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

  • 1 - 50 of 300+
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
              • 2 BR
              • 1 BA
              • Sleeps 5
              1 Review
                • 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
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      2 Reviews
                        • 2 BR
                        • 1 HF BA
                        • Sleeps 7
                        1 Review
                          Very Good! 4.0/5
                          (6 reviews)
                          avg/night
                          • 3 BR
                          • 3 BA
                          • Sleeps 6
                          6
                            • 5 BR
                            • 2 BA
                            • Sleeps 11
                            4
                              Wonderful! 4.9/5
                              (38 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 6
                              38
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                4
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  18
                                    Excellent! 4.3/5
                                    (7 reviews)
                                    avg/night
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 4
                                    7
                                      Wonderful! 4.9/5
                                      (9 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      9
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 2
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 5
                                            1 Review
                                              • 2 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 6
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 6
                                                1 Review
                                                  Exceptional! 5.0/5
                                                  (5 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  5
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    2 Reviews
                                                      • 4 BR
                                                      • 1 BA
                                                      • Sleeps 8
                                                      4
                                                        • 5 BR
                                                        • 4 BA
                                                        • 1 HF BA
                                                        • Sleeps 12
                                                          • 3 BR
                                                          • 3 BA
                                                          • Sleeps 6
                                                          1 Review
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 6
                                                            1 Review
                                                              Exceptional! 5.0/5
                                                              (5 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              5
                                                                Exceptional! 5.0/5
                                                                (44 reviews)
                                                                $96
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                44
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  34
                                                                    • 3 BR
                                                                    • 1 BA
                                                                    • Sleeps 6
                                                                    4
                                                                      • 4 BR
                                                                      • 1 BA
                                                                      • Sleeps 9
                                                                        • 4 BR
                                                                        • 5 BA
                                                                        • Sleeps 11
                                                                          Exceptional! 5.0/5
                                                                          (15 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 9
                                                                          15
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            5
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              3
                                                                                • 6 BR
                                                                                • 2 BA
                                                                                • Sleeps 11
                                                                                  Exceptional! 5.0/5
                                                                                  (7 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  7
                                                                                    • 6 BR
                                                                                    • 5 BA
                                                                                    • Sleeps 10
                                                                                    2 Reviews
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 8
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 2
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          1 Review
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 11
                                                                                              12
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 8
                                                                                                4
                                                                                                  Wonderful! 4.9/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  9
                                                                                                    Exceptional! 5.0/5
                                                                                                    (10 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 8
                                                                                                    10
                                                                                                    • 1 - 50 of 300+
                                                                                                     

                                                                                                    Recent Chebeague Island Reviews

                                                                                                    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

                                                                                                    Little Gem by the Sea

                                                                                                    5 of 5
                                                                                                    My husband, our daughter Hannah and I stayed at Shady Potts Point Cottage the weekend of September 17th. The cottage was a cozy, beautiful spot for the last weekend of Summer. There is a lovely sun porch where I had coffee both mornings. The front porch is wonderful to watch the sunset and the sea. There are plenty of opportunities for long walks. Points Point is an easy walk where we enjoyed collecting seashells and just being near the ocean. The cottage has everything you would need to cook meals - and there are several nice restaurants nearby. Dick's Lobster and Crab Shack is a 3 minute walk, where you can get fresh lobster to cook at home. Our mother, who turned 88 that weekend, lives in a senior assisted living facility in Brunswick. We had her birthday party on the sun porch - she is still talking about what a perfect setting and special day it was for her. Thank you for sharing your home with us....I wish I was sitting on the sun porch right now!
                                                                                                    • Submitted: Sep 24, 2016
                                                                                                    • Stayed: Sep 2016