Old Town Winchester Hotels, Winchester

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Filter by

Guest rating
Guest rating
Star rating

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

2 restaurants, breakfast, lunch, dinner served; American cuisine
The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1004)
"Very nice hotel "
United States
Paul
The price is AU$220
includes taxes & fees
30 Oct - 31 Oct
The George Washington Hotel, A Wyndham Grand Hotel
Exterior
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
9.2 out of 10, Wonderful, (2177)
"Great hotel"
United States
David
The price is AU$172
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Winchester
Suite, 1 Bedroom
Candlewood Suites Winchester by IHG
Candlewood Suites Winchester by IHG
2.5 star property
8.8 out of 10, Excellent, (523)
"Lots of parking. "
United States
Douglas
The price is AU$149
includes taxes & fees
2 Nov - 3 Nov
Candlewood Suites Winchester by IHG
In-room safe, desk, iron/ironing board, free cots/infant beds
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 star property
8.6 out of 10, Excellent, (1103)
"It's been a great stay so far"
United States
Sabrina
The price is AU$115
includes taxes & fees
3 Nov - 4 Nov
Travelodge by Wyndham Winchester
Exterior
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Great stay value"
United States
Timothy
The price is AU$152
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Winchester Se-Historic Gateway by IHG
Lift
Ramada by Wyndham Strasburg/Shenandoah Valley
Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
8.4 out of 10, Very good, (1000)
"Our stay was fine, convenient location to our planned activities. "
United States
mitchell
The price is AU$128
includes taxes & fees
2 Nov - 3 Nov
Ramada by Wyndham Strasburg/Shenandoah Valley
Indoor pool
Hilton Garden Inn Winchester
Hilton Garden Inn Winchester
3.0 star property
8.8 out of 10, Excellent, (499)
"Great hotel"
United States
DONNA D
The price is AU$167
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Winchester
Snack bar
TRU By Hilton Winchester
TRU By Hilton Winchester
2.5 star property
9.0 out of 10, Wonderful, (727)
"Clean room easy check in/out"
United States
Edward
The price is AU$151
includes taxes & fees
18 Nov - 19 Nov
TRU By Hilton Winchester
Restaurant
The Inn at Charles Town - Hollywood Casino
The Inn at Charles Town - Hollywood Casino
3.0 star property
8.6 out of 10, Excellent, (500)
"Great place to stay to go to the casino"
United States
Sandra
The price is AU$215
includes taxes & fees
10 Nov - 11 Nov
The Inn at Charles Town - Hollywood Casino
Exterior
Holiday Inn Express Winchester South-Stephens City by IHG
Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
8.2 out of 10, Very good, (782)
"Very friendly staff, clean, would definitely stay again "
Canada
Christie
The price is AU$146
includes taxes & fees
7 Nov - 8 Nov
Holiday Inn Express Winchester South-Stephens City by IHG
Exterior
Quality Inn Winchester
Quality Inn Winchester
2.5 star property
9.2 out of 10, Wonderful, (1000)
"Staff was super friendly and accommodating "
United States
John
The price is AU$130
includes taxes & fees
2 Nov - 3 Nov
Quality Inn Winchester
Breakfast area
Econo Lodge Inn & Suites
Econo Lodge Inn & Suites
2.0 star property
5.8 out of 10, (291)
"I loved staying here!"
United States
Whitney
The price is AU$105
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Inn & Suites
Premium bedding, pillow-top beds, blackout curtains, iron/ironing board
Travelodge By Wyndham Charles Town/Harpers Ferry
Travelodge By Wyndham Charles Town/Harpers Ferry
2.0 star property
7.0 out of 10, Good, (253)
"Wasn’t the cleanest but it’s good for a quick stop"
United States
Autumn
The price is AU$117
includes taxes & fees
26 Oct - 27 Oct
Travelodge By Wyndham Charles Town/Harpers Ferry
Exterior
Fairfield Inn & Suites by Marriott Winchester
Fairfield Inn & Suites by Marriott Winchester
2.5 star property
9.0 out of 10, Wonderful, (779)
"Super friendly staff, clean rooms, very convenient. I would definitely stay here again. "
United States
Kathleen
The price is AU$155
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Winchester
Porch
Hampton Inn Winchester-University/Mall Area
Hampton Inn Winchester-University/Mall Area
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! "
United States
Mary
The price is AU$198
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Winchester-University/Mall Area
Property entrance
Baymont by Wyndham Front Royal Near Shenandoah National Park
Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
6.4 out of 10, (898)
"nice for a great stay!!"
United States
Jose
The price is AU$96
includes taxes & fees
9 Nov - 10 Nov
Baymont by Wyndham Front Royal Near Shenandoah National Park
Restaurant
Courtyard by Marriott Winchester
Courtyard by Marriott Winchester
3.0 star property
8.8 out of 10, Excellent, (888)
" Nice hotel"
United States
Grace
The price is AU$179
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott Winchester
Lobby
Spark by Hilton Winchester
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great location close to restaurants "
United States
SILVIA
The price is AU$151
includes taxes & fees
9 Nov - 10 Nov
Spark by Hilton Winchester
Restaurant
Hampton Inn Martinsburg South-Inwood
Hampton Inn Martinsburg South-Inwood
2.5 star property
9.2 out of 10, Wonderful, (629)
"Good location "
United States
Judith
The price is AU$168
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn Martinsburg South-Inwood
Free daily continental breakfast
Quality Inn Stephens City - Winchester South
Quality Inn Stephens City - Winchester South
2.5 star property
8.0 out of 10, Very good, (614)
"Great stay!"
United States
Angela
The price is AU$133
includes taxes & fees
16 Nov - 17 Nov
Quality Inn Stephens City - Winchester South
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.
View all properties
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

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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Friendly staff "
Matt 1-night trip
Posted 3 days ago
Travelodge by Wyndham Winchester

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 12 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.

Explore a world of travel with Expedia