check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 19 of 19
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (14 reviews)
    avg/night
    • 4 BR
    • 4 BA
    • Sleeps 14
    House #266994vb
    14
    Viewed 18 times in the last 48 hours
      Exceptional! 5.0/5
      (19 reviews)
      avg/night
      • 5 BR
      • 4 BA
      • Sleeps 12
      House #733483vb
      19
      Viewed 17 times in the last 48 hours
        Exceptional! 5.0/5
        (39 reviews)
        avg/night
        • 5 BR
        • 3 BA
        • Sleeps 10
        House #465503vb
        39
        Viewed 24 times in the last 48 hours
          • 4 BR
          • 3 BA
          • 1 HF BA
          • Sleeps 8
          House #358091vb
            Exceptional! 5.0/5
            (28 reviews)
            avg/night
            • 3 BR
            • 2 BA
            • Sleeps 6
            House #962008
            28
            Viewed 44 times in the last 48 hours
              • 5 BR
              • 2 BA
              • 2 HF BA
              • Sleeps 11
              House #3579815
              4
                Wonderful! 4.8/5
                (6 reviews)
                avg/night
                • 4 BR
                • 2 BA
                • Sleeps 10
                House #656978vb
                6
                Viewed 24 times in the last 48 hours
                  Exceptional! 5.0/5
                  (26 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • Sleeps 7
                  House #613606vb
                  26
                  Viewed 10 times in the last 48 hours
                    Excellent! 4.6/5
                    (19 reviews)
                    avg/night
                    • 7 BR
                    • 5 BA
                    • Sleeps 19
                    House #246087vb
                    19
                    Viewed 38 times in the last 48 hours
                      avg/night
                      • 7 BR
                      • 5 BA
                      • 2 HF BA
                      • Sleeps 15
                      House #936968vb
                      Viewed 15 times in the last 48 hours
                        Exceptional! 5.0/5
                        (23 reviews)
                        avg/night
                        • 4 BR
                        • 2 BA
                        • Sleeps 8
                        House #287769
                        23
                        Viewed 8 times in the last 48 hours
                          • 3 BR
                          • 1 BA
                          • 1 HF BA
                          • Sleeps 14
                          House #112112
                          4
                            Exceptional! 5.0/5
                            (7 reviews)
                            avg/night
                            • 4 BR
                            • 2 BA
                            • Sleeps 8
                            House #3818622
                            7
                              Exceptional! 5.0/5
                              (7 reviews)
                              avg/night
                              • 3 BR
                              • 1 BA
                              • 1 HF BA
                              • Sleeps 6
                              House #419566vb
                              7
                                avg/night
                                • 5 BR
                                • 3 BA
                                • Sleeps 12
                                House #325002vb
                                4
                                Viewed 12 times in the last 48 hours
                                  • 6 BR
                                  • 4 BA
                                  • Sleeps 12
                                  House #33280vb
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 6
                                    House #236595
                                    1 Review
                                      • 2 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      House #829978vb
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        House #742537vb
                                        • 1 - 19 of 19
                                         

                                        Recent Bailey Island Reviews

                                        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

                                        Already planning our return!

                                        5 of 5
                                        Our family of 5 LOVED this home. Sherri has paid so much attention to detail and ensures that her guests are extremely comfortable. We were arriving late and she turned on the heat so my kids would not be chilly. As we pulled up, the top floor was illuminated giving the house a "lighthouse" look and we knew we were at the right destination. The kids slept on the top floor and enjoyed the 360 views at sunrise to gently wake them. The antiques, collectables, repurposed items....all of it made this home so charming. Kitchen and linen closets are well supplied, we didn't need to bring anything but whatever we wanted to cook and toiletries, which was great with an already full mini van lol. We cannot wait to come back and are already looking at our calendar. Sherri, thank you, thank you for helping to make my 40th birthday weekend a great one for my family! ps- Cooks was delish!
                                        • Submitted: Oct 17, 2016
                                        • Stayed: Oct 2016

                                        Gracious Hosts!

                                        5 of 5
                                        My wife and I had planned a trip to Orrs & Bailey along with our son and daughter-in-law to celebrate our son's 30th birthday. This was where our son wanted to spend it and it didn't take much arm twisting for us. What we didn't expect was to find ourselves under evacuation orders that week as hurricane Matthew approached our home in Charleston, SC. We needed to get out and called the owners to see if we could possibly check in a day early. They could not have been more gracious and understanding. We enjoyed the most spectacular weather in Maine as we watched the hurricane make landfall in our hometown. All to say -- our heartfelt thanks for this beautiful island get-a-way. Cameras cannot capture the views, the sounds of waves on the rocks, and the sweet scent in the air. Highly recommend this home, and moreover its owners. Thank you!!
                                        • Submitted: Oct 13, 2016
                                        • Stayed: Oct 2016