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Featured The Berkshires Luxury Hotels

See all 144 Properties in The Berkshires
1862 Seasons on Main Bed and Breakfast

1862 Seasons on Main Bed and Breakfast

47 Main Street, Stockbridge
    4.5 out of 5.0
     
     
    5.0 out of 5 (19 reviews)
    The best B & B we have ever stayed in!We have done B&B's for many years, but this experience beats them all. From the communication ahead of time by the lovely innkeeper Amanda, every detail was tended to. Small things like reading glasses in the dining room, umbrellas for loan at every door, use of the kitchen including silverware, ...
    Aug 21, 2017
    Stockbridge Country Inn

    Stockbridge Country Inn

    26 Glendale Road, Stockbridge
      4.5 out of 5.0
       
       
      4.6 out of 5 (41 reviews)
      Weekend Getaway Stayed at the inn for three days. The room was charming and very comfortable. Our hosts were friendly and welcoming. The place was clean and cheerful. Enjoyed our breakfast each day which was generous, varied with delicious selections. Conveniently located to Stockbridge and surrounding points of ...
      Jun 7, 2018

      Stockbridge Country Inn$209

      Stockbridge Country Inn$209
      The Orchards Hotel

      The Orchards Hotel

      222 Adams Rd, Williamstown
      • Free Cancellation
      • Reserve now, pay when you stay
      3.5 out of 5.0
       
       
      4.4 out of 5 (304 reviews)
      classic hotel with touches of agingGood rooms. We loved our spacious 500 sq foot room. Cost just a little more than a regular room. Four poster bed was cool but quite high. Mattress was decent but some lateral movement. One overhead reading light did not work. Burn mark on wall from other light. Room was clean. I loved natural woodwork ...
      Mar 27, 2018

      The Orchards Hotel$179

      The Orchards Hotel$179
      Federal House Inn

      Federal House Inn

      1560 Pleasant Street, South Lee
        3.5 out of 5.0
         
         
        4.8 out of 5 (131 reviews)
        Great hosts and a wonderful breakfastThe grounds and decore were enchanting. The room was clean and very comfortable. The bathroom was updated beautifully with nice amenities. Refreshments were always easily available. The hosts were extremely hospitable and gracious. The breakfast was astounding and extremely delicious.
        Jun 18, 2018

        Federal House Inn$189

        Federal House Inn$189
        Lantern House Motel

        Lantern House Motel

        256 Stockbridge Road, Great Barrington
          2.5 out of 5.0
           
           
          4.1 out of 5 (172 reviews)
          Happy with my stay Clean basic low cost good location I would stay there again
          Jun 8, 2018

          Lantern House Motel$65

          Lantern House Motel$65
          Wagon Wheel Inn

          Wagon Wheel Inn

          484 Pittsfield Rd, Lenox
            2.0 out of 5.0
             
             
            3.6 out of 5 (222 reviews)
            A quiet, little bargain gemWhile there's nothing in particular about the exterior that would suggest that it's anything more than just another older, low-budget motor hotel, my room, though small, was very comfortable, well-maintained, clean, nicely furnished and quiet. And the staff was very friendly and helpful. I found ...
            May 17, 2018

            Wagon Wheel Inn$53

            Wagon Wheel Inn$53
            Hotel On North

            Hotel On North

            297 North Street, Pittsfield
              3.5 out of 5.0
               
               
              4.8 out of 5 (157 reviews)
              Charming, Comfortable, and Professionally-RunI stayed for just two nights to see a show, but it would have been a great place to stay for longer. My room was very large and light, with easy chairs and some antique furniture, and there was a nice lounge in the lobby to sit in. Check-in was somehow possible without the employee needing to spend ...
              Jun 20, 2018

              Hotel On North$149

              Hotel On North$149
              1896 House Country Inn

              1896 House Country Inn

              910 Cold Spring Road, Williamstown
                2.5 out of 5.0
                 
                 
                3.5 out of 5 (31 reviews)
                Fantastic Breakfast Fantastic Breakfast Delicious fresh fruits, muffins etc
                Apr 28, 2018

                1896 House Country Inn$106

                1896 House Country Inn$106
                Yankee Inn

                Yankee Inn

                461 Pittsfield Rd, Lenox
                  2.5 out of 5.0
                   
                   
                  3.9 out of 5 (528 reviews)
                  Nice place. Convenient location.Very nice staff. Clean room with good beds and nicely upgraded bathroom. Good breakfast with made to order omelets. Only drawback to my 1st floor room was very loud upstairs guests. Floor/ceiling does not insulate sound well.
                  Jun 4, 2018

                  Yankee Inn$92

                  Yankee Inn$92
                  Sunset Inn

                  Sunset Inn

                  150 Housatonic Street, Lee
                    1.5 out of 5.0
                     
                     
                    3.1 out of 5 (151 reviews)
                    Convenient and welcomingThe rooms was clean and well kept. I was I bit disappointed to find no guide for the tv or for the surrounding town. The only other thing I missed was coffee in the room. The folks who run(own) the motel were friendly!
                    Jun 18, 2018

                    Sunset Inn$75

                    Sunset Inn$75
                    Maple Terrace Motel

                    Maple Terrace Motel

                    555 Main St., Williamstown
                      2.5 out of 5.0
                       
                       
                      4.6 out of 5 (67 reviews)
                      Nice motel, friendly ownerI stayed there for 2 nights. The room was clean & comfortable.
                      May 14, 2018

                      Maple Terrace Motel$99

                      Maple Terrace Motel$99
                      Howard Johnson by Wyndham Lenox

                      Howard Johnson by Wyndham Lenox

                      462 Pittsfield Rd, Lenox
                        2.0 out of 5.0
                         
                         
                        3.5 out of 5 (583 reviews)
                        Clean big room. Good bfast. Good locationRecommend this hotel. Did not have one complaint. Bonus is lots of cable channels
                        Jun 12, 2018

                        Howard Johnson by Wyndham Lenox$69

                        Howard Johnson by Wyndham Lenox$69
                        Travelodge by Wyndham Great Barrington Berkshires

                        Travelodge by Wyndham Great Barrington Berkshires

                        400 Stockbridge Rd, Great Barrington
                        • Free Cancellation
                        • Reserve now, pay when you stay
                        2.0 out of 5.0
                         
                         
                        3.2 out of 5 (309 reviews)
                        Wonderful place! Excellent bargain, clean rooms, free continental breakfast, and an exceptionally warm, gracious and accommodating extended family running the place. Originally planned to stay for just one night but extended for three additional days.
                        Mar 13, 2018

                        Travelodge by Wyndham Great Barrington Berkshires$75

                        Travelodge by Wyndham Great Barrington Berkshires$75
                        Econo Lodge Lee - Great Barrington

                        Econo Lodge Lee - Great Barrington

                        980 Pleasant Street, Lee
                        • Free Cancellation
                        • Reserve now, pay when you stay
                        2.0 out of 5.0
                         
                         
                        3.2 out of 5 (179 reviews)
                        Nice hotel close to the shrineShort distance to our destination was the main consideration in choosing the hotel . My only concern is the towels were not good.
                        Mar 13, 2018

                        Econo Lodge Lee - Great Barrington$71

                        Econo Lodge Lee - Great Barrington$71
                        Chambery Inn

                        Chambery Inn

                        199 Main St, Lee
                          3.0 out of 5.0
                           
                           
                          4.7 out of 5 (154 reviews)
                          Lovely but ....We have stayed at the Chamberay Inn many times and enjoy our stay very much. We have stayed in many of their various rooms. This stay, however, the room was an awkward design. You couldn’t really watch the TV for the bed and he two chairs were too far away from the TV to watch comfortably. The set ...
                          Feb 17, 2018

                          Chambery Inn$120

                          Chambery Inn$120
                          Black Swan Inn, an Ascend Collection Hotel

                          Black Swan Inn, an Ascend Collection Hotel

                          435 Laurel St, Lee
                            3.0 out of 5.0
                             
                             
                            4.1 out of 5 (408 reviews)
                            Nice, cozy hotel on the waterfront Nice cozy hotel on with option to select rooms with spacious patios overlooking the lake. Unfortunately despite hotel stating that it includes breakfast, breakfast selection is lacking is next to nothing. It consists of some bagels, bread, and yogurt, maybe some cereal but that is all. A nice breakfast ...
                            Jun 2, 2018

                            Black Swan Inn, an Ascend Collection Hotel$104

                            Black Swan Inn, an Ascend Collection Hotel$104
                            Super 8 by Wyndham Lee/Berkshires/Outlet Area

                            Super 8 by Wyndham Lee/Berkshires/Outlet Area

                            170 Housatonic Street, Lee
                            • Free Cancellation
                            • Reserve now, pay when you stay
                            2.0 out of 5.0
                             
                             
                            3.6 out of 5 (293 reviews)
                            Great location, perfect for our tripNice clean room, friendly check in staff. Walking distance to shops and restaurants in Lee.
                            Jun 19, 2018

                            Super 8 by Wyndham Lee/Berkshires/Outlet Area$76

                            Super 8 by Wyndham Lee/Berkshires/Outlet Area$76
                            Lenox Inn

                            Lenox Inn

                            525 Pittsfield Rd, Lenox
                              2.0 out of 5.0
                               
                               
                              3.4 out of 5 (425 reviews)
                              IMHO Was in town for a night and needed a place to sleep. Room was clean , bed was comfortable , shower was fine , towels were clean . Outside looked dated but room fine .
                              Apr 26, 2018

                              Lenox Inn$42

                              Lenox Inn$42
                              Monument Mountain Motel

                              Monument Mountain Motel

                              247 Stockbridge Rd, Great Barrington
                                2.5 out of 5.0
                                 
                                 
                                4.4 out of 5 (94 reviews)
                                Surprisingly nice motel with convenient locationSmall and inexpensive, but clean and more comfortable than expected. Only real complaint is tiny toilet area (elbows touched walls on both sides), but they made the best of the space they had.
                                Jun 22, 2018

                                Monument Mountain Motel$70

                                Monument Mountain Motel$70
                                Crowne Plaza Pittsfield-Berkshires

                                Crowne Plaza Pittsfield-Berkshires

                                1 West St, Pittsfield
                                • Free Cancellation
                                • Reserve now, pay when you stay
                                3.5 out of 5.0
                                 
                                 
                                3.6 out of 5 (501 reviews)
                                Great location, great indoor poolThis hotel is in a great location in the heart of Pittsfield with views of the Berkshires. It is currently being refurbished and we stayed in a basic room that was a little dated but clean and comfortable. The staff was friendly and the indoor pool area is really nice and connected to the restaurant. ...
                                Apr 25, 2018

                                Crowne Plaza Pittsfield-Berkshires$91

                                Crowne Plaza Pittsfield-Berkshires$91
                                Map

                                Recently booked Luxury Hotels in The Berkshires

                                The Porches Inn
                                3.5 out of 5.0
                                Last booking: 31 hours ago
                                Howard Johnson by Wyndham Lenox
                                2.0 out of 5.0
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                                The Villager Motel
                                2.0 out of 5.0
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                                Crowne Plaza Pittsfield-Berkshires
                                3.5 out of 5.0
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                                Best Western Plus Berkshire Hills Inn & Suites
                                2.5 out of 5.0
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                                Holiday Inn Berkshires
                                3.0 out of 5.0
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                                Wyndham Bentley Brook
                                3.0 out of 5.0
                                Last booking: 40 hours ago
                                Days Inn by Wyndham Lenox MA
                                2.0 out of 5.0
                                Last booking: 42 hours ago
                                Yankee Inn
                                2.5 out of 5.0
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                                Luxury The Berkshires Hotels

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