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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 9
    House #147060
    2 Reviews
      • 2 BR
      • 1 BA
      • Sleeps 5
      Cottage #178936
      15
        avg/night
        • 3 BR
        • 1 HF BA
        • Sleeps 8
        Barn #412090vb
        Viewed 13 times in the last 48 hours
          • 4 BR
          • 1 BA
          • 1 HF BA
          • Sleeps 8
          Cottage #158754
            Excellent! 4.7/5
            (22 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 5
            House #3754964
            22
            Viewed 9 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 9 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 23 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 13 times in the last 48 hours
                      Exceptional! 5.0/5
                      (27 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 8
                      House #582537vb
                      27
                      Viewed 9 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 20 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 6 times in the last 48 hours
                              Exceptional! 5.0/5
                              (8 reviews)
                              avg/night
                              • 5 BR
                              • 3 BA
                              • Sleeps 13
                              House #4165895
                              8
                              Viewed 23 times in the last 48 hours
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                Cottage #954456vb
                                Viewed 9 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (22 reviews)
                                  $86
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  Apartment #165030vb
                                  22
                                    Wonderful! 4.9/5
                                    (28 reviews)
                                    avg/night
                                    • 4 BR
                                    • 3 BA
                                    • 1 HF BA
                                    • Sleeps 9
                                    Cottage #989530
                                    28
                                    Viewed 14 times in the last 48 hours
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 8
                                      House #496804vb
                                      2 Reviews
                                      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 26 times in the last 48 hours
                                          avg/night
                                          • 4 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 7
                                          House #717037vb
                                          4
                                          Viewed 12 times in the last 48 hours
                                            • 5 BR
                                            • 5 BA
                                            • 1 HF BA
                                            • Sleeps 12
                                            House #927721vb
                                            Viewed 17 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 43 times in the last 48 hours
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 10
                                                House #721875vb
                                                3
                                                Viewed 6 times in the last 48 hours
                                                  avg/night
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 8
                                                  House #832554vb
                                                  4
                                                  Viewed 8 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
                                                      Viewed 5 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (11 reviews)
                                                        avg/night
                                                        • 6 BR
                                                        • 4 BA
                                                        • Sleeps 20
                                                        House #134089
                                                        11
                                                        Viewed 21 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (22 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Townhome #287845vb
                                                          22
                                                          Viewed 14 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (12 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 3 BA
                                                            • Sleeps 7
                                                            House #840063vb
                                                            12
                                                              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
                                                                • Studio
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Studio #599202vb
                                                                6
                                                                  Exceptional! 5.0/5
                                                                  (8 reviews)
                                                                  avg/night
                                                                  • 6 BR
                                                                  • 2 BA
                                                                  • Sleeps 12
                                                                  Farmhouse #209826vb
                                                                  8
                                                                  Viewed 15 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 23 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 22 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 23 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (17 reviews)
                                                                                avg/night
                                                                                • 4 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Cottage #494758vb
                                                                                17
                                                                                Viewed 6 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 4 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 12
                                                                                  House #3791746
                                                                                  6
                                                                                  Viewed 26 times in the last 48 hours
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 4
                                                                                    House #678066vb
                                                                                    3
                                                                                    Viewed 6 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (8 reviews)
                                                                                      avg/night
                                                                                      • 1 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Cabin #205979
                                                                                      8
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Cottage #867479vb
                                                                                        4
                                                                                          Wonderful! 4.9/5
                                                                                          (11 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Cabin #850035vb
                                                                                          11
                                                                                          Viewed 13 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (15 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 5
                                                                                            Farmhouse #396310vb
                                                                                            15
                                                                                            Viewed 11 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 6 BR
                                                                                              • 6 BA
                                                                                              • Sleeps 16
                                                                                              Cottage #4306829
                                                                                              Viewed 8 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 10
                                                                                                House #507910vb
                                                                                                8
                                                                                                Viewed 39 times in the last 48 hours
                                                                                                • 1 - 50 of 300+

                                                                                                Islesboro Island: Houses, Cottages & More (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

                                                                                                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

                                                                                                Peaceful, charming old house by the side of the road

                                                                                                5 of 5
                                                                                                Nicely updated old house, south of Southwest Harbor. Pretty walking path to Manset Shore begins across the street. Kitchen is well-stocked with dishes, pots & pans, utensils, lots of small kitchen appliances (3 types of coffee makers!). Quiet location, even though on road. Good internet connection; nice washer & dryer. Didn't need to fire up the pellet stove in the living room, but it looked inviting. Short drive to Bass Harbor Head lighthouse. Only a few cons - one bathroom, so you need to plan out your showers; no restaurants or shops within walking distance (but easy drive into Southwest Harbor). Very reasonable price for a whole house - would stay again.
                                                                                                • Submitted: Oct 25, 2016
                                                                                                • Stayed: Oct 2016