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Top 10 Hotels in Old Town Winchester

Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
Free cancellationReserve now, pay when you stay
£75
per night
15 Dec-16 Dec
4.4/5Wonderful! (664 reviews)

"I loved that the breakfast had vegetarian options - veggie sausage and soy milk. Not many hotels offer this."…"

Reviewed on 11 Nov 2019

Fairfield Inn & Suites Strasburg Shenandoah Valley
Fairfield & Suites by Marriott Winchester
2.5 out of 5
250 Front Royal Pike, Winchester, VA
Free cancellationReserve now, pay when you stay
£65
per night
15 Dec-16 Dec
4.2/5Very Good! (169 reviews)

"Our room was very clean thanks to the attendant named Krista"…"

Reviewed on 24 Nov 2019

Fairfield & Suites by Marriott Winchester
Motel 6 Front Royal, VA
2 out of 5
141 West 15th Street, Front Royal, VA
Free cancellation
£42
per night
10 Dec-11 Dec
3.3/5 (160 reviews)

"It was fine for needing a place to stay and nice that they allow pets at no extra to charge"…"

Reviewed on 6 Dec 2019

Motel 6 Front Royal, VA
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free cancellationReserve now, pay when you stay
£66
per night
15 Dec-16 Dec
4.4/5Excellent! (1,117 reviews)

"Easy location. Great room size. Lot’s of things to do in the area. Great location do. Great stay."…"

Reviewed on 27 Nov 2019

Wingate by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Free cancellationReserve now, pay when you stay
£63
per night
22 Dec-23 Dec
4.3/5Excellent! (1,660 reviews)

"Very nice hotel and extremely friendly staff. We enjoyed our stay at this hotel."…"

Reviewed on 8 Dec 2019

La Quinta Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free cancellationReserve now, pay when you stay
£78
per night
22 Dec-23 Dec
4.7/5Exceptional! (1,104 reviews)

"This is a very elegant, beautifully maintained historic hotel. Our room was pretty and generously sized with a very comfortable bed. The linens were crisp and absolutely spotless. Overall cleanliness of the room and the hotel is very high. We enjoyed our visit and would stay again at this hotel. ..."…"

Reviewed on 6 Dec 2019

The George Washington Hotel, A Wyndham Grand Hotel
Ramada by Wyndham Strasburg
2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Free cancellationReserve now, pay when you stay
£48
per night
25 Dec-26 Dec
3.7/5Good! (914 reviews)

"Breakfast only ser ed until 9:30. Coffee pits and waffle machine were EMPTY!"…"

Reviewed on 26 Nov 2019

Ramada by Wyndham Strasburg
Travelodge by Wyndham Winchester
2 out of 5
160 Front Royal Pike, Winchester, VA
Free cancellationReserve now, pay when you stay
£46
per night
15 Dec-16 Dec
3.5/5Good! (1,656 reviews)

"Quick check in. Complementary breakfast Fine for the night"…"

Reviewed on 9 Nov 2019

Travelodge by Wyndham Winchester
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free cancellationReserve now, pay when you stay
£74
per night
10 Dec-11 Dec
4.5/5Wonderful! (1,708 reviews)

"Tell was in a good location near Highway 81, making it convenient to get off and on my travel. Yes, the breakfast is free, but the coffee isn’t the best."…"

Reviewed on 5 Dec 2019

Country Inn & Suites by Radisson, Winchester, VA
Clarion Inn & Conference Center
2.5 out of 5
711 Millwood Ave, Winchester, VA
Free cancellationReserve now, pay when you stay
£43
per night
22 Dec-23 Dec
3.8/5Good! (846 reviews)

"The mattress and bedding were fabulously comfortable."…"

Reviewed on 5 Dec 2019

Clarion Inn & Conference Center
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Pocket Guide: Old Town Winchester

Visiting Old Town Winchester

Couples looking to get away will find a romantic atmosphere in Old Town Winchester, though all guests will undoubtedly appreciate the shopping, restaurants and bars. Walkable and welcoming, this city will also delight visitors with its cafes, dancing and live music.

  • You'll find Expedia hotels in the surrounding area
  • July is the most expensive month to travel here, whereas January is the most economical
  • Closest major airport is in Washington, DC (IAD-Washington Dulles Intl.), 41.6 mi (67 km) from the city centre

Sightseeing around Old Town Winchester

  • Live music and museums are well-known in the area, and attractions include Bright Box Theater, Old Court House Civil War Museum, and Shenandoah Valley Discovery Museum
  • Families come for attractions such as Wilson's Wild Animal Park, Appleland Sports Center, and Dinosaur Land
  • Notable for its historic sites and landmarks to visit, including George Washington's Office, Stonewall Jackson's Headquarters, and Patsy Cline Historic House
  • Shopping is first class in the area, and Apple Blossom Mall is a favourite spot for retail therapy

Staying in Old Town Winchester

Looking for a romantic getaway or boutique stay? You might like The George Washington Hotel, A Wyndham Grand Hotel.

The George Washington Hotel, A Wyndham Grand Hotel, a favourite with Expedia travellers, has a 4.5 out of 5 user rating.

Dressing for Old Town Winchester

  • Between January and March, you can expect average temperatures of 15°C during the day and -5°C at night
  • From April to June, the average during the day is 29°C, while the average at night is 3°C
  • July to September has daytime averages of 30°C with night-time averages of 10°C
  • Between October and December, you can expect daytime averages of 21°C and nighttime averages of -4°C
  • Average annual rainfall for Old Town Winchester is 977 millimetres

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