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  • Showing 1-50 of 300+
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    avg/night
    • 4 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 12
    House #3540922
    3
    Viewed 13 times in the last 48 hours
      Exceptional! 5/5
      (6 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 6
      Farmhouse #4055121
      6
      Viewed 36 times in the last 48 hours
        • 3 BR
        • 1 BA
        • 1 HF BA
        • Sleeps 8
        House #3801704
        5
          avg/night
          • 3 BR
          • 2 BA
          • Sleeps 5
          House #628732vb
          2
          Viewed 5 times in the last 48 hours
            Wonderful! 4.9/5
            (37 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 6
            Cottage #144916
            37
            Viewed 86 times in the last 48 hours
              Excellent! 4.5/5
              (4 reviews)
              avg/night
              • 4 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 8
              House #4232093
              4
              Viewed 39 times in the last 48 hours
                Wonderful! 4.9/5
                (77 reviews)
                avg/night
                • 3 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 5
                Cottage #953622
                77
                Viewed 58 times in the last 48 hours
                  $42
                  avg/night
                  • 1 BR
                  • 1 BA
                  • Sleeps 2
                  Apartment #4222309
                  1
                  Viewed 24 times in the last 48 hours
                    Exceptional! 5/5
                    (33 reviews)
                    avg/night
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    Apartment #3967410
                    33
                    Viewed 145 times in the last 48 hours
                      Wonderful! 4.9/5
                      (15 reviews)
                      avg/night
                      • 4 BR
                      • 3 BA
                      • 2 HF BA
                      • Sleeps 10
                      House #852940vb
                      15
                      Viewed 97 times in the last 48 hours
                        Wonderful! 4.8/5
                        (30 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 2
                        Cottage #138154vb
                        30
                        Viewed 112 times in the last 48 hours
                          Exceptional! 5/5
                          (26 reviews)
                          avg/night
                          • 4 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 10
                          House #699034vb
                          26
                          Viewed 101 times in the last 48 hours
                            Exceptional! 5/5
                            (29 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 8
                            House #3785458
                            29
                            Viewed 87 times in the last 48 hours
                              Excellent! 4.6/5
                              (19 reviews)
                              avg/night
                              • 1 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 5
                              Condo #3944741
                              19
                              Viewed 53 times in the last 48 hours
                                Exceptional! 5/5
                                (65 reviews)
                                avg/night
                                • Studio
                                • 1 BA
                                • Sleeps 2
                                Apartment #3780374
                                65
                                Viewed 53 times in the last 48 hours
                                  Wonderful! 4.9/5
                                  (23 reviews)
                                  $92
                                  avg/night
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 6
                                  Condo #3538570
                                  23
                                  Viewed 46 times in the last 48 hours
                                    Wonderful! 4.9/5
                                    (32 reviews)
                                    avg/night
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 4
                                    Cottage #656539vb
                                    32
                                    Viewed 40 times in the last 48 hours
                                      Excellent! 4.6/5
                                      (13 reviews)
                                      avg/night
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                      Condo #4238604
                                      13
                                      Viewed 37 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (30 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 2
                                        Apartment #499096vb
                                        30
                                        Viewed 40 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (40 reviews)
                                          $95
                                          avg/night
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 4
                                          House #3827615
                                          40
                                          Viewed 47 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (19 reviews)
                                            avg/night
                                            • 2 BR
                                            • 1 BA
                                            • Sleeps 6
                                            Apartment #897262vb
                                            19
                                            Viewed 63 times in the last 48 hours
                                              Exceptional! 5/5
                                              (83 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • 1 HF BA
                                              • Sleeps 4
                                              Bungalow #973608
                                              83
                                              Viewed 63 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (21 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Bungalow #669441vb
                                                21
                                                Viewed 42 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (16 reviews)
                                                  $94
                                                  avg/night
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  Apartment #24126vb
                                                  16
                                                  Viewed 59 times in the last 48 hours
                                                    Exceptional! 5/5
                                                    (7 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 1 BA
                                                    • 1 HF BA
                                                    • Sleeps 6
                                                    Cottage #833864vb
                                                    7
                                                    Viewed 23 times in the last 48 hours
                                                      Exceptional! 5/5
                                                      (30 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Apartment #3953635
                                                      30
                                                      Viewed 25 times in the last 48 hours
                                                        Excellent! 4.4/5
                                                        (8 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 4
                                                        Cottage #192030
                                                        8
                                                        Viewed 43 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (12 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          House #12490vb
                                                          12
                                                          Viewed 20 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (12 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 5
                                                            Cottage #3897642
                                                            12
                                                            Viewed 80 times in the last 48 hours
                                                              avg/night
                                                              • 2 BR
                                                              • 2 BA
                                                              • Sleeps 4
                                                              House #4053524
                                                              3
                                                              Viewed 19 times in the last 48 hours
                                                                Exceptional! 5/5
                                                                (28 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                House #962008
                                                                28
                                                                Viewed 85 times in the last 48 hours
                                                                  Wonderful! 4.9/5
                                                                  (19 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 HF BA
                                                                  • Sleeps 4
                                                                  Townhome #3723457
                                                                  19
                                                                  Viewed 27 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (18 reviews)
                                                                    avg/night
                                                                    • 4 BR
                                                                    • 3 BA
                                                                    • Sleeps 8
                                                                    Cottage #668910vb
                                                                    18
                                                                    Viewed 66 times in the last 48 hours
                                                                      Excellent! 4.5/5
                                                                      (4 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      Cottage #885706vb
                                                                      4
                                                                      Viewed 34 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (26 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 10
                                                                        House #232136
                                                                        26
                                                                        Viewed 61 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (37 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 HF BA
                                                                          • Sleeps 4
                                                                          Townhome #3684592
                                                                          37
                                                                          Viewed 28 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (49 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 2 BA
                                                                            • Sleeps 13
                                                                            House #333300vb
                                                                            49
                                                                            Viewed 58 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (13 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Cottage #735915vb
                                                                              13
                                                                              Viewed 40 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (10 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 6
                                                                                House #746656vb
                                                                                10
                                                                                Viewed 42 times in the last 48 hours
                                                                                  Exceptional! 5/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 5
                                                                                  House #914110vb
                                                                                  6
                                                                                  Viewed 75 times in the last 48 hours
                                                                                    Exceptional! 5/5
                                                                                    (19 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    House #714816vb
                                                                                    19
                                                                                    Viewed 44 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Apartment #4208745
                                                                                      10
                                                                                      Viewed 41 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (17 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Cottage #608554vb
                                                                                        17
                                                                                        Viewed 37 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (18 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          Cottage #3001385
                                                                                          18
                                                                                          Viewed 73 times in the last 48 hours
                                                                                            Exceptional! 5/5
                                                                                            (52 reviews)
                                                                                            avg/night
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 4
                                                                                            Apartment #3780005
                                                                                            52
                                                                                            Viewed 42 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (10 reviews)
                                                                                              avg/night
                                                                                              • 5 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 15
                                                                                              House #150051
                                                                                              10
                                                                                              Viewed 36 times in the last 48 hours
                                                                                                Exceptional! 5/5
                                                                                                (21 reviews)
                                                                                                avg/night
                                                                                                • 5 BR
                                                                                                • 4 BA
                                                                                                • Sleeps 12
                                                                                                House #3751251
                                                                                                21
                                                                                                Viewed 137 times in the last 48 hours
                                                                                                  Exceptional! 5/5
                                                                                                  (29 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Condo #871843vb
                                                                                                  29
                                                                                                  Viewed 48 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (34 reviews)
                                                                                                    avg/night
                                                                                                    • 2 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    Cottage #165589vb
                                                                                                    34
                                                                                                    Viewed 61 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (11 reviews)
                                                                                                      avg/night
                                                                                                      • 1 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Apartment #711180vb
                                                                                                      11
                                                                                                      Viewed 39 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Chebeague Island: Vacation Rentals (540)

                                                                                                       

                                                                                                      Recent Chebeague Island Reviews

                                                                                                      A perfect winter getaway!

                                                                                                      5 of 5
                                                                                                      We loved this house - it was perfect for a couple who wanted a quiet winter weekend! We loved the proximity to the water, even if we had to climb over piles of snow to see it! The area was a beautiful winter wonderland. It is in a true neighborhood - many families walking with dogs, a nice little coffee shop, and lots of quiet and opportunity to relax. There is not much in South Portland in terms of restaurants and night-life, but we were a quick 10 minute drive to downtown Portland, so we got our fill :) We were so pleased with the communication with the owner before we arrived - thank you!! We can't wait to be back!
                                                                                                      • Submitted: Feb 20, 2017
                                                                                                      • Stayed: Feb 2017

                                                                                                      Beautiful property, great location, sleek design

                                                                                                      5 of 5
                                                                                                      We had a wonderful weekend in Portland Maine. The property is right in the heart of old Portland with beautiful views of downtown and the harbor. The apartment is a beautiful blend of old and new, with brick walls and high end finishes, chic bathrooms, and a great lookout tower for cocktails. Check in and out were a breeze.
                                                                                                      • Submitted: Feb 15, 2017
                                                                                                      • Stayed: Feb 2017

                                                                                                      A lovely home

                                                                                                      5 of 5
                                                                                                      We really enjoyed our stay in this South Portland home. We were in town for a family get-together and found this house very comfortable in every way. The rooms were spacious and nicely decorated. The beds were comfortable and the linens and pillows high quality. Unlike many other rentals we have visited, this one included so many essentials, like dish soap, toilet paper, paper towels and trash bags. The manager was accommodating and helpful when we needed an early check-in time. The kitchen is beautiful and modern and very well stocked with terrific cooking tools, including sharp knives! The 2 1/2 bathrooms were beautiful, and the whole place was spotlessly clean. My daughter had to work from the house one day, and found the little desk/computer area in one of the sunny bedrooms just delightful and efficient. Another plus is port-a-crib, changing table and high chair, which we didn't need this trip but maybe next time. A great location too, close to Willard Beach and an easy drive to Portland and the airport. We hope to be able to come back soon. Thank you for making our stay so enjoyable!
                                                                                                      • Submitted: Jan 29, 2017
                                                                                                      • Stayed: Jan 2017