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Top 10 Hotels in Winchester

Courtyard by Marriott Winchester
3 out of 5
300 Marriott Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
$93
per night
Jan 26 - Jan 27
4.3/5Excellent! (460 reviews)

"The property is well maintained and staffed with friendly personnel. Only a few nits to pick with room: TV needed resetting and toilet seat was too short for bowl. The small cafe within hotel serves a limited menu and doubles as a cocktail bar in evening and restaurant at other times. We prefer to ..."…"

Reviewed on Nov 30, 2019

Courtyard by Marriott Winchester
Hampton Inn Winchester-University/Mall Area
2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
$93
per night
Feb 2 - Feb 3
4.5/5Wonderful! (777 reviews)

"Perfect location, right off 81. Good breakfast! Staff was a little loud early in the morning (we were on the 4th floor), and it was Sunday morning."…"

Reviewed on Dec 3, 2019

Hampton Inn Winchester-University/Mall Area
Hilton Garden Inn Winchester
3 out of 5
120 Wingate Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
$105
per night
Jan 30 - Jan 31
4.4/5Excellent! (280 reviews)

"Everything great but the shower head was very weak."…"

Reviewed on Nov 11, 2019

Hilton Garden Inn Winchester
Holiday Inn Express Hotel & Suites Winchester
2.5 out of 5
142 Foxridge Ln, Winchester, VA
Free Cancellation
$81
per night
Jan 26 - Jan 27
4.4/5Wonderful! (432 reviews)

"There is construction going on around the property and there is no sign to show where to turn to get to the hotel. I could see it but couldn’t tell where to go to get to the hotel. After speaking with the desk clerk she told me that the county was preventing the hotel from putting a sign out on the ..."…"

Reviewed on Jan 3, 2020

Holiday Inn Express Hotel & Suites Winchester
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free CancellationReserve now, pay when you stay
$76
per night
Jan 28 - Jan 29
4.4/5Excellent! (1,143 reviews)

"Friendliness of the staff and excellent condition of the hotel"…"

Reviewed on Jan 12, 2020

Wingate 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
$93
per night
Jan 28 - Jan 29
4.7/5Exceptional! (1,129 reviews)

"A very lovely hotel. I love the fact the hotel is so close to Old Town Winchester."…"

Reviewed on Jan 17, 2020

The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester
2 out of 5
160 Front Royal Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
$49
per night
Jan 28 - Jan 29
3.5/5Good! (1,667 reviews)

"It was fine for the money we paid, and while it was not the RITZ, it was all we required."…"

Reviewed on Jan 12, 2020

Travelodge 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
$94
per night
Jan 23 - Jan 24
4.3/5Excellent! (1,668 reviews)

"Staff was great, very pet friendly, great location right off 81 and several restaurants and gas stations, nice little shop for soda or snacks in lobby. Decor is nice, very up to date."…"

Reviewed on Jan 10, 2020

La Quinta Inn & Suites 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
$89
per night
Jan 28 - Jan 29
4.5/5Wonderful! (1,738 reviews)

"This was an excellent place to stay. The room was lovely, staff very friendly, excellent breakfast—the only thing that was surprising was a very small, non-HD TV in the room. No hotels have non-HD TVs any more! I understand from the staff that this is an upgrade coming this year, and I would say ..."…"

Reviewed on Jan 21, 2020

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
$51
per night
Feb 4 - Feb 5
3.8/5Good! (872 reviews)

"Nothing not to like! Very Nice and Restaurant on the property."…"

Reviewed on Jan 16, 2020

Clarion Inn & Conference Center
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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.

Visiting Winchester

Families will find kid-friendly activities in Winchester, and visitors give high marks for the shopping and top-notch restaurants. Scenic and vibrant, this city attracts tourists with its theaters and entertainment choices.

  • There are 76 hotels and other accommodations in Winchester
  • The closest major airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), 18 mi (28.9 km) from the city center
  • The next closest is in Washington, DC (IAD-Washington Dulles Intl.), 41.7 mi (67.1 km) away

Sightseeing and Staying in Winchester

Well-known for its theaters, the city's cultural venues include Shenandoah Valley Discovery Museum, Winchester Little Theater, and Museum of the Shenandoah Valley. Families come for attractions such as Dinosaur Land, Wilson's Wild Animal Park, and Rocking S Ranch. The city is notable for its historic sites and landmarks like Patsy Cline Historic House, Holy Cross Abbey, and George Washington's Office.

In Winchester, there are 76 hotels and other lodging accommodations so you'll have a variety of choices for your holiday retreat. These are highly ranked ones based on Expedia user reviews:

  • Wayside Inn - This 3.5-star inn features free breakfast, a restaurant, and free WiFi. It's a favorite with Expedia travelers for its helpful staff and clean, comfortable rooms.
  • Country Inn & Suites by Radisson, Winchester, VA - Our customers like the pool and quiet location at this hotel. This 3-star hotel features free breakfast, an indoor pool, and free WiFi.
  • Fairfield Inn & Suites Strasburg Shenandoah Valley - With a stay at this 2.5-star hotel, guests can enjoy access to free breakfast and an indoor pool, along with in-room LCD TVs. Expedia customers like its breakfast and comfortable, quiet rooms.

One of the top places to see in the surrounding area is Harpers Ferry National Historical Park, 25.2 mi/40.6 km from the heart of the city.

Dressing for Winchester

  • Between January and March, daytime temperatures average 58°F, while nighttime temperatures stay around 23°F
  • From April to June, the average is 85°F during the day and 37°F at night
  • July through September sees average temperatures of 86°F during the day and 49°F at night
  • In October-December, you can expect 71°F as the daytime average and 24°F as the nighttime average
  • Average annual rainfall for Winchester is 38.33 inches
  • July and June are usually the hottest months averaging 84°F, while January and February are usually the coldest with an average temperature of 25°F

How much is a hotel in Winchester?

2 stars to 4 stars hotels in Winchester

Average price based on 2018 bookings on Expedia.com for 1 night / 2 adults.

All prices are shown in USD.

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