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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 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
            (9 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 6
            Cottage #710780vb
            9
            Viewed 10 times in the last 48 hours
              Exceptional! 5.0/5
              (9 reviews)
              avg/night
              • 1 BR
              • 1 BA
              • Sleeps 4
              Cottage #790510vb
              9
              Viewed 10 times in the last 48 hours
                Exceptional! 5.0/5
                (55 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 4
                Cottage #446948vb
                55
                Viewed 18 times in the last 48 hours
                  Exceptional! 5.0/5
                  (8 reviews)
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 4
                  Cottage #790508vb
                  8
                  Viewed 5 times in the last 48 hours
                    Exceptional! 5.0/5
                    (20 reviews)
                    avg/night
                    • 4 BR
                    • 3 BA
                    • Sleeps 10
                    House #3830794
                    20
                    Viewed 9 times in the last 48 hours
                      Exceptional! 5.0/5
                      (8 reviews)
                      $71
                      avg/night
                      • Studio
                      • 1 BA
                      • Sleeps 4
                      Cabin #101854
                      8
                      Viewed 13 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
                          Wonderful! 4.9/5
                          (12 reviews)
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 7
                          House #840063vb
                          12
                            Exceptional! 5.0/5
                            (23 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            Cottage #671843vb
                            23
                            Viewed 8 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
                                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
                                  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
                                    Wonderful! 4.8/5
                                    (12 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Cottage #3498723
                                    12
                                    Viewed 16 times in the last 48 hours
                                      Exceptional! 5.0/5
                                      (6 reviews)
                                      $80
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                      Barn #791107vb
                                      6
                                      Viewed 9 times in the last 48 hours
                                        Exceptional! 5.0/5
                                        (29 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 5
                                        Apartment #670504vb
                                        29
                                        Viewed 17 times in the last 48 hours
                                          Excellent! 4.7/5
                                          (21 reviews)
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 6
                                          House #3498716
                                          21
                                          Viewed 12 times in the last 48 hours
                                            Wonderful! 4.8/5
                                            (14 reviews)
                                            avg/night
                                            • 3 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            House #3692712
                                            14
                                            Viewed 5 times in the last 48 hours
                                              Wonderful! 4.9/5
                                              (24 reviews)
                                              avg/night
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 4
                                              Cottage #956783
                                              24
                                              Viewed 7 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (12 reviews)
                                                avg/night
                                                • 5 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 12
                                                House #770571vb
                                                12
                                                Viewed 8 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (19 reviews)
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Apartment #423135vb
                                                  19
                                                  Viewed 15 times in the last 48 hours
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                    Apartment #735099vb
                                                    15
                                                      Excellent! 4.7/5
                                                      (20 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Cottage #104062
                                                      20
                                                      Viewed 9 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (21 reviews)
                                                        $83
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        Cottage #427926vb
                                                        21
                                                        Viewed 16 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (18 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          Cottage #3526439
                                                          18
                                                          Viewed 6 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (18 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            House #479776vb
                                                            18
                                                            Viewed 9 times in the last 48 hours
                                                              Exceptional! 5.0/5
                                                              (19 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              Cottage #671844vb
                                                              19
                                                                Excellent! 4.6/5
                                                                (5 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                Cottage #281249
                                                                5
                                                                Viewed 6 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (12 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 4
                                                                  Cottage #3585233
                                                                  12
                                                                  Viewed 6 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! 4.8/5
                                                                      (9 reviews)
                                                                      $93
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 3
                                                                      Cottage #3772903
                                                                      9
                                                                      Viewed 11 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Townhome #744228vb
                                                                        5
                                                                        Viewed 6 times in the last 48 hours
                                                                          Wonderful! 4.8/5
                                                                          (17 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Cottage #3900896
                                                                          17
                                                                          Viewed 10 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
                                                                              Excellent! 4.7/5
                                                                              (12 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              Chateau / Country House #754684vb
                                                                              12
                                                                              Viewed 19 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
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Cottage #239059
                                                                                  16
                                                                                    Wonderful! 4.8/5
                                                                                    (8 reviews)
                                                                                    avg/night
                                                                                    • 1 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    Cabin #205979
                                                                                    8
                                                                                      Wonderful! 4.8/5
                                                                                      (11 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      Cottage #4107833
                                                                                      11
                                                                                      Viewed 6 times in the last 48 hours
                                                                                        Exceptional! 5.0/5
                                                                                        (18 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Cottage #671845vb
                                                                                        18
                                                                                          Very Good! 4.0/5
                                                                                          (11 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          Condo #4196813
                                                                                          11
                                                                                          Viewed 8 times in the last 48 hours
                                                                                            Excellent! 4.7/5
                                                                                            (10 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 4 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 6
                                                                                            House #3794738
                                                                                            10
                                                                                            Viewed 21 times in the last 48 hours
                                                                                              Wonderful! 4.9/5
                                                                                              (20 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 10
                                                                                              Apartment #743560vb
                                                                                              20
                                                                                              Viewed 11 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (30 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #323254
                                                                                                30
                                                                                                Viewed 12 times in the last 48 hours
                                                                                                  Excellent! 4.7/5
                                                                                                  (11 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 6
                                                                                                  House #3544256
                                                                                                  11
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                  • 1 - 50 of 300+
                                                                                                   

                                                                                                  Recent Islesboro Island Reviews

                                                                                                  Quaint Cottage

                                                                                                  5 of 5
                                                                                                  Natalie, your cottage was just what we were looking for. It was clean, very comfortable and very quiet. The view of the lake was spectacular! We were even lucky enough to see the Albino Stag and doe 3 times! I couldn't believe it. Thank you for making our stay welcoming, J & J
                                                                                                  • Submitted: Nov 3, 2016
                                                                                                  • Stayed: Oct 2016

                                                                                                  Lovely home with beautiful views, quiet and secluded. Great get-away.

                                                                                                  5 of 5
                                                                                                  Comfortably furnished. Very nice master bedroom and bath. 4 bedrooms were all nice and had comfortable beds, but only 3 bathrooms, so 2nd upstairs bedroom occupants had to go downstairs for a bathroom. Kitchen was especially well appointed. A lot of thought by owners went into providing kitchen items, extra towels, beach towels, etc. We enjoyed the deck during the day and evening, plus beachcoming at low tide. Water comes right up to the back yard at high tide. Wished we could have had a working indoor fireplace for chilly nights. Only one small inconvenience - only one TV (in master bedroom) has cable. Other televisions all seem to require your own account/streaming - not that anyone needs TV in such a beautiful setting. However, our group did want to watch the live news (debate) though - so all had to pile into the master bedroom. This is a great location for visiting Acadia National Park, Bar Harbor and on one rainy day we headed to the Farnsworth Museum (about 65 miles away in Rockland) - where it was not raining.
                                                                                                  • Submitted: Nov 2, 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