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Top Trending Hotels in Winchester

The George Washington Hotel, A Wyndham Grand Hotel - Winchester Hotels
Rating: 3.5 Stars

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester - Map
"Great hotel"
Great, comfortable room, friendly and helpful staff
Rebecca from Baltimore
This Winchester, VA hotel is 2 blocks from the Old Town Winchester Walking Mall and within a mile of Museum of Shenandoah …More
Wingate by Wyndham Winchester - Winchester Hotels
Rating: 2.5 Stars

Wingate by Wyndham Winchester

150 Wingate Dr, Winchester - Map
"Best hotel in Winchester"
Have stayed at this hotel twice in the last week....both times were great experiences with both the room and the staff!
kyle from maryland
Aloft Winchester - Winchester Hotels
Rating: 3.0 Stars

Aloft Winchester

1055 Millwood Pike (Rt. 50 East), Winchester - Map
"Modern hotel with great ammenities"
Very modern feel, the rooms are spacious and comfortable. Staff is very accommodating.
Jane from Washington, D.C.
Cool Harbor Motel - Front Royal Hotels
Rating: 2.0 Stars

Cool Harbor Motel

141 West 15th Street, Front Royal - Map
"Convenient location from Skyline Drive."
Met our over night needs. Spacious room very inviting. Will keep this on our list when passing through again.
JoeSeabee from Melbourne, FL
Sleep Inn & Suites - Winchester Hotels
Rating: 2.0 Stars

Sleep Inn & Suites

140 Costello Dr, Winchester - Map
"Very happy, except hallway smelled of smoke"
Good breakfast, nice helpful staff . Rooms were a good size, nice touch with microwave, fridge
A Traveller
Travelodge - Winchester - Winchester Hotels
Rating: 2.0 Stars

Travelodge - Winchester

160 Front Royal Pike, Winchester - Map
Recommend for staying, friendly staff and good rooms, only get a room on the entrance side so the interstate traffic doesn't keep u up
A Traveller
Red Roof Inn Winchester, VA - Winchester Hotels
Rating: 2.0 Stars

Red Roof Inn Winchester, VA

991 Millwood Pike, Winchester - Map
"in the Mountains"
The Hotel is old but very Clean. The people were so nice. I would stay there again if I was in that area.
A Traveller
Located just 2 miles from the Winchester Regional Airport, Red Roof Winchester is just a mile from Shenandoah University and …More
Hotel Strasburg - Strasburg Hotels
Rating: 3.0 Stars

Hotel Strasburg

213 S. Holliday Street, Strasburg - Map
"More of an inn than a hotel."
Strasburg is halfway to my destination. I wanted a place to stop to break up the trip, a place that provided a good night's sleep, a hot shower, and a comforting meal at a reasonable price. I had stopped there on the way south two weeks ago, so this was my second stay. The Strasburg Hotel provided the warmth that the usual cookie-cutter rooms in the chain hotels could not. I save the Hotel on my Garmin so that it will readily available on the next trip. Check out the website. It is as advertised.
George from Delaware County, NY
Country Inn & Suites By Carlson, Winchester, VA - Winchester Hotels
Rating: 2.5 Stars

Country Inn & Suites By Carlson, Winchester, VA

141 Kernstown Commons Blvd, Winchester - Map
"Our one night stay was excellent. Would recommend"
Excellent one night stay on our way home from vacation in Myrtle Beach. It was close to restaurants groceries and gas. The hotel was very clean and the room was just about like home. The breakfast was great and the staff were very friendly. I would very much recommend this hotel to my family and friends. The only thing I would suggest is that the signs to your hotel from hwy 81 were clearer. It was a little confusing. GREAT HOTEL....
A Traveller
Comfort Inn Winchester - Winchester Hotels
Rating: 2.0 Stars

Comfort Inn Winchester

1601 Martinsburg Pike, Winchester - Map
My family and I enjoyed our stay. Clean friendly front desk staff. There is a Denny's connected. And a great pool , but was too cool to enjoy, Breakfast was terrific, Would stay again. Jeff Rice SCPO, USN Retired
Jeff from Houston Pa

Search from 35 Winchester Hotels


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    Winchester Hotel Guide

    Everybody wins when a trip to Winchester is in the mix. Come to this beautiful corner of the Shenandoah Valley to experience vineyards, farms, and historic landmarks. Winchester played a role in the French and Indian War, the Revolutionary War, and the Civil War, and many of the city’s historic landmarks and attractions allow visitors to learn about American history. One such attraction is Winchester’s vast assortment of apples, which grow all over the city.. When you’re ready to sample the city’s delicious apple pies, can help you snag a great rate at a top Winchester hotel without any hassles. Stay right here for exclusive deals that will help you save money and make the most of your trip.

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    Life in the Famous Shenandoah Valley

    Winchester offers the best of country living mixed with all the city conveniences you could dream of. What else would you expect from a city that’s situated between the wilderness and the busy city lifestyle of Washington D.C.? People love to visit Loudoun Street to explore the many boutiques and restaurants in the city’s downtown. The city also possesses more than a dozen recognized historical sites, many of which were built in the 1700s. If you want to stick close to the historical region of the city, you’re in luck; a number of Winchester, Virginia hotels are situated just a stone’s throw away from the cobbled sidewalks and buildings of yesteryear.

    The Weather of Winchester

    Are you ready to experience the magical seasons of the Shenandoah Valley? Winchester experiences sunny summers and cool winters. In fact, the region is considered milder than many other portions of the United States. Summer temperatures often stay between 20 and 31 degrees Celsius, while winter temperatures tend to linger between 3 and 11 degrees Celsius. Fall and spring are particularly delightful times to visit, as the area averages around 20 degrees Celsius in these seasons.

    Wonderful Winchester Activities

    Prepare yourself for an enchanted trip that includes visits to the Museum of the Shenandoah Valley, Stonewall Jackson's Headquarters, and the Shenandoah Valley Discovery Museum. Watch history come to life at the Old Court House Civil War Museum, Stonewall Confederate Cemetery, Kernstown Battlefield, Pritchard House, and Abram's Delight. Winchester also features everything from farm stands to ghost tours. Don’t plan your trip without checking out our exclusive discounts on hotels in Winchester, VA. You’re just seconds away from cheap offers that will save you time and money.

    Book Top Winchester, VA Hotels Today

    Are you looking for a price on a Winchester hotel that won’t make you wince in pain? Do something good for your budget by booking your accommodations using our exclusive bargains. What’s more, you’ll get the guaranteed best deal possible when you combine your hotel and Winchester flight into one great package. Did we mention that many of our packages include rooms at Winchester luxury hotels? Our travel experts are standing by to give you the inside scoop on how to save more money than ever before. Experience the legends and beauty of the famous Shenandoah Valley using travel bargains from Expedia.

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    *For these packages, package savings is at least equal to the cost of the flight or hotel if booked separately. Note: For packages including flights, you will be charged by the airline for the flight, but your savings on the package will equal the cost of the flight.