham Charles Town/Harpers Ferry
Premium bedding, pillow-top beds, blackout curtains, iron/ironing board

Travelodge By Wyndham Charles Town/Harpers Ferry

2.0 star property
7.0 out of 10, Good, (222)
"The staff is awesome"
The price is AU$103
includes taxes & fees
17 Aug - 18 Aug
Travelodge By Wyndham Charles Town/Harpers Ferry
Hillbrook Inn
Property amenity

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (668)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
The price is AU$373
includes taxes & fees
17 Aug - 18 Aug
Hillbrook Inn
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (424)
"Excellent, historic, amazing breakfast and hostess"
The price is AU$271
includes taxes & fees
14 Aug - 15 Aug
The Carriage Inn B&B
L'Auberge Provencale Inn & Restaurant
Terrace/patio

L'Auberge Provencale Inn & Restaurant

4.0 star property
9.6 out of 10, Exceptional, (170)
"Beautiful historic property well maintained and on the way to Skyline Drive. Breakfast was divine!"
The price is AU$391
includes taxes & fees
14 Aug - 15 Aug
L'Auberge Provencale Inn & Restaurant
Hampton Inn Front Royal
Exterior

Hampton Inn Front Royal

2.5 star property
9.0 out of 10, Wonderful, (1004)
"Great stay"
The price is AU$187
includes taxes & fees
24 Aug - 25 Aug
Hampton Inn Front Royal
Hampton Inn Martinsburg South-Inwood
Restaurant

Hampton Inn Martinsburg South-Inwood

2.5 star property
9.2 out of 10, Wonderful, (603)
"The property was very clean and the breakfast was excellent."
The price is AU$174
includes taxes & fees
24 Aug - 25 Aug
Hampton Inn Martinsburg South-Inwood
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Bar (on property)

DoubleTree by Hilton Front Royal Blue Ridge Shadows

4.0 star property
9.0 out of 10, Wonderful, (1001)
"Fantastic stay, thanks!"
The price is AU$176
includes taxes & fees
24 Aug - 25 Aug
DoubleTree by Hilton Front Royal Blue Ridge Shadows
SpringHill Suites by Marriott Winchester
1 bedroom, pillow-top beds, desk, laptop workspace

SpringHill Suites by Marriott Winchester

2.5 star property
9.4 out of 10, Exceptional, (687)
"The hotel was clean, staff was great and breakfast was great."
The price is AU$193
includes taxes & fees
17 Aug - 18 Aug
SpringHill Suites by Marriott Winchester
TownePlace Suites by Marriott Winchester
In-room safe, desk, iron/ironing board, bed sheets

TownePlace Suites by Marriott Winchester

3.0 star property
8.8 out of 10, Excellent, (453)
"Ten outta ten would stay here again and again and again! Plenty of eatery options nearby, great staff and super quiet! Clean and fun! Had an awesome time!"
The price is AU$178
includes taxes & fees
14 Aug - 15 Aug
TownePlace Suites by Marriott Winchester
Hampton Inn Winchester N/Conference Center, VA
Snack bar

Hampton Inn Winchester N/Conference Center, VA

2.5 star property
9.2 out of 10, Wonderful, (792)
"A good solid Hampton inn, close to historic downtown with lots of restaurants and bars."
The price is AU$190
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Winchester N/Conference Center, VA
Super 8 by Wyndham Front Royal
Lobby

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1002)
"Convenient to Skyline Drive in Shenandoah National Park."
The price is AU$99
includes taxes & fees
1 Sept - 2 Sept
Super 8 by Wyndham Front Royal
Quality Inn Winchester
Exterior

Quality Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Bed was comfortable, room was clean and very spacious "
The price is AU$126
includes taxes & fees
1 Sept - 2 Sept
Quality Inn Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Exterior

Holiday Inn Winchester Se-Historic Gateway by IHG

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great location,the hotel was very nice and the breakfast was great."
The price is AU$153
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Winchester Se-Historic Gateway by IHG
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.

Our guide on where to stay in Old Town Winchester

Find the best Old Town Winchester areas for the activities you enjoy most.
Winchester Historic District map

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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Bed comfy, dinner delicious. Lovely ambiance in lobby and enjoyed pool. "
Laurie 1-night trip
Posted 3 days ago
The George Washington Hotel, A Wyndham Grand Hotel

Frequently asked questions

What is Old Town Winchester like?

Old Town Winchester is an historic neighbourhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Make sure that you visit Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighbourhood.

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 should I expect to find in the Old Town Winchester area?

With 11 Expedia hotels and other accommodation options 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, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to review the best deals available in Old Town Winchester.

What is there to do around this Winchester neighbourhood?

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 worth a visit in the neighbourhood. 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.