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Chebeague Island: Houses, Cottages & More (722)

  • 1 - 50 of 722
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 8
    5
      • 3 BR
      • 2 BA
      • Sleeps 5
      2 Reviews
        • 3 BR
        • 2 BA
        • Sleeps 8
          Exceptional! 5.0/5
          (6 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 6
          6
            • 3 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 6
              NEW!
              • 2 BR
              • 1 BA
              • Sleeps 5
              1 Review
                NEW!
                • 3 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 6
                  • 4 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 12
                  3
                    • 4 BR
                    • 2 BA
                    • Sleeps 9
                      Excellent! 4.3/5
                      (7 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 4
                      7
                        • 2 BR
                        • 1 BA
                        • Sleeps 6
                        34
                          Exceptional! 5.0/5
                          (44 reviews)
                          $96
                          avg/night
                          • 1 BR
                          • 1 BA
                          • Sleeps 4
                          44
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            2 Reviews
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              4
                                Very Good! 4.0/5
                                (6 reviews)
                                avg/night
                                • 3 BR
                                • 3 BA
                                • Sleeps 6
                                6
                                  Exceptional! 5.0/5
                                  (5 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  5
                                    NEW!
                                    • 5 BR
                                    • 4 BA
                                    • 1 HF BA
                                    • Sleeps 12
                                      Wonderful! 4.9/5
                                      (9 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      9
                                        Exceptional! 5.0/5
                                        (7 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        7
                                          Exceptional! 5.0/5
                                          (15 reviews)
                                          avg/night
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 9
                                          15
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            18
                                              • 2 BR
                                              • 1 HF BA
                                              • Sleeps 7
                                              1 Review
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 5
                                                1 Review
                                                  Wonderful! 4.9/5
                                                  (38 reviews)
                                                  avg/night
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 6
                                                  38
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    2 Reviews
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      3
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 7
                                                        24
                                                          • 5 BR
                                                          • 2 BA
                                                          • Sleeps 11
                                                          4
                                                            Wonderful! 4.9/5
                                                            (9 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            9
                                                              Wonderful! 4.9/5
                                                              (10 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 4
                                                              10
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                27
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 6
                                                                  4
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                      Very Good! 4.0/5
                                                                      (7 reviews)
                                                                      $86
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 2
                                                                      7
                                                                        Excellent! 4.6/5
                                                                        (19 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • Sleeps 6
                                                                        19
                                                                          Exceptional! 5.0/5
                                                                          (9 reviews)
                                                                          avg/night
                                                                          • 1 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          9
                                                                            Wonderful! 4.9/5
                                                                            (18 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 1 BA
                                                                            • Sleeps 6
                                                                            18
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              8
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                22
                                                                                  NEW!
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  1 Review
                                                                                    Exceptional! 5.0/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 8
                                                                                    5
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      4
                                                                                        Exceptional! 5.0/5
                                                                                        (5 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        5
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                            1 Review
                                                                                              Excellent! 4.4/5
                                                                                              (5 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 1 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 5
                                                                                              5
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                8
                                                                                                  Exceptional! 5.0/5
                                                                                                  (10 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  10
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 5
                                                                                                    3
                                                                                                    • 1 - 50 of 722
                                                                                                     

                                                                                                    Recent Chebeague Island Reviews

                                                                                                    East Portland Haven

                                                                                                    5 of 5
                                                                                                    This property and location are very nice. It is spacious, colorful, nice linens, clean and the location is just right. We enjoyed the East Promenade, the ability to walk to Old Port and the lovely neighborhood.
                                                                                                    • Submitted: Sep 27, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    Perfect Maine Cottage!

                                                                                                    5 of 5
                                                                                                    A few girlfriends and I had a kid-free getaway celebrating our 40th birthdays! We chose this sweet little cottage in Maine because of it's central location. We were able to go shopping at the outlets in Freeport, wine-tasting, and hiking all very conveniently from this location. Portland was so close, it was really easy to go to dinner there too. The best part was on my friend's actual birthday, we bought steamed lobsters and corn at the town landing store (along with some wine!) and brought some beach chairs from the house and sat at the local beach and watched the sunset while having a feast! The cottage was low-key, beautifully decorated and had everything we needed. I would love to go back with my family and even bring the kids next time!
                                                                                                    • Submitted: Sep 26, 2016
                                                                                                    • Stayed: Jul 2016

                                                                                                    Relaxing get away

                                                                                                    5 of 5
                                                                                                    We thoroughly enjoyed our stay on Chebeague Island. The house was comfortable and well stocked. We brought clothes and some food with us and the house had everything else we needed. The island is a great place to explore on foot or bike. Use of a vehicle during our stay was just a luxury. For the days we didn't feel like exploring, the house was a perfect place to relax. Patrica was wonderful to work with. She was always responsive to any questions and kindly checked in by email to see if there was anything we needed. If you're looking for a home base to explore the island or just relax, I would highly recommend this house.
                                                                                                    • Submitted: Sep 25, 2016
                                                                                                    • Stayed: Sep 2016