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Featured Winchester Historic Hotels

See all 248 Hotels in Winchester
Wayside Inn

Wayside Inn

7783 Main St, Middletown
    3.5 out of 5.0
     
     
    4.7 out of 5 (109 reviews)
    Warm welcome / great service. Great atmosphere, great service and friendly staff.
    Apr 14, 2018

    Wayside Inn$95

    Wayside Inn$95
    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
       
       
      4.6 out of 5 (776 reviews)
      Great staff. Rooms large and very comfortable. Would highly recommend.
      Apr 5, 2018

      The George Washington Hotel, A Wyndham Grand Hotel$98

      The George Washington Hotel, A Wyndham Grand Hotel$98
      Hotel Strasburg

      Hotel Strasburg

      213 S. Holliday Street, Strasburg
        3.0 out of 5.0
         
         
        3.9 out of 5 (561 reviews)
        very nice stayThe staff :: B and Lance and several others are what make this place a fantastic place to stay
        Apr 8, 2018

        Hotel Strasburg$79

        Hotel Strasburg$79
        Fairfield & Suites by Marriott Winchester

        Fairfield & Suites by Marriott Winchester

        250 Front Royal Pike, Winchester
          2.5 out of 5.0
           
           
          4.2 out of 5 (142 reviews)
          Easy Access to I-81 and WinchesterThe staff was wonderful. A lovely breakfast is included with your stay. Overall, very nice place to stay.
          Apr 8, 2018

          Fairfield & Suites by Marriott Winchester$93

          Fairfield & Suites by Marriott Winchester$93
          Beautiful Shenandoah Valley Guest Cottage On Working Homestead

          Beautiful Shenandoah Valley Guest Cottage On Working Homestead

          , Winchester
             
             
            5.0 out of 5 (28 reviews)
            Red Roof Inn Winchester, VA

            Red Roof Inn Winchester, VA

            991 Millwood Pike, Winchester
              2.0 out of 5.0
               
               
              3.5 out of 5 (876 reviews)
              Quick on and off for 81Nice place clran enough. The office is great. Staff is very eager to help. Staff cannot control the guess that they get period normally nice and quiet however I stay on Friday the 6th to Saturday the 7th of April was marked by unusually rambunctious guests and I don't know if there was a problem ...
              Apr 7, 2018

              Red Roof Inn Winchester, VA$52

              Red Roof Inn Winchester, VA$52
              Hampton Inn - Winchester N/Convention Center

              Hampton Inn - Winchester N/Convention Center

              1204 Berryville Avenue, Winchester
                2.5 out of 5.0
                 
                 
                4.4 out of 5 (185 reviews)
                We have stayed here a few times. Easey to find and a gas station next door. Plus a mini mart and a Subway shop.
                Mar 12, 2018

                Hampton Inn - Winchester N/Convention Center$98

                Hampton Inn - Winchester N/Convention Center$98
                Motel 6 Front Royal, VA

                Motel 6 Front Royal, VA

                141 West 15th Street, Front Royal
                  2.0 out of 5.0
                   
                   
                  3.3 out of 5 (44 reviews)
                  Clean room. No chaiThe room was clean, the bed was good, but the sheets were a bit scratchy. There was a table but no chair to sit in.
                  Mar 6, 2018

                  Motel 6 Front Royal, VA$50

                  Motel 6 Front Royal, VA$50
                  Freedman's Cottage at Green Hill

                  Freedman's Cottage at Green Hill

                  1732 Millwood Rd, Boyce
                     
                     
                    5.0 out of 5 (1 reviews)
                    The Ashby Inn & Restaurant

                    The Ashby Inn & Restaurant

                    692 Federal St, Paris
                      3.5 out of 5.0
                       
                       
                      4.8 out of 5 (26 reviews)
                      Lovely, peaceful location for a get-awayHad a wonderful three days at the Ashby Inn! Beautiful room with a view of farm lands, really appreciated the fireplace and the glass of port that I enjoyed by the fire after dinner. Elegant bathroom, comfy bed. Breakfast was INCREDIBLE ! (Delicious, organic and local. Didn't need lunch!) Staff could ...
                      Apr 3, 2018

                      The Ashby Inn & Restaurant$160

                      The Ashby Inn & Restaurant$160
                      Clarion Inn & Conference Center

                      Clarion Inn & Conference Center

                      711 Millwood Ave, Winchester
                        2.5 out of 5.0
                         
                         
                        3.7 out of 5 (640 reviews)
                        Convenient hotel, 5 minutes off #81Efficient check in. Room 107 is on first floor , close to our car. Two doubles beds were comfortable and clean. Small bathroom was clean , with shampoo, conditioner, and soap. Three big clean towels were provided. We did not make use of the coffee maker or the iron and ironing board. Because we had ...
                        Apr 1, 2018

                        Clarion Inn & Conference Center$72

                        Clarion Inn & Conference Center$72
                        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 (689 reviews)
                          Pit stop...Stopped while heading back from spring break. Nice hotel...big ... clean. Good location. GREAT breakfast buffet !!! YuMmYyy !!!
                          Apr 9, 2018

                          Hampton Inn Winchester-University/Mall Area$129

                          Hampton Inn Winchester-University/Mall Area$129
                          Motel 6 Winchester, VA

                          Motel 6 Winchester, VA

                          2951 Valley Avenue, Winchester
                            2.0 out of 5.0
                             
                             
                            3.9 out of 5 (377 reviews)
                            Nice, renovated hotel on a main roadThe staff were amazing. The hotel is very clean and taken care of. I was impressed with the size of the rooms. I travel to this area for work and will definitely he using this place for the remainder of my contract!
                            Apr 3, 2018

                            Motel 6 Winchester, VA$57

                            Motel 6 Winchester, VA$57
                            Wingate by Wyndham Winchester

                            Wingate by Wyndham Winchester

                            150 Wingate Dr, Winchester
                              2.5 out of 5.0
                               
                               
                              4.4 out of 5 (760 reviews)
                              Frenidly cleanVery impressive staff!! Becky at the front desk is a exceptional employee. I had problems with my truck the morning we were leaving so she put us back in our room so my wife could stay while I fixed the problem and directed me to a mechanic. It all worked out thanks to her.
                              Apr 12, 2018

                              Wingate by Wyndham Winchester$84

                              Wingate by Wyndham Winchester$84
                              Comfort Inn Winchester

                              Comfort Inn Winchester

                              1601 Martinsburg Pike, Winchester
                                2.5 out of 5.0
                                 
                                 
                                4.3 out of 5 (336 reviews)
                                Excellent area to walk my little dogs all around the building
                                Apr 17, 2018

                                Comfort Inn Winchester$79

                                Comfort Inn Winchester$79
                                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 (288 reviews)
                                  Great place Loved it, only down fall was our room was set on heat and it was 75 degrees outside. Took a few hours for the room to cool down. Other than that, great experience all around.
                                  Apr 15, 2018

                                  Holiday Inn Express Hotel & Suites Winchester$104

                                  Holiday Inn Express Hotel & Suites Winchester$104
                                  Holiday Inn Winchester Se-Historic Gateway

                                  Holiday Inn Winchester Se-Historic Gateway

                                  333 Front Royal Pike, Winchester
                                    3.0 out of 5.0
                                     
                                     
                                    4.5 out of 5 (519 reviews)
                                    An excellent experiencefor what is generally less than a 4 or 5 star hotel, this one was excellent
                                    Apr 19, 2018

                                    Holiday Inn Winchester Se-Historic Gateway$93

                                    Holiday Inn Winchester Se-Historic Gateway$93
                                    Country Inn & Suites by Radisson, Winchester, VA

                                    Country Inn & Suites by Radisson, Winchester, VA

                                    141 Kernstown Commons Blvd, Winchester
                                      3.0 out of 5.0
                                       
                                       
                                      4.5 out of 5 (1,139 reviews)
                                      large room, comfortable bed & convenient location.
                                      Apr 19, 2018

                                      Country Inn & Suites by Radisson, Winchester, VA$71

                                      Country Inn & Suites by Radisson, Winchester, VA$71
                                      Fairfield Inn & Suites Strasburg Shenandoah Valley

                                      Fairfield Inn & Suites Strasburg Shenandoah Valley

                                      33760 Old Valley Pike, Strasburg
                                        2.5 out of 5.0
                                         
                                         
                                        4.4 out of 5 (506 reviews)
                                        Strasburg visitGood stay comfortable and clean. Would come back again to stay
                                        Mar 28, 2018

                                        Fairfield Inn & Suites Strasburg Shenandoah Valley$84

                                        Fairfield Inn & Suites Strasburg Shenandoah Valley$84
                                        Quality Inn Skyline Dr

                                        Quality Inn Skyline Dr

                                        10 S Commerce Ave, Front Royal
                                          2.5 out of 5.0
                                           
                                           
                                          3.3 out of 5 (397 reviews)
                                          Quiet stayStayed here overnight in way to Williamsburg. Was close to some of the area attractions. Hotel staff was very pleasant and accomodating. Room was clean. Breakfast was offered and was good.
                                          Aug 28, 2017
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                                          About Historic Hotels

                                          Visiting new cities can be more than just highlighting a place on your map, it can also be about experiencing the culture and history of a region. One of the best ways to get a feel for the city's culture is to learn about its past. Touring the region's museums or landmarks is a good kick-off, but staying in a historic hotel can ferry you back to another time period. Pack your luggage (no need for a time machine) as your landmark hotel awaits.

                                          If These Walls Could Talk

                                          Many of the historic accommodations give you a feel for a past period right from the start. With unique architectures and addresses in the heart of the city, it will become obvious what makes Winchester a must for travelers. Fortunately, you aren't required to live like the hotel's past guest. While these accommodations are older, they have most modern comforts to help you relax or keep in touch on your holiday. You will notice rooms furnished with a comfy bed and just about everything you'll want for a wonderful getaway.

                                          Once you have spent time admiring the hotel property, you can check out the well-known landmarks and museums to absorb more of the 's culture. Undoubtedly, all this hopping through history will stimulate your appetite. Be sure to check through the comments section and review the places other travelers to believe is worth visiting. You can also ask your hotel's front desk so you can find out where the best places to enjoy a drink or a meal in are.

                                          Reserve Your Historic Hotel

                                          If you are looking to get the most from your visit, a stay in one of these vintage hotels will elevate your experience in this historically-rich city. Having of these one-of-a-kind hotels to select from. Rates on these historic hotels range from to . You're sure to find at a great rate. However, just like the past eras you're exploring, these rates won't last indefinitely. Book soon to get a place in one of these landmark properties.