Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is £111 per night from 21 Jul to 22 Jul
£111
21 Jul - 22 Jul
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,006 reviews)
"Very charming historic hotel. Close to very nice restaurants and tourist District."
Reviewed on 4 Jul 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is £76 per night from 19 Jul to 20 Jul
£76
19 Jul - 20 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,008 reviews)
"Good location but floor was sticky in room and no closets, just open hooks."
Reviewed on 4 Jul 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is £73 per night from 26 Jul to 27 Jul
£73
26 Jul - 27 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,003 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."
Reviewed on 28 Jun 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is £76 per night from 26 Jul to 27 Jul
£76
26 Jul - 27 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,006 reviews)
"Comfortable clean room. Bathroom could use an upgrade. Shower head flow could not be changed to a softer setting. Also one of the few hotel chains that doesn’t offer a free breakfast. At $10 pp, Wawa is not far and has good food and coffee."
Reviewed on 3 Jul 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is £80 per night from 6 Jul to 7 Jul
£80
6 Jul - 7 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,428 reviews)
"We live close by to the hotel and our air conditioner is not working during this heat wave. This was our second stay because of how friendly the staff is as well as being a clean property. The breakfast has multiple choices. Great hotel especially for the price."
Reviewed on 3 Jul 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
Fully refundableReserve now, pay when you stay
The price is £67 per night from 19 Jul to 20 Jul
£67
19 Jul - 20 Jul
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very good! (1,004 reviews)
"Hotel is starting to run down, needs some remodeling."
Reviewed on 1 Jul 2026
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 for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester
Photo by Fernando Begay
Open Photo by Fernando Begay
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.
Old Town Winchester Travel Guide
Explore a world of travel with Expedia
- Hotels near Aspen Dale Winery at the Barn
- Berryville Hotels
- Bluemont Hotels
- Loudoun County Hotels
- A nice and cozy home ! Close to almost everything!
- Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
- Doubletree by Hilton Front Royal Blue Ridge Shadows
- New
- Shenandoah Twilight
- Shenandoah Mountain House
- The Foxwood Cabin
- The Trillium Cabin
- Front Royal Hotels
- Cheap Hotels in Leesburg
- Gay-Friendly Hotels in Leesburg
- The Manor at Courtland Farm
- Leesburg Hotels
- Skyland
- Marshall Hotels
- Hotels with Hot Tubs in Old Town Winchester
- Old Town Winchester Hotels
- Orlean Hotels
- Welcome to the Ladybug Retreat!
- Paris Hotels
- A Restored Wagon Barn On A 1790's Farm.
- Hillandale Farmhouse circa 1774
- Falling Leaf Cabin Rustic Charm With Modern Decor! Newly Renovated Kitchen!
- Star view cabin
- Riverton Hotels
- Round Hill Hotels
- Star Tannery Hotels
- Washington Hotels
- Farmhouse at Paige's Pit Stop
- Cabin Rentals in Winchester
- Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
- Cheap Hotels in Winchester
- Budget Inn
- Hampton Inn Front Royal
- Holiday Inn Express Hotel & Suites Winchester by IHG
- Holiday Inn Express Winchester South
- Holiday Inn Winchester Se
- L'auberge Provencale Inn & Restaurant
- Luxury Hotels in Winchester
- Oyo Rooms Hotels in Winchester
- Quality Inn Winchester
- Spark by Hilton Winchester
- Towneplace Suites by Marriott Front Royal
- Winery Hotels in Winchester
- Winchester Hotels
- Flights to Front Royal
- Flights to Middleburg
- Flights to Paris
- Flights to Syria
- Flights to Washington Dulles Intl.
- Flights to Winchester
- Flights to Woodstock
- Flights from Washington Dulles Intl.
- Flights from Winchester Regional
- British Airways London (LHR) to Washington (IAD) flights
- United London (LHR) to Washington (IAD) flights
- Flights from Round Hill
- Flights from Star Tannery
- Flights from Front Royal
- Flights from Leesburg
- Flights from Aberdeen (APG) to Winchester (WGO)
- Flights from Newcastle (BEO) to Winchester (WGO)
- Flights from Belfast (BFS) to Winchester (WGO)
- Flights from Birmingham (BHM) to Winchester (WGO)
- Flights from Edinburgh (EDI) to Winchester (WGO)
- Flights from Glasgow (GLA) to Winchester (WGO)
- Flights from Seoul (ICN) to Winchester (WGO)
- Flights from Los Angeles (LAX) to Winchester (WGO)
- Flights from London (LHR) to Washington (IAD)
- Flights from London (LON) to Winchester (WGO)
- Flights from Manchester (MAN) to Washington (IAD)
- Flights from Chicago (ORD) to Winchester (WGO)
- Flights from Norfolk (ORF) to Washington (IAD)
