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Check Prices on Hotels in Massachusetts

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Featured Massachusetts Ski Hotels

See all 6,615 Properties in Massachusetts

Estimated price for 1 night/2 adults

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock, MA
    3.0 out of 5.0
     
     
    4.2 out of 5 (969 reviews)

    Located near the slopes, this Hancock condo building is within 6 mi (10 km) of Pittsfield State Forest and Mount Greylock State Reservation Visitor Center and ...

    Loved it, we will be back many times over. This is a fantastic place to stay.
    Oct 11, 2019

    $105 per night for 2 guests

    Oct 20 - Oct 21
    Vacation Village in the Berkshires$105
    Premium Property & Amenities. Ski Season is Filling up Quickly, Don't Miss Out!

    Premium Property & Amenities. Ski Season is Filling up Quickly, Don't Miss Out!

    Hancock, MA
       
       
      4.9 out of 5 (27 reviews)

      Set amidst the mountains, this ski-in/ski-out condo building in Hancock is within 9 mi (15 km) of Pittsfield State Forest and Mount Greylock State Reservation ...

      Long summer weekendThe condo was clean, large, and inviting. All of the amenities you could ask for were provided. Our kids loved it and the accessibility was great. The only "complaint" were the pools were a bit lack luster but that isn't the condo's fault . Great escape
      Aug 15, 2019

      Premium Property & Amenities. Ski Season is Filling up Quickly, Don't Miss Out!Get Rates

      Yankee Inn

      Yankee Inn

      461 Pittsfield Rd, Lenox, MA
        2.5 out of 5.0
         
         
        4.1 out of 5 (735 reviews)

        Conveniently near skiing facilities, this Lenox hotel is located in the city center within 3 mi (5 km) of Kennedy Park, Bousquet Ski Area, and Pleasant Valley ...

        Rooms were spacious and beds were extremely comfortable. Staff at desk were very informative with directions and places for eating.
        Oct 11, 2019

        $80 per night for 2 guests

        Nov 10 - Nov 11
        Yankee Inn$80
        Berkshire Valley Inn

        Berkshire Valley Inn

        2541 Hancock Rd, Williamstown, MA
          2.5 out of 5.0
           
           
          4.4 out of 5 (266 reviews)

          Located near the slopes, this Williamstown hotel is in the mountains, within 9 mi (15 km) of Waubeeka Golf Links and Mount Greylock State Reservation Visitor ...

          My home away from home. Nestled on the western side of Mount Greylock, this is my favorite place to stay. Quiet and restorative. Impeccably clean.
          Sep 28, 2019

          $99 per night for 2 guests

          Oct 20 - Oct 21
          Berkshire Valley Inn$99
          Jiminy Peak Mountain Resort

          Jiminy Peak Mountain Resort

          37 Corey Rd, Hancock, MA
            3.0 out of 5.0
             
             
            4.0 out of 5 (610 reviews)

            Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.7 km) from Mount Greylock State Reservation Visitor Center and ...

            The staff at check in were more concerned with talking with each other than checking me in. After they talked a few minutes about room 40 needing a new key I needed to interrupt. It was 3 pm and I was rushing to make it to a 4 on wedding. The directions were awful and overall not a good ...
            Sep 29, 2019

            $115 per night for 2 guests

            Nov 11 - Nov 12
            Jiminy Peak Mountain Resort$115
            Hampton Inn & Suites Berkshires Lenox

            Hampton Inn & Suites Berkshires Lenox

            445 Pittsfield Rd, Lenox, MA
              2.5 out of 5.0
               
               
              4.6 out of 5 (519 reviews)

              Conveniently located near the ski slopes, this Lenox hotel is within 2 mi (3 km) of Arrowhead Museum, Bousquet Ski Area, and Kennedy Park. Pleasant Valley Wilderness ...

              Set back from road but a convenient location. Friendly and helpful staff. Good variety for breakfast and spacious hotel. A good base from which to explore the Berkshires.
              Oct 1, 2019

              $96 per night for 2 guests

              Oct 29 - Oct 30
              Hampton Inn & Suites Berkshires Lenox$96
              Westford Regency Inn & Conference Center

              Westford Regency Inn & Conference Center

              219 Littleton Rd, Westford, MA
                3.0 out of 5.0
                 
                 
                4.0 out of 5 (762 reviews)

                Conveniently near skiing facilities, this Westford hotel is located in a shopping district, within 3 mi (5 km) of Westford Museum and Historical Society and ...

                I liked the open lobby area which had a lot of information on activities going on.
                Sep 18, 2019

                $101 per night for 2 guests

                Nov 10 - Nov 11
                Westford Regency Inn & Conference Center$101
                Doubletree by Hilton Hotel Leominster

                Doubletree by Hilton Hotel Leominster

                99 Erdman Way, Leominster, MA
                  3.5 out of 5.0
                   
                   
                  4.2 out of 5 (681 reviews)

                  Conveniently located near the ski slopes, this Leominster hotel is 2.3 mi (3.7 km) from The Mall at Whitney Field and within 6 mi (10 km) of Fitchburg State ...

                  Great stay! You did keep it a little cold inside.
                  Oct 5, 2019

                  $122 per night for 2 guests

                  Nov 10 - Nov 11
                  Doubletree by Hilton Hotel Leominster$122
                  Monument Mountain Motel

                  Monument Mountain Motel

                  247 Stockbridge Rd, Great Barrington, MA
                    2.5 out of 5.0
                     
                     
                    4.4 out of 5 (170 reviews)

                    Situated in Great Barrington, this ski motel is within 3 mi (5 km) of Lake Mansfield Park, Mahaiwe Performing Arts Center, and Beartown State Forest. Ski Butternut ...

                    The room was really clean and cute. I wasn't sure what to expect going in, but it was nice!
                    Oct 12, 2019

                    $70 per night for 2 guests

                    Oct 17 - Oct 18
                    Monument Mountain Motel$70
                    Shaker Mill Inn

                    Shaker Mill Inn

                    7 Albany Road, West Stockbridge, MA
                      2.5 out of 5.0
                       
                       
                      4.7 out of 5 (204 reviews)

                      Conveniently located near the ski slopes, this West Stockbridge bed & breakfast is within 6 mi (10 km) of Berkshire Botanical Garden, Beartown State Forest, ...

                      Rarely you get more for your money. This was it. Fantastic accommodations. Wonderful Inn keepers. Great location. We will definitely return and spent a longer time at Shaker Mill Inn. W.J.B.
                      Oct 5, 2019

                      $145 per night for 2 guests

                      Oct 21 - Oct 22
                      Shaker Mill Inn$145
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                      Pocket Guide: Ski Hotels in Massachusetts

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