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
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!

Winter Harbor: Houses, Cottages & More (300+)

  • 1 - 50 of 300+
Additional fees apply. Taxes may be added.
    • 1 BR
    • 2 BA
    • Sleeps 4
      • 3 BR
      • 2 BA
      • Sleeps 7
      21
        • 3 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 10
        20
          • 3 BR
          • 1 BA
          • Sleeps 6
          21
            Exceptional! 5.0/5
            (12 reviews)
            avg/night
            • 4 BR
            • 1 BA
            • 1 HF BA
            • Sleeps 9
            12
              Exceptional! 5.0/5
              (15 reviews)
              View details for price
              • 3 BR
              • 3 BA
              • 1 HF BA
              • Sleeps 6
              15
                Wonderful! 4.9/5
                (10 reviews)
                avg/night
                • 5 BR
                • 3 BA
                • 1 HF BA
                • Sleeps 10
                10
                  • 4 BR
                  • 4 BA
                  • 1 HF BA
                  • Sleeps 8
                  1 Review
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    3
                      Exceptional! 5.0/5
                      (5 reviews)
                      avg/night
                      • 2 BR
                      • 2 BA
                      • Sleeps 6
                      5
                        • 4 BR
                        • 1 BA
                        • Sleeps 7
                        2 Reviews
                          Wonderful! 4.8/5
                          (6 reviews)
                          View details for price
                          • 4 BR
                          • 2 BA
                          • Sleeps 10
                          6
                            Excellent! 4.4/5
                            (11 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            11
                              • 2 BR
                              • 2 BA
                              • Sleeps 5
                              3
                                Excellent! 4.3/5
                                (11 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 5
                                11
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  3
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 4
                                    2 Reviews
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 3
                                      6
                                        Wonderful! 4.9/5
                                        (7 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        7
                                          • 6 BR
                                          • 4 BA
                                          • Sleeps 8
                                          5
                                            NEW!
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 10
                                            1 Review
                                              NEW!
                                              • 1 BR
                                              • 1 BA
                                              • Sleeps 2
                                              1 Review
                                                • 3 BR
                                                • 1 BA
                                                • Sleeps 7
                                                4
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 7
                                                  4
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 8
                                                    2 Reviews
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      2 Reviews
                                                        NEW!
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        3
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          4
                                                            • 3 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 7
                                                            7
                                                              • 4 BR
                                                              • 1 BA
                                                              • 1 HF BA
                                                              • Sleeps 8
                                                              27
                                                                Wonderful! 4.9/5
                                                                (18 reviews)
                                                                avg/night
                                                                • 4 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 12
                                                                18
                                                                  • 3 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  7
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    7
                                                                      Wonderful! 4.9/5
                                                                      (7 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      7
                                                                        Excellent! 4.7/5
                                                                        (16 reviews)
                                                                        avg/night
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 10
                                                                        16
                                                                          Wonderful! 4.8/5
                                                                          (6 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          6
                                                                            Exceptional! 5.0/5
                                                                            (13 reviews)
                                                                            avg/night
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 6
                                                                            13
                                                                              Excellent! 4.5/5
                                                                              (15 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              15
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 8
                                                                                6
                                                                                  • 3 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 6
                                                                                  20
                                                                                    Wonderful! 4.8/5
                                                                                    (12 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    12
                                                                                      • 5 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                      7
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        6
                                                                                          Excellent! 4.7/5
                                                                                          (23 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                          23
                                                                                            Wonderful! 4.8/5
                                                                                            (9 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            9
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 2
                                                                                              32
                                                                                                Wonderful! 4.9/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 7
                                                                                                11
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  25
                                                                                                    Exceptional! 5.0/5
                                                                                                    (10 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • 2 HF BA
                                                                                                    • Sleeps 6
                                                                                                    10
                                                                                                      Exceptional! 5.0/5
                                                                                                      (10 reviews)
                                                                                                      avg/night
                                                                                                      • 3 BR
                                                                                                      • 1 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 6
                                                                                                      10
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Winter Harbor Reviews

                                                                                                      great value for the price

                                                                                                      4 of 5
                                                                                                      Dragonwood castle is a magical place and we enjoyed our stay very much. The location and view were spectacular as described. You awake to see the sunrise over the water from the third floor bedroom and listen to the waves as you fall asleep. We enjoyed launching our kayak from the front yard. The second floor is more like one big room with a double bed and crib on one half and two twins and a reading/nap nook in the other half. There is not the privacy of two separate bedrooms. Nearby restaurants close by 7 (and stop serving earlier); a late dinner requires a drive -- 30 minutes to Ellsworth or about an hour to Bar Harbor. The kitchen is clean and well stocked, although the spices are old and have lost their piquancy. The house is very clean although there is a musty smell, which adds to the "castle" ambiance, and a few spiderwebs in hard-to-reach places. We would definitely stay here again. It's a great value for the price.
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Fantastic Vacation Rental!

                                                                                                      5 of 5
                                                                                                      We thoroughly enjoyed our week-long stay. The house was perfectly located in downtown Bar Harbor, within easy walking distance to all the shops, restaurants and buses. We spent much of our time hiking in Acadia National Park, which is a short drive away. The house was described perfectly and the pictures showed exactly how the house looked. It's a old house with tons of charm and character and has all of the modern conveniences you could want. The washer/dryer, dishwasher, and tankless water heater were a huge plus! There were even board games, puzzles and books which were fun for a rainy afternoon. There was plenty of room to accommodate a large group. We had five people and there was definitely room to spare. Julie was great to deal with as far as any questions we had before arriving and there was a great information packet waiting for us when we got there. We would love to stay here again and would highly recommend this house to anyone looking to stay in Bar Harbor.
                                                                                                      • Submitted: Sep 21, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Great seaside vacation home.

                                                                                                      5 of 5
                                                                                                      What a great home to rent when visiting down east Maine. Thank You for offering a spacious, clean, fun home. Great for families and friends, the kitchen and dexk combo make a great place to power down for the day. A short walk to the local eateries and to the ferry to Bar Harbor make this a great home base. And next to georgeous Schoodic peninsula, we will be back.
                                                                                                      • Submitted: Sep 17, 2016
                                                                                                      • Stayed: Sep 2016