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Chebeague Island: House Rentals (334)

  • 1 - 50 of 334
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 8
    4
      NEW!
      • 3 BR
      • 2 BA
      • Sleeps 8
        NEW!
        • 3 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 6
          NEW!
          • 2 BR
          • 1 BA
          • Sleeps 5
            • 4 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 12
            3
              NEW!
              • 4 BR
              • 2 BA
              • Sleeps 9
                • 3 BR
                • 2 BA
                • Sleeps 6
                2 Reviews
                  • 3 BR
                  • 3 BA
                  • Sleeps 6
                  6
                    • 5 BR
                    • 2 BA
                    • Sleeps 11
                    4
                      • 2 BR
                      • 1 BA
                      • Sleeps 6
                      38
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        18
                          • 3 BR
                          • 2 BA
                          • Sleeps 6
                          4
                            • 2 BR
                            • 1 BA
                            • Sleeps 5
                            1 Review
                              • 4 BR
                              • 1 BA
                              • Sleeps 8
                              4
                                NEW!
                                • 5 BR
                                • 4 BA
                                • 1 HF BA
                                • Sleeps 12
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  1 Review
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 6
                                    2 Reviews
                                      • 4 BR
                                      • 1 BA
                                      • Sleeps 9
                                        NEW!
                                        • 4 BR
                                        • 5 BA
                                        • Sleeps 11
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 9
                                          13
                                            NEW!
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                              • 6 BR
                                              • 2 BA
                                              • Sleeps 11
                                                • 6 BR
                                                • 5 BA
                                                • Sleeps 10
                                                2 Reviews
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 8
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 11
                                                    11
                                                      • 4 BR
                                                      • 3 BA
                                                      • Sleeps 8
                                                      4
                                                        • 4 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        21
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 10
                                                            • 4 BR
                                                            • 4 BA
                                                            • Sleeps 8
                                                            5
                                                              NEW!
                                                              • 3 BR
                                                              • 2 BA
                                                              • 1 HF BA
                                                              • Sleeps 6
                                                              2 Reviews
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                1 Review
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 7
                                                                  21
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    5
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      2 Reviews
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                          • 5 BR
                                                                          • 2 BA
                                                                          • Sleeps 15
                                                                          9
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            25
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              5
                                                                                • 7 BR
                                                                                • 5 BA
                                                                                • Sleeps 19
                                                                                19
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 4
                                                                                  7
                                                                                    • 2 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 5
                                                                                    3
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      5
                                                                                        • 3 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 6
                                                                                        5
                                                                                          NEW!
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          2 Reviews
                                                                                            NEW!
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 10
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              21
                                                                                                NEW!
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  7
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
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                                                                                                    • 1 - 50 of 334
                                                                                                     

                                                                                                    Recent Chebeague Island Reviews

                                                                                                    Little piece of heaven

                                                                                                    5 of 5
                                                                                                    Our stay on Bailey island was spectacular. We stayed with Laurie and Eric last year for a shorter stay in their smaller rental. That was very comfortable, clean (like new) with a great view. We decided to return this year, 2016 and stay in Friendly Cottage. There are beautiful views from every window, large wonderfully decorated spacious rooms. Everything you need is there. We have actually booked our 2017 vacation for next year. We can't wait to return to Bailey Island, the untouched gem of a place to vacation.
                                                                                                    • Submitted: Aug 31, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Even better than expected!

                                                                                                    5 of 5
                                                                                                    Underoaks is the perfect setting to relax and unwind. The waterviews from the house are spectacular! The kids really enjoyed climbing on the rocks at the beach. The house is spacious, and even with 11 of us, there was plenty of room to all be together or to have private time. Portland and Freeport are only a shirt drive away if interested in shopping or going out to eat. Jenny was great about getting in touch through email or phone and offered great suggestions for things to do. We will definitely be looking into reserving the house again in the future!
                                                                                                    • Submitted: Aug 14, 2016
                                                                                                    • Stayed: Jul 2016

                                                                                                    A clean, comfy & very homey abode in a wonderful neighborhood.

                                                                                                    5 of 5
                                                                                                    From the outset both Monique & Matt were very gracious & open. The home is very well appointed & furnished including 2 gorgeous outdoor seating areas. The first floor plan is nice & open, and the bedrooms on the second floor offer lots of privacy. Falmouth is close enough to Portland (in Old Port in 20 minutes, 25 with "traffic" lol), and even places like Boothbay Harbor are only an hour away via car - which makes for some nice day trips. The fenced backyard was a great little playground for Ruby (our welsh springer) and she enjoyed the nice strolls down to the water's edge. I recommend you bring a couple box fans to pull in the wonderful Maine fresh air. There are nice circulating fans located throughout the house so you just need a way to draw in the outdoor air.
                                                                                                    • Submitted: Aug 13, 2016
                                                                                                    • Stayed: Aug 2016