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Historic Winchester, VA Hotels $55

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Featured Winchester Historic Hotels

See all 216 Hotels in Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester
3.5 out of 5.0
4.7 out of 5 (205 reviews)
Nice hotelThe staff were very accommodating. Our check in wasn't until 4pm but we called to question early check in because we had a wedding to attend at 5pm, which was 30 minutes away. The staff were able to clean our room and have it ready by 12pm. I would recommend this hotel to anyone.
  Jul 18, 2017

$98

$98
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive, Winchester
2.5 out of 5.0
4.5 out of 5 (157 reviews)
Nice hotel. Good food Good location for my needs. Close to convenience store and restaurants.
  Mar 4, 2017

$112

$112
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

300 Marriott Drive, Winchester
3.0 out of 5.0
4.3 out of 5 (89 reviews)
This hotel had a 10 for everything. Would definitely stay there again .
  Jun 29, 2017

$94

$94
Fairfield & Suites by Marriott Winchester

Fairfield & Suites by Marriott Winchester

250 Front Royal Pike, Winchester
2.5 out of 5.0
4.4 out of 5 (30 reviews)
A brief but very comfortable stay!Very friendly staff, even the lady in the breakfast room was so nice, friendly and helpful! She helped me put away my breakfast trash and made conversation with almost everyone eating breakfast!
  Feb 19, 2017

$93

$93
Best Western Lee-jackson Inn & Conference Center

Best Western Lee-jackson Inn & Conference Center

711 Millwood Ave, Winchester
2.5 out of 5.0
3.4 out of 5 (121 reviews)
No problems with having a dog. Easy to find. Easy departure
  Aug 17, 2017

$74

$74
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

991 Millwood Pike, Winchester
2.0 out of 5.0
3.4 out of 5 (179 reviews)
Pleasantly surprised We found this motel was up to date, ideally located, and with very high standards.
  Jul 1, 2017

$62

$62
Cool Harbor Motel

Cool Harbor Motel

141 West 15th Street, Front Royal
2.0 out of 5.0
3.0 out of 5 (3 reviews)
Sparse room, but cleanQuiet room, good A/C (it was really hot/humid out). Sparse furnishings (single bed, no chairs, small table, small fridge). but clean. Old fixtures in bathroom but functional. The wifi was surprisingly excellent/fast considering the age of the motel.
  Jul 7, 2017

$56

$56
L Auberge Provencale Bed and Breakfast

L Auberge Provencale Bed and Breakfast

13630 Lord Fairfax Highway, White Post
3.5 out of 5.0
5.0 out of 5 (4 reviews)
awesome stay!My husband and I celebrated our anniversary here and it was amazing. The staff was great from beginning to end. We enjoyed all the delicious food fro dinner and breakfast. We have decided to make this one of our spots when we need to get away from the kids, city and the everyday hustle.
  Jul 18, 2016
Quality Inn Skyline Dr

Quality Inn Skyline Dr

10 S Commerce Ave, Front Royal
2.5 out of 5.0
3.2 out of 5 (86 reviews)
The best breakfast!!We stayed for a weekend getaway. Loved the balcony over the pool. Our bathroom light shorted out the 2nd day and someone was right up to fix it. Wish the elevator was more centrally located. The breakfast was the best thing about our stay. It was worth getting up early for. Would stay here again ...
  Aug 18, 2017

$80

$80
Hotel Strasburg

Hotel Strasburg

213 S. Holliday Street, Strasburg
3.0 out of 5.0
4.0 out of 5 (144 reviews)
A very artsy hotel with a nice restaurant. We (family of three) stayed just one night and we had there a birthday dinner for my wife that we enjoyed a lot. Our room was upgraded without our request and the suite was very large, clean and artsy. The only problem was TV reception and absence of any TV guide to know what channels to look for ...
  Aug 17, 2017

$79

$79
Wayside Inn

Wayside Inn

7783 Main St, Middletown
3.5 out of 5.0
4.7 out of 5 (18 reviews)
Many VisitsI have stayed here many times in many different rooms. We found 23 a bit wanting in space. Everything had to be on top of the dresser. Closet was strange. No door, quite large. Hangers were down the far end. No light. We nearly forgot the things we had hung up. Dinner was delightful. We always choose ...
  Aug 19, 2017

$105

$105
Travelodge - Winchester

Travelodge - Winchester

160 Front Royal Pike, Winchester
2.0 out of 5.0
3.4 out of 5 (276 reviews)
Reasonable place in WinchesterNice room; close to restaurants and shopping; great pool; staff not so pleasing or engaged. Otherwise, a pleasant stay.
  Aug 17, 2017

$55

$55
Aloft Winchester

Aloft Winchester

1055 Millwood Pike (Rt. 50 East), Winchester
3.0 out of 5.0
4.3 out of 5 (227 reviews)
Excellent location and price, I had really nice experience
  Jul 31, 2017

$84

$84
The Ashby Inn & Restaurant

The Ashby Inn & Restaurant

692 Federal St, Paris
3.5 out of 5.0
4.9 out of 5 (8 reviews)
Romantic Bed and Breakfast. it was perfect for a special occasion.
  Jul 5, 2017

$160

$160
Holiday Inn Express Hotel & Suites Winchester

Holiday Inn Express Hotel & Suites Winchester

142 Foxridge Ln, Winchester
2.5 out of 5.0
4.4 out of 5 (61 reviews)
Nice hotel for 1 night stay. All around good stay. Just too bad room was stuffy and had smell like previous guest smoked in room. Thought it would pass and wear off but persisted through the night. Should have asked to change rooms. Staff at front desk and breakfast very good.
  Jul 11, 2017

$108

$108
Country Inn & Suites By Carlson, Winchester, VA

Country Inn & Suites By Carlson, Winchester, VA

141 Kernstown Commons Blvd, Winchester
3.0 out of 5.0
4.3 out of 5 (220 reviews)
mattressOur stay was good, but would have been better if there was a better mattress on the bed. It was lumpy. I didn't sleep well at all. The ruin was nice and clean. The mattress was really the only complaint I had.
  Aug 17, 2017

$76

$76
Hampton Inn - Winchester N/Convention Center

Hampton Inn - Winchester N/Convention Center

1204 Berryville Avenue, Winchester
2.5 out of 5.0
4.5 out of 5 (28 reviews)
Great ValueThe hotel executed well on everything you expect from this type of hotel at this price. What made are stay was the brunch is a cut above. Good selection and fresh. Could have some more "healthy" items, but all the basics are there
  Aug 17, 2017

$98

$98
Holiday Inn Winchester Se-Historic Gateway

Holiday Inn Winchester Se-Historic Gateway

333 Front Royal Pike, Winchester
3.0 out of 5.0
4.4 out of 5 (100 reviews)
good place to stay while on the roadThe hotel is located just of I81, meets expectations, it was quiet, and a good place to rest for an overnight on the road. Breakfast is extra, menu limited. There's a much better Perkins restaurant nearby. Went to the bar for a drink in the evening. The place was a mess, more of a family rec room ...
  Aug 18, 2017

$93

$93
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

120 Wingate Drive, Winchester
3.0 out of 5.0
4.5 out of 5 (50 reviews)
Convenient locationLocated right across from the Apple Blossom Mal and about a half mile drive to Shenandoah University campus. Lots of restaurants very close or within walking distance.
  Jul 22, 2017

$107

$107
Sleep Inn & Suites

Sleep Inn & Suites

140 Costello Dr, Winchester
2.0 out of 5.0
4.1 out of 5 (71 reviews)
Nice hotel. Staff was nice right from the start! Clean and comfortable. Breakfast is a little lack but serves its purpose.
  Nov 4, 2016
Map

Recently booked Historic Hotels in Winchester

Hampton Inn Front Royal
2.5 out of 5.0
Last booking: 49 minutes ago
Super 8 Winchester VA
2.0 out of 5.0
Last booking: 58 minutes ago
Wingate by Wyndham Winchester
2.5 out of 5.0
Last booking: 1 hour ago
Holiday Inn Winchester Se-Historic Gateway
3.0 out of 5.0
Last booking: 1 hour ago
Hampton Inn Winchester-University/Mall Area
2.5 out of 5.0
Last booking: 1 hour ago
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 out of 5.0
Last booking: 2 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5.0
Last booking: 2 hours ago
Holiday Inn Express Hotel & Suites Winchester
2.5 out of 5.0
Last booking: 4 hours ago
Hotel Strasburg
3.0 out of 5.0
Last booking: 4 hours ago

Historic Winchester Hotels Information

Travel back in time and reserve a room at a historic Winchester hotel.
  • Choose from our vast selection of historic hotels in Winchester
  • Stay in a classic hotel with intriguing antiquity
  • Don’t waste time searching for lower prices elsewhere

Book today and experience the heritage and allure of a hotel with a story and a past. Look past the sparkly, high-rise hotels and go the rustic route instead.

Because when you choose a historic Winchester hotel with a story to tell, you’ll have your own tales to share when you go back home. We doubt those brand new high-rises have that kind of charisma! Older accommodations have a colorful past, and many are located at the site of a significant event. These fascinating relics offer a glimpse into a different era and way of life. During your stay at a historical hotel in Winchester, marvel at the on-site antiques and explore the nearby landmarks. You’ll feel as though you traveled through time as you take a tour of the area and other historical attractions during your vacation.

While we can’t offer you the same hotel rates of yesteryear, we can present you with the lowest prices on the market today. Thanks to our great prices, you can confidentially book classic historic Winchester hotels knowing you won’t find a better discount elsewhere. Whether you’re a history buff wanting to brush up on your facts or a jetsetter looking for a famous place to rest, browse our selection of historic Winchester hotels. Make your reservations today and put the cash you saved toward stocking up on antique souvenirs, artifacts, and artwork.