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Islesboro Island: Houses, Cottages & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 9
    House #147060
    2
      • 2 BR
      • 1 BA
      • Sleeps 5
      Cottage #178936
      15
        avg/night
        • 3 BR
        • 1 HF BA
        • Sleeps 8
        Barn #412090vb
        Viewed 12 times in the last 48 hours
          • 4 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 8
          Cottage #158754
            Exceptional! 5.0/5
            (6 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 4
            House #107129
            6
            Viewed 18 times in the last 48 hours
              Wonderful! 4.9/5
              (38 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Cottage #289927
              38
              Viewed 11 times in the last 48 hours
                Wonderful! 4.9/5
                (35 reviews)
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 4
                Cottage #576738vb
                35
                Viewed 13 times in the last 48 hours
                  Wonderful! 4.8/5
                  (9 reviews)
                  $93
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 3
                  Cottage #3772903
                  9
                  Viewed 5 times in the last 48 hours
                    $57
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 2
                    Studio #579493vb
                    4
                    Viewed 9 times in the last 48 hours
                      avg/night
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 6
                      Cottage #3968158
                      1
                      Viewed 6 times in the last 48 hours
                        Exceptional! 5.0/5
                        (10 reviews)
                        avg/night
                        • 4 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 10
                        House #4142348
                        10
                        Viewed 12 times in the last 48 hours
                          Exceptional! 5.0/5
                          (8 reviews)
                          avg/night
                          • 6 BR
                          • 2 BA
                          • Sleeps 12
                          Farmhouse #209826vb
                          8
                          Viewed 7 times in the last 48 hours
                            avg/night
                            • 2 BR
                            • 1 BA
                            • 1 HF BA
                            • Sleeps 6
                            House #696594vb
                            2
                            Viewed 8 times in the last 48 hours
                              Excellent! 4.7/5
                              (22 reviews)
                              avg/night
                              • 3 BR
                              • 2 BA
                              • Sleeps 5
                              House #3754964
                              22
                              Viewed 11 times in the last 48 hours
                                Exceptional! 5.0/5
                                (10 reviews)
                                $61
                                avg/night
                                • 1 BR
                                • 1 BA
                                • Sleeps 4
                                Apartment #267979
                                10
                                Viewed 12 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (28 reviews)
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 4
                                  Cottage #303113vb
                                  28
                                  Viewed 16 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (9 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Villa #507900vb
                                    9
                                    Viewed 22 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (12 reviews)
                                      $85
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                      Condo #917063
                                      12
                                      Viewed 11 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (27 reviews)
                                        avg/night
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 8
                                        House #582537vb
                                        27
                                        Viewed 7 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (20 reviews)
                                          $85
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          Cabin #473654vb
                                          20
                                          Viewed 18 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            House #3603315
                                              Wonderful! 4.9/5
                                              (7 reviews)
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              House #802225vb
                                              7
                                              Viewed 11 times in the last 48 hours
                                                Exceptional! 5.0/5
                                                (8 reviews)
                                                avg/night
                                                • 5 BR
                                                • 3 BA
                                                • Sleeps 13
                                                House #4165895
                                                8
                                                Viewed 14 times in the last 48 hours
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  Cottage #954456vb
                                                  Viewed 7 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (22 reviews)
                                                    $86
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    Apartment #165030vb
                                                    22
                                                    Viewed 5 times in the last 48 hours
                                                      • 4 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 9
                                                      Cottage #989530
                                                      28
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        House #496804vb
                                                        2
                                                        Viewed 6 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (28 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 1 BA
                                                          • Sleeps 8
                                                          House #3801876
                                                          28
                                                          Viewed 27 times in the last 48 hours
                                                            avg/night
                                                            • 4 BR
                                                            • 1 BA
                                                            • 1 HF BA
                                                            • Sleeps 7
                                                            House #717037vb
                                                            4
                                                            Viewed 13 times in the last 48 hours
                                                              • 5 BR
                                                              • 5 BA
                                                              • 1 HF BA
                                                              • Sleeps 12
                                                              House #927721vb
                                                              Viewed 15 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (18 reviews)
                                                                $86
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 8
                                                                Cabin #3864196
                                                                18
                                                                Viewed 45 times in the last 48 hours
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 10
                                                                  House #721875vb
                                                                  3
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    House #832554vb
                                                                    4
                                                                    Viewed 7 times in the last 48 hours
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      House #859446vb
                                                                      3
                                                                        Exceptional! 5.0/5
                                                                        (31 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 7
                                                                        House #44879vb
                                                                        31
                                                                          Wonderful! 4.9/5
                                                                          (11 reviews)
                                                                          avg/night
                                                                          • 6 BR
                                                                          • 4 BA
                                                                          • Sleeps 20
                                                                          House #134089
                                                                          11
                                                                          Viewed 14 times in the last 48 hours
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            Townhome #287845vb
                                                                            22
                                                                              Wonderful! 4.9/5
                                                                              (12 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 3 BA
                                                                              • Sleeps 7
                                                                              House #840063vb
                                                                              12
                                                                              Viewed 8 times in the last 48 hours
                                                                                Excellent! 4.7/5
                                                                                (7 reviews)
                                                                                $62
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 3
                                                                                Studio #875902vb
                                                                                7
                                                                                Viewed 32 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (6 reviews)
                                                                                  $68
                                                                                  avg/night
                                                                                  • Studio
                                                                                  • 1 BA
                                                                                  • Sleeps 2
                                                                                  Studio #599202vb
                                                                                  6
                                                                                  Viewed 5 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (16 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    House #329873vb
                                                                                    16
                                                                                    Viewed 7 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (16 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      Townhome #460796vb
                                                                                      16
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        Cottage #560935vb
                                                                                        9
                                                                                          Excellent! 4.5/5
                                                                                          (6 reviews)
                                                                                          $63
                                                                                          avg/night
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 2
                                                                                          Studio #4210882
                                                                                          6
                                                                                          Viewed 22 times in the last 48 hours
                                                                                            Excellent! 4.5/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 5
                                                                                            House #114586
                                                                                            10
                                                                                            Viewed 29 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 3 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 20
                                                                                              House #326138vb
                                                                                              9
                                                                                              Viewed 15 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (17 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 6
                                                                                                Cottage #494758vb
                                                                                                17
                                                                                                Viewed 5 times in the last 48 hours
                                                                                                • 1 - 50 of 300+
                                                                                                 

                                                                                                Recent Islesboro Island Reviews

                                                                                                Exactly like the photos!

                                                                                                5 of 5
                                                                                                Convenient and quaint. The owners were kind and the space very comfortable. We loved the tips for the best sunrise and bites to eat in town. Will definitely be coming back.
                                                                                                • Submitted: Nov 7, 2016
                                                                                                • Stayed: Oct 2016

                                                                                                Well maintained & located property for a stay on Mt. Desert Island

                                                                                                5 of 5
                                                                                                The cottage was just as pictured and our family enjoyed our stay, particularly taking advantage of the views, well equipped kitchen, and laundry facilities. The home felt very secluded, but gave quick access to Southwest Harbor and other key points of the island. Kathryn was very responsive throughout the process and left perfectly detailed directions. We'd recommend to families and would enjoy going back some day!
                                                                                                • Submitted: Nov 1, 2016
                                                                                                • Stayed: Oct 2016

                                                                                                Bayleaf is a slice of heaven!

                                                                                                5 of 5
                                                                                                What a gem Bayleaf! Once you pass through the most amazing long driveway through the woods with the fall colors, it opens up to the quaintest cabin in the woods. The views are breathtaking and the cabin feels like home. Being late in October we spent more time inside than we wanted, but we quickly realized that we were so happy being inside on those rainy cold days. We used the fireplace almost none stop on some days and were supplied with plenty of wood and had all the comforts of home, including an outdoor fire pit. The huge bay windows made for such a picturesque view over the water and my husband would often go down to the water and walk the coastline. The house was well supplied with everything you would need and its proximity is close to a local store so you can stock your kitchen up for the week. It was great coming home after a long day of driving around and exploring, to come home and light a fire, pour a glass of wine, and cook a home cooked meal. I highly suggest the local market that is on Saturday mornings. We found some local cheeses, meats, jams and veggies and we also had a wonderful breakfast that we grabbed from a food truck there along with a coffee. I would describe Brooklin in late October as a sleepy town, but most restaurants are still serving and we found some wonderful meals that were in close driving distance. We often stopped by the Brooklin Inn which is in walking distance to the house, for a nightcap/ burger and to see the wonderful staff (Chip and Tammy especially) which made it such a neat experience. We even had a local lobsterman we met on our first night there, Desmond, who dropped off lobsters to us as a surprise for our wedding anniversary! It’s in a perfect central location and we would drive to Acadia National Park, Deer Isle, Stonington, Castine, Surry, Ellsworth and Blue Hill. The longest drive being about an hour and the prettiest drives we have ever had. If I would do this trip again, I would book it earlier than we did, late September or the first week of October as a lot of things are closed. However, the fall foliage and quietness and laid back feel of this town is what we wanted and the Bayleaf and Brooklin delivered!
                                                                                                • Submitted: Nov 1, 2016
                                                                                                • Stayed: Oct 2016