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

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 7
    House #89636vb
    3
    Viewed 23 times in the last 48 hours
      Excellent! 4.7/5
      (9 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • 1 HF BA
      • Sleeps 6
      Cabin #229559
      9
      Viewed 19 times in the last 48 hours
        Wonderful! 4.9/5
        (12 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 4
        Cottage #735915vb
        12
        Viewed 26 times in the last 48 hours
          Wonderful! 4.9/5
          (28 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 2
          Cottage #483388vb
          28
          Viewed 16 times in the last 48 hours
            avg/night
            • 4 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 10
            House #922474vb
            Viewed 19 times in the last 48 hours
              Excellent! 4.7/5
              (20 reviews)
              avg/night
              • 5 BR
              • 2 BA
              • Sleeps 10
              House #240989
              20
              Viewed 21 times in the last 48 hours
                Wonderful! 4.8/5
                (6 reviews)
                avg/night
                • 4 BR
                • 2 BA
                • Sleeps 10
                House #656978vb
                6
                Viewed 12 times in the last 48 hours
                  Wonderful! 4.8/5
                  (5 reviews)
                  avg/night
                  • 3 BR
                  • 1 BA
                  • 1 HF BA
                  • Sleeps 6
                  Cottage #824406vb
                  5
                  Viewed 17 times in the last 48 hours
                    Wonderful! 4.8/5
                    (12 reviews)
                    avg/night
                    • 3 BR
                    • 1 BA
                    • Sleeps 8
                    House #3805891
                    12
                    Viewed 9 times in the last 48 hours
                      Wonderful! 4.8/5
                      (5 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 9
                      House #494416vb
                      5
                      Viewed 8 times in the last 48 hours
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 6
                        House #928556vb
                          • 5 BR
                          • 4 BA
                          • Sleeps 14
                          House #931023vb
                          1
                          Viewed 59 times in the last 48 hours
                            Exceptional! 5.0/5
                            (5 reviews)
                            avg/night
                            • 2 BR
                            • 2 BA
                            • Sleeps 6
                            House #914110vb
                            5
                            Viewed 34 times in the last 48 hours
                              avg/night
                              • 5 BR
                              • 2 BA
                              • Sleeps 10
                              House #925832vb
                              Viewed 5 times in the last 48 hours
                                Wonderful! 4.8/5
                                (6 reviews)
                                avg/night
                                • 5 BR
                                • 3 BA
                                • Sleeps 13
                                House #255742vb
                                6
                                Viewed 15 times in the last 48 hours
                                  Excellent! 4.6/5
                                  (8 reviews)
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 12
                                  House #3020409
                                  8
                                  Viewed 5 times in the last 48 hours
                                    Excellent! 4.7/5
                                    (45 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Cottage #323435vb
                                    45
                                    Viewed 10 times in the last 48 hours
                                      Wonderful! 4.9/5
                                      (17 reviews)
                                      avg/night
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 8
                                      Cottage #668910vb
                                      17
                                      Viewed 15 times in the last 48 hours
                                        Excellent! 4.4/5
                                        (7 reviews)
                                        avg/night
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 6
                                        House #736164vb
                                        7
                                        Viewed 9 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (30 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 2
                                          Cottage #138154vb
                                          30
                                          Viewed 12 times in the last 48 hours
                                            Excellent! 4.6/5
                                            (7 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            Cottage #132429
                                            7
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Condo #371985vb
                                              23
                                                • Studio
                                                • 1 BA
                                                • Sleeps 2
                                                House #878957vb
                                                4
                                                Viewed 19 times in the last 48 hours
                                                  Wonderful! 4.8/5
                                                  (20 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 5
                                                  House #464656vb
                                                  20
                                                  Viewed 6 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (16 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    House #186651
                                                    16
                                                    Viewed 14 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (12 reviews)
                                                      avg/night
                                                      • 5 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 12
                                                      House #186650vb
                                                      12
                                                      Viewed 6 times in the last 48 hours
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        House #814953vb
                                                        1
                                                        Viewed 7 times in the last 48 hours
                                                          • 4 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          House #763547vb
                                                          4
                                                            Exceptional! 5.0/5
                                                            (8 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 6
                                                            Cottage #879202vb
                                                            8
                                                            Viewed 14 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (17 reviews)
                                                              avg/night
                                                              • 1 BR
                                                              • 1 BA
                                                              • Sleeps 2
                                                              Apartment #923294
                                                              17
                                                              Viewed 8 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (46 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 10
                                                                House #387965vb
                                                                46
                                                                Viewed 13 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (23 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 13
                                                                  House #158384vb
                                                                  23
                                                                  Viewed 16 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (28 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    House #962008
                                                                    28
                                                                    Viewed 23 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (26 reviews)
                                                                      $92
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Cottage #369704vb
                                                                      26
                                                                      Viewed 6 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (5 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Sleeps 6
                                                                        House #295724
                                                                        5
                                                                          Wonderful! 4.9/5
                                                                          (35 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          Apartment #386838vb
                                                                          35
                                                                            Wonderful! 4.9/5
                                                                            (17 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            Cottage #511875vb
                                                                            17
                                                                            Viewed 48 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (13 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 2
                                                                              Apartment #583021vb
                                                                              13
                                                                              Viewed 9 times in the last 48 hours
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                Cottage #3878870
                                                                                4
                                                                                Viewed 13 times in the last 48 hours
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Apartment #862647vb
                                                                                  5
                                                                                    Exceptional! 5.0/5
                                                                                    (21 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    House #912150
                                                                                    21
                                                                                    Viewed 5 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (24 reviews)
                                                                                      avg/night
                                                                                      • 4 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      Cottage #139207vb
                                                                                      24
                                                                                        Excellent! 4.7/5
                                                                                        (14 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 10
                                                                                        House #241372
                                                                                        14
                                                                                        Viewed 15 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (8 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 6
                                                                                          House #581718vb
                                                                                          8
                                                                                          Viewed 9 times in the last 48 hours
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 5
                                                                                            Cottage #593079vb
                                                                                            6
                                                                                              Wonderful! 4.9/5
                                                                                              (14 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              Apartment #24126vb
                                                                                              14
                                                                                              Viewed 7 times in the last 48 hours
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                House #3928994
                                                                                                3
                                                                                                  Exceptional! 5.0/5
                                                                                                  (6 reviews)
                                                                                                  avg/night
                                                                                                  • Studio
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Studio #701115vb
                                                                                                  6
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 4
                                                                                                    Cottage #769769vb
                                                                                                    7
                                                                                                      Exceptional! 5.0/5
                                                                                                      (22 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      House #100243
                                                                                                      22
                                                                                                      Viewed 6 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Squirrel Island Reviews

                                                                                                      Terrific place, great views...

                                                                                                      5 of 5
                                                                                                      This was a great experience. The house is beautiful and so are the views. The kitchen is exceptionally well stocked with settings for 14, including wine glasses, cutting boards, mixers, colanders, larger serving bowls, pitchers and pretty much anything a person could hope to find in a rental home, and the gas fireplace along with the spiral stairs leading to the third floor lookout were a hit with all our guests. I should also mention that the personal service was exceptional, with an owner that answers his own phone.
                                                                                                      • Submitted: Nov 5, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      The Maine of My Dreams

                                                                                                      5 of 5
                                                                                                      I have wanted to see the coast of Maine since I was a kid and my friend went there to see her grandparents! It was all I expected and more. The Friendly Cottage was the PERFECT place to stay for our vacation. The homeaway description and photos were accurate except now there's even a full size dining table. The property was very clean and well stocked. I loved having a washer/dryer too. My husband and I were joined by our two grown sons, their wives and our 4 yr old grandson. There was ample room, a great kitchen (I boiled fresh lobster!!!) and a view that was breathtaking...from the bedroom and living room. We liked being near the end of the island with no visual obstructions to the bay and on to the ocean. We loved being in a community where we could visit with the local residents, watch the lobster fisherman check their traps and learn of their way of life. It's also near great places to visit. Maine Maritime Museum is a must see, we enjoyed lunch in the area general stores, it was an easy drive to Boothbay Harbor where we saw four lighthouses and less than an hour to Portland with Freeport (outlet shopping:) on the way. If I were to return to Maine I would not even consider staying anywhere else. Eric and Laurie live near, welcomed us upon arrival, gave us access to all the property and shore line (relaxing in the red chairs was nothing short of therapeutic), answered our questions about the area, and was available for anything we needed, which was nothing because it was great! Thank you Eric and Laurie! I've already recommended your cottage to several friends who are now considering a Maine vacation.
                                                                                                      • Submitted: Nov 3, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Comfy accomodations in quaint New England Town

                                                                                                      4 of 5
                                                                                                      Kathy, the proprietor is such a friendly person who has done an awesome job with this little inn. We traveled for business and this little place was perfect! Great places to walk around town, easy commute to Portland, gorgeous views out the top floor bedroom and super comfy furniture. Also, there is a Keurig for late night work sessions. We LOVED meeting Kathy's rescue lab, Buddy, who lives downstairs. He sometimes greeted us when we came back in the evening with his sock monkey toy and it just made us smile! Highly recommend for solo travelers, business travelers, couples, or pals on a getaway. Thank you Kathy and family for a great week!
                                                                                                      • Submitted: Oct 25, 2016
                                                                                                      • Stayed: Oct 2016