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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Wonderful! 4.8/5
    (13 reviews)
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 7
    Cottage #342767vb
    13
    Viewed 14 times in the last 48 hours
      Excellent! 4.4/5
      (5 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      House #640850vb
      5
      Viewed 9 times in the last 48 hours
        • 3 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 6
        Farmhouse #459350vb
        15
          • Studio
          • 1 BA
          • Sleeps 2
          Hotel #3905417
          Viewed 6 times in the last 48 hours
            Exceptional! 5.0/5
            (14 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 4
            Cottage #445209vb
            14
            Viewed 44 times in the last 48 hours
              Wonderful! 4.9/5
              (19 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • Sleeps 6
              House #488561vb
              19
              Viewed 24 times in the last 48 hours
                Exceptional! 5.0/5
                (20 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 4
                Cottage #618415vb
                20
                Viewed 12 times in the last 48 hours
                  Wonderful! 4.9/5
                  (33 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Sleeps 12
                  House #3514594
                  33
                  Viewed 28 times in the last 48 hours
                    Wonderful! 4.8/5
                    (12 reviews)
                    avg/night
                    • 4 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                    House #507217vb
                    12
                    Viewed 20 times in the last 48 hours
                      Wonderful! 4.8/5
                      (13 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      Cabin #617797vb
                      13
                      Viewed 66 times in the last 48 hours
                        Wonderful! 4.9/5
                        (10 reviews)
                        avg/night
                        • 4 BR
                        • 4 BA
                        • 1 HF BA
                        • Sleeps 12
                        House #4050256
                        10
                        Viewed 10 times in the last 48 hours
                          Exceptional! 5.0/5
                          (9 reviews)
                          avg/night
                          • 6 BR
                          • 3 BA
                          • Sleeps 10
                          House #4064007
                          9
                          Viewed 16 times in the last 48 hours
                            avg/night
                            • 6 BR
                            • 4 BA
                            • Sleeps 22
                            House #775020vb
                            4
                            Viewed 42 times in the last 48 hours
                              Exceptional! 5.0/5
                              (12 reviews)
                              avg/night
                              • 6 BR
                              • 5 BA
                              • Sleeps 20
                              Estate #4258796
                              12
                              Viewed 73 times in the last 48 hours
                                Excellent! 4.7/5
                                (7 reviews)
                                avg/night
                                • 4 BR
                                • 2 BA
                                • Sleeps 10
                                House #3467511
                                7
                                Viewed 27 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (46 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  Condo #575909vb
                                  46
                                  Viewed 16 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (11 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • Sleeps 8
                                    House #584821vb
                                    11
                                    Viewed 13 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (14 reviews)
                                      avg/night
                                      • 5 BR
                                      • 3 BA
                                      • Sleeps 12
                                      House #622993vb
                                      14
                                      Viewed 10 times in the last 48 hours
                                        Wonderful! 4.8/5
                                        (12 reviews)
                                        avg/night
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 16
                                        House #705717vb
                                        12
                                        Viewed 37 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (8 reviews)
                                          avg/night
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 8
                                          Lodge #728409vb
                                          8
                                          Viewed 5 times in the last 48 hours
                                            avg/night
                                            • 3 BR
                                            • 1 BA
                                            • Sleeps 8
                                            House #4281236
                                            1 Review
                                            Viewed 7 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (71 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Cottage #216065
                                              71
                                              Viewed 56 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (18 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 8
                                                House #236935vb
                                                18
                                                Viewed 8 times in the last 48 hours
                                                  Very Good! 4.2/5
                                                  (53 reviews)
                                                  avg/night
                                                  • 11 BR
                                                  • 7 BA
                                                  • 1 HF BA
                                                  • Sleeps 24
                                                  Estate #366016vb
                                                  53
                                                  Viewed 45 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (43 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    Apartment #393681vb
                                                    43
                                                    Viewed 37 times in the last 48 hours
                                                      Wonderful! 4.9/5
                                                      (31 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      Apartment #3591655
                                                      31
                                                      Viewed 18 times in the last 48 hours
                                                        Wonderful! 4.8/5
                                                        (6 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        House #506003vb
                                                        6
                                                        Viewed 15 times in the last 48 hours
                                                          Excellent! 4.6/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 3
                                                          Apartment #606556vb
                                                          8
                                                          Viewed 10 times in the last 48 hours
                                                            Excellent! 4.5/5
                                                            (10 reviews)
                                                            avg/night
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            Cottage #3939054
                                                            10
                                                            Viewed 7 times in the last 48 hours
                                                              Good! 3.9/5
                                                              (8 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              Chalet #3938844
                                                              8
                                                              Viewed 28 times in the last 48 hours
                                                                • 3 BR
                                                                • 2 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                House #718791vb
                                                                5
                                                                  Exceptional! 5.0/5
                                                                  (8 reviews)
                                                                  avg/night
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                  House #4153058
                                                                  8
                                                                    Wonderful! 4.9/5
                                                                    (7 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 6
                                                                    House #4155013
                                                                    7
                                                                    Viewed 11 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (8 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      House #854910vb
                                                                      8
                                                                      Viewed 7 times in the last 48 hours
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 7
                                                                        Chateau / Country House #4238218
                                                                        8
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 4 BA
                                                                          • Sleeps 11
                                                                          House #955208vb
                                                                          Viewed 11 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (5 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 9
                                                                            House #174313
                                                                            5
                                                                            Viewed 7 times in the last 48 hours
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 3 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 16
                                                                              Barn #3939140
                                                                              4
                                                                              Viewed 5 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (5 reviews)
                                                                                avg/night
                                                                                • 9 BR
                                                                                • 8 BA
                                                                                • Sleeps 16
                                                                                Estate #717669vb
                                                                                5
                                                                                Viewed 12 times in the last 48 hours
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • Sleeps 10
                                                                                  House #3959837
                                                                                  12
                                                                                  Viewed 39 times in the last 48 hours
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 15
                                                                                    House #874852vb
                                                                                    Viewed 17 times in the last 48 hours
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      House #590505vb
                                                                                      2 Reviews
                                                                                      Viewed 11 times in the last 48 hours
                                                                                        Excellent! 4.7/5
                                                                                        (21 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 7
                                                                                        House #588061vb
                                                                                        21
                                                                                        Viewed 5 times in the last 48 hours
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 8
                                                                                          Condo #3815326
                                                                                          Viewed 17 times in the last 48 hours
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            Apartment #630322vb
                                                                                            2 Reviews
                                                                                            Viewed 10 times in the last 48 hours
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 6
                                                                                              Estate #837730vb
                                                                                              1 Review
                                                                                              Viewed 12 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (17 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #300900
                                                                                                17
                                                                                                Viewed 23 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (16 reviews)
                                                                                                  avg/night
                                                                                                  • 9 BR
                                                                                                  • 4 BA
                                                                                                  • Sleeps 20
                                                                                                  House #428459vb
                                                                                                  16
                                                                                                  Viewed 46 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (7 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
                                                                                                    House #585864vb
                                                                                                    7
                                                                                                    Viewed 27 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (29 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      House #3781677
                                                                                                      29
                                                                                                      Viewed 7 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Hillsdale: Houses, Cottages & More (300+)

                                                                                                       

                                                                                                      Recent Hillsdale Reviews

                                                                                                      Lovely, warm, and comfortable Thanksgiving weekend

                                                                                                      4 of 5
                                                                                                      We enjoyed this home very much over Thanksgiving (while our own was under renovation). The 3 bedrooms were just right for 2 couples and 2 teens. While we didn't expect several inches of snow to greet us, it just made for a cozier time by the fire, playing family games, and sipping wine! Beds and linens were comfortable, kitchen was adequately provisioned, and house was very clean. We loved the view of a snowy pond from the hot tub and sauna as well. The only blip on the radar was an apparent malfunction of the wood stove (whose flue is supposed to always be open automatically) on our last night resulting in smoke pouring thru stove door into the room. We had successful fires the other nights, and Lourdes committed to looking into that issue. I'd recommend this lovely home and imagine it's even more welcoming in the summer.
                                                                                                      • Submitted: Nov 26, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Great house for a reunion!

                                                                                                      5 of 5
                                                                                                      Wonderful house for a reunion- slept 6 of us comfortably. Beautiful fireplace and living room. We didn't use the hot tub or fireplace on the deck ( we were there in November and it was windy!) but imagine they would be great in better weather. Lots to do for us middle aged women in Lenox, Lee and Sturbridge!
                                                                                                      • Submitted: Nov 17, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Stylish, well-appointed apartment close to everything.

                                                                                                      5 of 5
                                                                                                      As mentioned previously, apartment is more spacious than appearing in photos. Mark was a great host--easy key pick up and provides necessities for the stay. Apartment was in a perfect location, steps from amazing restaurants and shops. Can't wait to return!
                                                                                                      • Submitted: Nov 15, 2016
                                                                                                      • Stayed: Nov 2016