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Find Hotels in Winchester, VA

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  Just Like Heaven Carriage House
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4.42 mi from city center
4.8/5Exceptional! (15 reviews)
Anniversary

"My husband and I had a wonderful relaxing stay. Ramana was a fantastic hostess. The assortment of organic teas was an extra benefit!! The view from the front porch....just what we needed to relate and relax!"…"

Reviewed on Oct 3, 2020

Just Like Heaven Carriage House
City Charmer Near Historic Oldtown Winchester
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4.65 mi from city center
5/5Exceptional! (29 reviews)
You'll be "Charmed"

""The City Charmer" is the perfect place for your Winchester stay! It is centrally located and convenient to interstates and the downtown pedestrian mall. The house is clean, cozy and has everything you need whether you want to use it as a "home base'" to explore the area or just relax on the amazing ..."…"

Reviewed on Feb 20, 2021

City Charmer Near Historic Oldtown Winchester
APM Brookfield
3 out of 5
500 Brookfield Dr, Winchester, VA
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5.26 mi from city center
5/5Exceptional! (1 review)
his place is awesome

"This place is awesome clean and the staff are so friendly. This is the only hotel we stay at now"…"

Reviewed on Feb 17, 2020

APM Brookfield
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Travelodge by Wyndham Winchester
2 out of 5
160 Front Royal Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $51 per night from Feb 28 to Mar 1
5.43 mi from city center
3.6/5Good! (988 reviews)

"The room was spacious, clean, and tidy. The tv was a nice size and the bed was pretty comfortable as well."…"

Reviewed on Feb 4, 2021

Travelodge by Wyndham Winchester
Days Inn by Wyndham Winchester
2 out of 5
1593 Martinsburg Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $53 per night from Mar 5 to Mar 6
4.99 mi from city center
3.4/5 (166 reviews)

"Very simple, no frills, but very clean and efficient. Worth the money and I will stay there again."…"

Reviewed on Feb 14, 2021

Days Inn by Wyndham Winchester
SpringHill Suites by Marriott Winchester
2.5 out of 5
280 MARKET STREET, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $89 per night from Feb 27 to Feb 28
5.55 mi from city center
4.7/5Exceptional! (57 reviews)

"Very easy to find Close to great places to eat! Lovely staff!"…"

Reviewed on Feb 22, 2021

SpringHill Suites by Marriott Winchester
Colonial Getaway Near Old Town Historic Winchester
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6.38 mi from city center
4.9/5Exceptional! (17 reviews)
Great house in Winchester

"You can tell the owner takes great pride in their house. From a welcoming message on the kitchen board to holiday decorations to nice little details like plenty of Kerrigan pods on hand it was a joy to stay here. It easily fit our family of 7 and provided a wonderful home away from home. It was super ..."…"

Reviewed on Dec 30, 2020

Colonial Getaway Near Old Town Historic Winchester
Wingate by Wyndham Winchester
2.5 out of 5
150 Wingate Dr, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $80 per night from Mar 7 to Mar 8
4.76 mi from city center
4.4/5Excellent! (1,000 reviews)

"Clean room. Staff was pleasant. Paid for breakfast but was only offered a bag one because of COVID."…"

Reviewed on Feb 25, 2021

Wingate by Wyndham Winchester
ANS Inn & Suites
2 out of 5
2649 Valley Ave, Winchester, VA
The price is $54 per night from Feb 27 to Feb 28
4.59 mi from city center
3.8/5Good! (49 reviews)

"Decent hotel. Clean and was near everything else."…"

Reviewed on Jul 20, 2020

ANS Inn & Suites
Super 8 by Wyndham Winchester VA
2 out of 5
1077 Millwood Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $53 per night from Feb 28 to Mar 1
5.61 mi from city center
3.2/5 (348 reviews)
enough for the price

"There was 3 sheriff's cars and 6 cops inside, didn't smell the greatest, but for the price and a quick stay it was good, definitely needs some work"…"

Reviewed on Jun 27, 2020

Super 8 by Wyndham Winchester VA
Country Inn & Suites by Radisson, Winchester, VA
3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $76 per night from Mar 7 to Mar 8
6.54 mi from city center
4.6/5Wonderful! (1,195 reviews)

"Nice room, pleasant staff, nearby restaurants and other amenities."…"

Reviewed on Jan 28, 2021

Country Inn & Suites by Radisson, Winchester, VA
APM Executive Suites
3 out of 5
2971 Valley Ave, Winchester, VA
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5.01 mi from city center
4/5Very Good! (15 reviews)

"It was a convenient location for us to catch up on old times considering the corona restrictions."…"

Reviewed on Apr 28, 2020

APM Executive Suites
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
The price is $89 per night from Mar 7 to Mar 8
4.14 mi from city center
4.6/5Exceptional! (977 reviews)

"Room was nice. Would have been nice if more amenities were open."…"

Reviewed on Feb 11, 2021

The George Washington Hotel, A Wyndham Grand Hotel
Red Roof Inn Winchester, VA
2 out of 5
991 Millwood Pike, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $60 per night from Feb 27 to Feb 28
5.51 mi from city center
3.5/5Good! (994 reviews)
Clean but Not Clean???

"Supposedly a Deluxe Room. But it was very inexpensive so expectations were not real high. Pealing pain in tub and shower not attractive but appeared clean so not to bad. Room 10. Large Mold spot just behind the toilet tank bowl was what made the room bad. So obvious why would anyone think it was ..."…"

Reviewed on Oct 26, 2020

Red Roof Inn Winchester, VA
Motel 6 Winchester, VA
2 out of 5
2951 Valley Avenue, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $55 per night from Feb 28 to Mar 1
4.98 mi from city center
4/5Very Good! (870 reviews)

"Met my needs due to a storm front rolling in. I would recommend this to my family."…"

Reviewed on Feb 9, 2021

Motel 6 Winchester, VA
TownePlace Suites by Marriott Winchester
2.5 out of 5
170 Getty Ln, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $79 per night from Feb 27 to Feb 28
5.72 mi from city center
4.3/5Excellent! (290 reviews)

"It was quiet. Seemed like we were the only guests here."…"

Reviewed on Feb 11, 2021

TownePlace Suites by Marriott Winchester
Sleep Inn & Suites
2.5 out of 5
140 Costello Dr, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $74 per night from Feb 28 to Mar 1
5.5 mi from city center
4.2/5Excellent! (581 reviews)

"Staff was wonderful and very helpful...Catered to our every need as we are handicapped..Fern was absolutely a joy to talk to and very informative with our questions"…"

Reviewed on Jan 11, 2021

Sleep Inn & Suites
Courtyard by Marriott Winchester
3 out of 5
300 Marriott Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $76 per night from Mar 2 to Mar 3
2.19 mi from city center
4.4/5Excellent! (555 reviews)

"Loved how modern the property looked and felt, my friend and mr enjoyed an extra 30 minutes of pool time after it closed."…"

Reviewed on Feb 16, 2021

Courtyard by Marriott Winchester
APM Inn & Suites
2 out of 5
1347 Berryville Ave, Winchester, VA
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5.37 mi from city center
3.6/5Good! (46 reviews)
Customer service

"Got there 8 on no one was there door was locked phone number didn't work once I asked a passed by I had a reservation she went into the motel to get someone someone came up and chked me inn while chkimg out me and my wife wanted to leave at 7 am well no one is here to chk u out to 8 am and there ..."…"

Reviewed on Oct 13, 2020

APM Inn & Suites
Hilton Garden Inn Winchester
3 out of 5
120 Wingate Drive, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $109 per night from Feb 27 to Feb 28
4.84 mi from city center
4.4/5Excellent! (309 reviews)

"Clean, roomy, helpful and friendly staff, centrally located."…"

Reviewed on Jan 31, 2021

Hilton Garden Inn Winchester
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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

Frequently asked questions

Where is the best place to stay in Winchester?
L’Auberge Provencale is a favorite property for Expedia customers. This 4-star hotel offers free breakfast and a restaurant. Other top choices based on reviews include TownePlace Suites by Marriott Front Royal and SpringHill Suites by Marriott Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! The majority of hotel reservations are refundable if you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Put your dates in and click on “Search”, then use the “free cancellation” filter to get the best deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To find more details about updating your trip to Winchester or cancelling it, click here.
What's the best budget-friendly hotel in Winchester?
Based on reviews, Quality Inn is a popular 2.5-star hotel for our travelers looking for an economical choice, and features free breakfast and free WiFi. Other options to stay on the cheap include Days Inn by Wyndham Winchester and Sleep Inn & Suites.
What's the best place to stay when traveling with kids to Winchester?
Country Inn & Suites by Radisson, Winchester, VA is a top 3-star hotel on Expedia for families, and features an indoor pool and free breakfast. Other good options for your kid-friendly vacation include Fairfield Inn & Suites Strasburg Shenandoah Valley and Quality Inn. Attractions like Shenandoah Valley Discovery Museum and Wilson’s Wild Animal Park are also fun for kids of all ages.
What's the best hotel for couples in Winchester?
Smithfield Farm B&B is a favorite 3-star B&B for couples, and features free breakfast and free parking. Other good choices for a stay with your sweetheart include Celebration Retreat and The George Washington Hotel, A Wyndham Grand Hotel.
What are some hotels with pools in Winchester?
TownePlace Suites by Marriott Front Royal is a popular 3-star hotel featuring a seasonal outdoor pool, free buffet breakfast, and free WiFi. Other choices that feature an onsite pool include Hampton Inn Winchester N/Conference Center, VA and Wingate by Wyndham Winchester.
What is the best spa hotel in Winchester?
Charming Farmhouse on 36 Acres in Shenandoah Wine Country is a highly recommended spa hotel with a water park. Kick back and relax in the spa tub. Other popular spa hotels in Winchester include Holiday Inn & Suites Front Royal Blue Ridge Shadows and L’Auberge Provencale.
What's the best hotel for staying near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It’s located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
What's it like to stay in 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. A top sight in the area is Hollywood Casino at Charles Town Races. In Winchester, there are 105 hotels and other accommodations to choose from.
What should I see while I'm in Winchester?
Cultural venues include Winchester Little Theater, Museum of the Shenandoah Valley, and Blue Ridge Arts Council and Gallery. Families come for attractions such as Shenandoah Valley Discovery Museum, Dinosaur Land, and Rocking S Ranch. Notable for its historic sites, landmarks like Bing Crosby Stadium, Patsy Cline Historic House, and Hupp’s Hill Civil War Park are not to be missed.
What's the weather like in Winchester?
The hottest months are usually July and June with an average temp of 71°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 38 inches.

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