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
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Filter by

Guest rating
Guest rating
Property class

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

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, (1007)
"Wonderful stay! "
The price is AU$221
includes taxes & fees
14 Aug - 15 Aug
The George Washington Hotel, A Wyndham Grand Hotel
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$237
includes taxes & fees
11 Aug - 12 Aug
The Inn at Charles Town - Hollywood Casino
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, (1004)
"Nice, clean, and very well staffed. Would definitely stay there again! "
The price is AU$117
includes taxes & fees
10 Aug - 11 Aug
Rodeway Inn & Suites - Charles Town, WV
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, (1000)
"Nice, quiet, clean place to stay without blowing up your budget."
The price is AU$107
includes taxes & fees
24 Aug - 25 Aug
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, (219)
"The staff is awesome"
The price is AU$103
includes taxes & fees
10 Aug - 11 Aug
Travelodge By Wyndham Charles Town/Harpers Ferry
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (423)
"Excellent, historic, amazing breakfast and hostess"
The price is AU$255
includes taxes & fees
1 Sept - 2 Sept
The Carriage Inn B&B
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$371
includes taxes & fees
10 Aug - 11 Aug
Hillbrook Inn
L'Auberge Provencale Inn & Restaurant
Terrace/patio

L'Auberge Provencale Inn & Restaurant

4.0 star property
9.6 out of 10, Exceptional, (167)
"Beautiful historic property well maintained and on the way to Skyline Drive. Breakfast was divine!"
The price is AU$388
includes taxes & fees
11 Aug - 12 Aug
L'Auberge Provencale Inn & Restaurant
Hampton Inn Martinsburg South-Inwood
Restaurant

Hampton Inn Martinsburg South-Inwood

2.5 star property
9.2 out of 10, Wonderful, (601)
"The property was very clean and the breakfast was excellent."
The price is AU$174
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Martinsburg South-Inwood
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$179
includes taxes & fees
8 Aug - 9 Aug
TownePlace Suites by Marriott Winchester
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, (676)
"Great breakfast! "
The price is AU$194
includes taxes & fees
10 Aug - 11 Aug
SpringHill Suites by Marriott Winchester
APM Inn & Suites
Interior

APM Inn & Suites

2.0 star property
6.6 out of 10, (319)
"very nice and cheap place to stay"
The price is AU$94
includes taxes & fees
29 Aug - 30 Aug
APM Inn & Suites
Baymont by Wyndham Front Royal Near Shenandoah National Park
Property entrance

Baymont by Wyndham Front Royal Near Shenandoah National Park

2.5 star property
6.4 out of 10, (856)
"We had a great stay. Clean and staff was friendly "
The price is AU$96
includes taxes & fees
1 Sept - 2 Sept
Baymont by Wyndham Front Royal Near Shenandoah National Park
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, (791)
"A good solid Hampton inn, close to historic downtown with lots of restaurants and bars."
The price is AU$184
includes taxes & fees
14 Aug - 15 Aug
Hampton Inn Winchester N/Conference Center, VA
Microtel Inn & Suites by Wyndham Winchester
Lobby

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1317)
"Pleasant stay"
The price is AU$132
includes taxes & fees
1 Sept - 2 Sept
Microtel Inn & Suites by Wyndham Winchester
Candlewood Suites Winchester by IHG
Suite, 1 Bedroom

Candlewood Suites Winchester by IHG

2.5 star property
8.8 out of 10, Excellent, (488)
"Lovely stay. Would stay again! "
The price is AU$137
includes taxes & fees
7 Sept - 8 Sept
Candlewood Suites Winchester by IHG
Quality Inn Winchester
Exterior

Quality Inn Winchester

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great place , great front desk staff, super clean & very quiet"
The price is AU$127
includes taxes & fees
1 Sept - 2 Sept
Quality Inn Winchester
Days Inn by Wyndham Winchester
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Days Inn by Wyndham Winchester

2.0 star property
6.6 out of 10, (432)
"I was unable to stay at this location and had to cancel with the hotel."
The price is AU$110
includes taxes & fees
10 Aug - 11 Aug
Days Inn by Wyndham Winchester
Super 8 by Wyndham Front Royal
Lobby

Super 8 by Wyndham Front Royal

2.0 star property
7.4 out of 10, Good, (1001)
"Convenient to Skyline Drive in Shenandoah National Park."
The price is AU$113
includes taxes & fees
13 Aug - 14 Aug
Super 8 by Wyndham Front Royal
TRU By Hilton Winchester
Snack bar

TRU By Hilton Winchester

2.5 star property
9.0 out of 10, Wonderful, (690)
"I stop every time I travel south and it is consistently a great hotel and staff is phenomenal"
The price is AU$162
includes taxes & fees
1 Sept - 2 Sept
TRU By Hilton 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

10/10 Excellent
"little hard to find as its sits off the main road. night auditor was friendly and professional"
William 1-night trip
Posted 20 hours ago
Sleep Inn & Suites Winchester near University

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 10 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.