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 £102 per night from 23 Aug to 24 Aug
£102
23 Aug - 24 Aug
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 ...
Nostalgia Lane in the heart of the city
Winchester VA
The price is £242 per night from 17 Aug to 18 Aug
£242
17 Aug - 18 Aug
includes taxes & fees
Stay at this apartment in Winchester. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Bright Box Theater and Old ...
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."
Reviewed on 27 Jul 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is £65 per night from 2 Sept to 3 Sept
£65
2 Sept - 3 Sept
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 ...
9.2/10 Wonderful! (1,006 reviews)
"Such a cute and clean hotel! A great place to stay if you need to go to Shenandoah University. Restaurants were within walking distance. The hotel also has a nice continental breakfast but if you’re wanting more there’s a Waffle House right outside the front door."
Reviewed on 16 Aug 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is £79 per night from 23 Aug to 24 Aug
£79
23 Aug - 24 Aug
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 ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is £85 per night from 27 Aug to 28 Aug
£85
27 Aug - 28 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,263 reviews)
"This hotel was full of ants. I booked my hotel through Expedia Hotels.com, and now I have to do all the footwork to get reimbursed for my food that was in sealed bags wrapped up that was completely invaded by aunt. All of my clothing had ants in it. my bed had ants in it. There was four different ..."
Reviewed on 15 Aug 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is £66 per night from 23 Aug to 24 Aug
£66
23 Aug - 24 Aug
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! (1,006 reviews)
"First room I walked into it smelled like a public toilet. I looked in the bathroom and low and behold there is a numer 1 and bonus number 2 awaiting me. I was awarded a new room after I voiced my grievance. Not what I was expecting from a classy joint such as this."
Reviewed on 16 Aug 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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.
Old Town Winchester Travel Guide
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- Welcome to the Ladybug Retreat!
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- Cabin Rentals in Winchester
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- 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
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