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262 Houses

    31

    6BR Waterfront Estate on Pratt’s Island w/ Bunk House & Loft - Near Dining

    Mid Coast Maine / Southport

    Southport house

    6 14 3 nights min

    • 6 bedrooms
    • sleeps 14
    • 3 nights min
    • Child Friendly
    • Pet Friendly

    Price per night from

    $541

    Price per night from

    $541

      17

      Ledge_The_Southport

      Southport / Newagen

      Newagen house

      3 4 min stay varies

      • 3 bedrooms
      • sleeps 4
      • min stay varies
      • Child Friendly

      Price per night from

      $333

      Price per night from

      $333

        30

        Family Friendly Shoreside 5BR w/ Island View, Near Boothbay Harbor & Downtown

        Mid Coast Maine / Southport

        Southport house

        5 10 min stay varies

        • 5 bedrooms
        • sleeps 10
        • min stay varies
        • Child Friendly
        • Air conditioning

        Price per night from

        $682

        Price per night from

        $682

          17

          Sprucerock_Southport_Island

          Southport / Newagen

          Newagen house

          3 6 min stay varies

          • 3 bedrooms
          • sleeps 6
          • min stay varies
          • Child Friendly
          • Pet Friendly

          Price per night from

          $225

          Price per night from

          $225

            9

            OCEAN WAY ON SOUTHPORT ISLAND | QUIET WOODLAND RETREAT NEAR BEACH

            Mid Coast Maine / Southport

            Southport house

            2 4 14 nights min

            • 2 bedrooms
            • sleeps 4
            • 14 nights min
            • Ask about children
            • Pet Friendly

            Price per night from

            $164

            Price per night from

            $164

              25

              2BR Southport Island Cottage w/ Deck & New Luxe Kitchen, Near Boothbay Harbor

              Mid Coast Maine / Southport

              Southport cottage

              2 6 min stay varies

              • 2 bedrooms
              • sleeps 6
              • min stay varies
              • Child Friendly

              Price per night from

              $87

              Price per night from

              $87

              Great rentals within 20 miles that match your search

              Distance approx 16.06 km from Southport

              (3) Excellent 

                19

                Mazu, the Bed&Boat, the most waterfront cottage

                Mid Coast Maine / Damariscotta

                Damariscotta yacht

                2 6 2 nights min

                • 2 bedrooms
                • sleeps 6
                • 2 nights min
                • Beach / lakeside relaxation
                • Suitable for children age 5+
                • Car not necessary

                Price per night from

                $258

                Price per night from

                $258

                Distance approx 11.06 km from Southport

                (4) Excellent 

                  29

                  Spectacular Ocean Views & Private Beach, Minutes from Popham & Sebasco Resort

                  Mid Coast Maine / Phippsburg

                  Phippsburg house

                  3 8 7 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 7 nights min
                  • Child Friendly
                  • Pet Friendly
                  • Private garden

                  Price per night from

                  $227

                  Price per night from

                  $227

                  Distance approx 13.12 km from Southport

                  (1) Excellent 

                    24

                    "Top of The World Vista" Edgecomb Cottage!

                    Mid Coast Maine / Edgecomb

                    Edgecomb studio

                    Studio 4 min stay varies

                    • Studio
                    • sleeps 4
                    • min stay varies

                    Price per night from

                    $229

                    Responds fast!
                    avg. 8 minutes

                    Price per night from

                    $229

                    Distance approx 8.09 km from Southport

                    (10) Excellent 

                      8

                      Laughton House & Cottages - Cottage

                      Mid Coast Maine / New Harbor

                      New Harbor cottage

                      2 5 3 nights min

                      • 2 bedrooms
                      • sleeps 5
                      • 3 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 0.04 mi
                      • Child Friendly

                      Price per night from

                      $150

                      Responds fast!
                      avg. 19 minutes

                      Price per night from

                      $150

                      Distance approx 19.12 km from Southport

                        20

                        The Barn

                        Mid Coast Maine / Alna

                        Alna house

                        3 12 7 nights min

                        • 3 bedrooms
                        • sleeps 12
                        • 7 nights min
                        • Nearest beach 15 mi
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $344

                        Responds fast!
                        avg. 3 hours 13 minutes

                        Price per night from

                        $344

                        Distance approx 19.06 km from Southport

                        (5) Excellent 

                          20

                          Ocean Front Cottage, Harpswell, ME

                          Mid Coast Maine / Harpswell

                          Harpswell cottage

                          3 6 7 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Pet Friendly

                          Price per night from

                          $255

                          Responds fast!
                          avg. 3 hours 13 minutes

                          Price per night from

                          $255

                          Distance approx 12.71 km from Southport

                            8

                            Vintage Cottage with Spectacular Water Views!

                            Mid Coast Maine / Wiscasset

                            Wiscasset house

                            5 12 3 nights min

                            • 5 bedrooms
                            • sleeps 12
                            • 3 nights min
                            • Child Friendly
                            • Private garden

                            Price per night from

                            $1,140

                            Responds fast!
                            avg. 2 hours 13 minutes

                            Price per night from

                            $1,140

                            Distance approx 16.82 km from Southport

                            (2) Very Good 

                              17

                              Colorful wonderful Penthouse Apartment

                              Mid Coast Maine / Brunswick

                              Brunswick apartment

                              2 3 4 nights min

                              • 2 bedrooms
                              • sleeps 3
                              • 4 nights min
                              • Nearest beach 10 mi
                              • Air conditioning
                              “This is the Penthouse in the Trees--comfortable, close and convenient to town.” I stayed in the apartment on a long term rental for business needs in Brunswick, from September 2014 to the end of January 2015. I experienced 2 of the seasons in the apa
                              …see more

                              Price per night from

                              $110

                              Responds fast!
                              avg. 2 hours 11 minutes

                              Price per night from

                              $110

                              Distance approx 8.43 km from Southport

                                17

                                Happy Hippie Lane Maine: Your Groovy Restore and Explore Midcoast Destination

                                Mid Coast Maine / Wiscasset

                                Wiscasset camper van

                                1 36 1 night min

                                • 1 bedroom
                                • sleeps 36
                                • 1 night min
                                • Nearest beach 32 mi
                                • Child Friendly
                                • Pet Friendly

                                Price per night from

                                $75

                                Price per night from

                                $75

                                Distance approx 9 km from Southport

                                (7) Very Good 

                                  7

                                  Finch Cottage

                                  Mid Coast Maine / New Harbor

                                  New Harbor house

                                  2 4 7 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 7 nights min
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Private garden
                                  “A very enjoyable stay in New Harbor” The Fletchers went out of their way to ensure that we had a good stay at the Finch Cottage. They provided detailed information on things to do and restaurants in the area. They also asked our specific interests a
                                  …see more

                                  Price per night from

                                  $144

                                  Price per night from

                                  $144

                                  Distance approx 6.18 km from Southport

                                  (32) Excellent 

                                    40

                                    Scenic White Rocks Cottage on the Maine Coast

                                    Mid Coast Maine / Georgetown

                                    Georgetown cottage

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Nearest beach 8 mi
                                    • Child Friendly
                                    “Outstanding vacation location on Georgetown Island, Maine” For the past three years, we have vacationed at White Rocks Cottage on Georgetown Island, Maine (not far from Bath) and we highly recommend it. Whether you have children or not, there are ple
                                    …see more

                                    Price per night from

                                    $125

                                    Price per night from

                                    $125

                                    Distance approx 14.18 km from Southport

                                      13

                                      OceanView BonnieView

                                      Mid Coast Maine / Round Pond

                                      Round Pond house

                                      3 8 7 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Child Friendly

                                      Price per night from

                                      $201

                                      Price per night from

                                      $201

                                      Distance approx 3.01 km from Southport

                                        9

                                        Ocean Point, Maine Cottage Weekly Rental

                                        Boothbay / East Boothbay

                                        East Boothbay cottage

                                        2 6 7 nights min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 7 nights min
                                        • Ask about children
                                        • Private garden

                                        Price per night from

                                        $332

                                        Price per night from

                                        $332

                                        Distance approx 11.07 km from Southport

                                        (9) Excellent 

                                          21

                                          Midcoast Waterfront Cottage on Unspoiled Westport Island-3BR/3BA, Fire Pit

                                          Mid Coast Maine / Boothbay Harbor

                                          Boothbay Harbor cottage

                                          3 8 min stay varies

                                          • 3 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Child Friendly
                                          • Private garden

                                          Price per night from

                                          $205

                                          Responds fast!
                                          avg. 46 minutes

                                          Price per night from

                                          $205

                                          Distance approx 2.35 km from Southport Show on Map

                                            23

                                            Waterfront House with Views of Working Harbor and Open Ocean from Every Room

                                            Mid Coast Maine / Georgetown

                                            Georgetown house

                                            4 7 7 nights min

                                            • 4 bedrooms
                                            • sleeps 7
                                            • 7 nights min
                                            • Child Friendly

                                            Price per night from

                                            $324

                                            Price per night from

                                            $324

                                            Distance approx 2.32 km from Southport Show on Map

                                              25

                                              MERWICK COTTAGE | GEORGETOWN, MAINE |WATERFRONT | PRIVATE DOCK AND FLOAT

                                              Mid Coast Maine / Georgetown

                                              Georgetown house

                                              3 6 4 nights min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 4 nights min
                                              • Ask about children
                                              • Pet Friendly

                                              Price per night from

                                              $346

                                              Price per night from

                                              $346

                                              Distance approx 17.16 km from Southport

                                                28

                                                Open Ocean Estate

                                                Maine / Bailey Island

                                                Bailey Island house

                                                3 10 7 nights min

                                                • 3 bedrooms
                                                • sleeps 10
                                                • 7 nights min
                                                • Child Friendly
                                                • Private garden

                                                Price per night from

                                                $604

                                                Price per night from

                                                $604

                                                Distance approx 3.08 km from Southport

                                                (1) Excellent 

                                                  37

                                                  Stunning water views from two family-friendly cottages!

                                                  Mid Coast Maine / Boothbay Harbor

                                                  Boothbay Harbor house

                                                  3 8 2 nights min

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • 2 nights min
                                                  • Child Friendly
                                                  • Car not necessary

                                                  Price per night from

                                                  $278

                                                  Price per night from

                                                  $278

                                                  Distance approx 8.09 km from Southport

                                                  (6) Excellent 

                                                    8

                                                    Laughton House & Cottages - Cabin - Ebb Tide

                                                    Mid Coast Maine / New Harbor

                                                    New Harbor cottage

                                                    1 4 3 nights min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 0.04 mi
                                                    • Child Friendly

                                                    Price per night from

                                                    $126

                                                    Responds fast!
                                                    avg. 19 minutes

                                                    Price per night from

                                                    $126

                                                    Distance approx 8.1 km from Southport

                                                    (27) Excellent 

                                                    Certificate of Excellence

                                                      8

                                                      Laughton House & Cottages - Cabin - Low Tide

                                                      Mid Coast Maine / New Harbor

                                                      New Harbor cottage

                                                      1 3 3 nights min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 3 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 0.04 mi
                                                      • Child Friendly

                                                      Certificate of Excellence

                                                      Price per night from

                                                      $127

                                                      Responds fast!
                                                      avg. 19 minutes

                                                      Price per night from

                                                      $127

                                                      Distance approx 12.71 km from Southport

                                                        27

                                                        Cliffside Cottage on Westport Island, Maine

                                                        Mid Coast Maine / Wiscasset

                                                        Wiscasset converted chapel

                                                        3 6 3 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 3 nights min
                                                        • Child Friendly
                                                        • Private garden

                                                        Price per night from

                                                        $544

                                                        Responds fast!
                                                        avg. 2 hours 13 minutes

                                                        Price per night from

                                                        $544

                                                        Distance approx 7.71 km from Southport

                                                          22

                                                          The Artist's Box : An Adorable Ocean Front Cottage

                                                          Mid Coast Maine / New Harbor

                                                          New Harbor cottage

                                                          3 5 7 nights min

                                                          • 3 bedrooms
                                                          • sleeps 5
                                                          • 7 nights min
                                                          • Private garden

                                                          Price per night from

                                                          $385

                                                          Price per night from

                                                          $385

                                                          Distance approx 2.03 km from Southport

                                                            14

                                                            Capitol Retreat - An Impressive Boothbay Harbor Vacation Home

                                                            Mid Coast Maine / Boothbay Harbor

                                                            Boothbay Harbor house

                                                            4 8 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Pet Friendly
                                                            • Private garden

                                                            Price per night from

                                                            $261

                                                            Price per night from

                                                            $261

                                                            Distance approx 3 km from Southport

                                                            (2) Excellent 

                                                              16

                                                              Charming 1920's cottage in Ocean Point, Maine

                                                              Boothbay / East Boothbay

                                                              East Boothbay cottage

                                                              2 6 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 7 nights min
                                                              • Child Friendly
                                                              • Pet Friendly

                                                              Price per night from

                                                              $164

                                                              Price per night from

                                                              $164

                                                              Distance approx 8.1 km from Southport

                                                              (5) Excellent 

                                                                10

                                                                Laughton House & Cottages - High Tide Cabin

                                                                Mid Coast Maine / New Harbor

                                                                New Harbor cottage

                                                                1 3 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 3
                                                                • 3 nights min
                                                                • Nearest beach 0.06 mi
                                                                • Child Friendly

                                                                Price per night from

                                                                $126

                                                                Responds fast!
                                                                avg. 19 minutes

                                                                Price per night from

                                                                $126

                                                                Distance approx 7.92 km from Southport

                                                                  17

                                                                  SUNRISE | BOOTHBAY | WATER VIEWS | DOCK & FLOAT | VIEWS OF OVENS MOUTH | PET-FRI

                                                                  Mid Coast Maine / Boothbay

                                                                  Boothbay house

                                                                  1 2 4 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 4 nights min
                                                                  • Ask about children
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $289

                                                                  Price per night from

                                                                  $289

                                                                  Distance approx 4.16 km from Southport

                                                                    44

                                                                    Bluewater Vista - Ocean Views, Dock Access, Tennis, Boothbay Harbor

                                                                    Mid Coast Maine / Bayville

                                                                    Bayville cottage

                                                                    4 8 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 8
                                                                    • min stay varies
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $258

                                                                    Price per night from

                                                                    $258

                                                                    Distance approx 3.01 km from Southport

                                                                      9

                                                                      Ocean Peek Cottage

                                                                      Mid Coast Maine / Boothbay Harbor

                                                                      Boothbay Harbor cottage

                                                                      4 7 4 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 7
                                                                      • 4 nights min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $201

                                                                      Price per night from

                                                                      $201

                                                                      Distance approx 6.76 km from Southport

                                                                        20

                                                                        A Writer's Home at the Edge of the Forest on the Boothbay Peninsula

                                                                        Mid Coast Maine / Boothbay

                                                                        Boothbay house

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $149

                                                                        Price per night from

                                                                        $149

                                                                        Distance approx 17.68 km from Southport

                                                                          4

                                                                          Meadow View Artist Retreat

                                                                          Maine / Monhegan Island

                                                                          Monhegan Island apartment

                                                                          1 2 3 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 3 nights min
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $229

                                                                          Price per night from

                                                                          $229

                                                                          Distance approx 9.21 km from Southport

                                                                          (6) Excellent 

                                                                            21

                                                                            Victorian Cottage on Westport Island

                                                                            Mid Coast Maine / Wiscasset

                                                                            Wiscasset cottage

                                                                            4 8 3 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 3 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Private garden

                                                                            Price per night from

                                                                            $229

                                                                            Price per night from

                                                                            $229

                                                                            Distance approx 5.4 km from Southport

                                                                            (8) Excellent 

                                                                              22

                                                                              Georgetown (Back River) Vacation Home

                                                                              Mid Coast Maine / Georgetown

                                                                              Georgetown house

                                                                              5 10 7 nights min

                                                                              • 5 bedrooms
                                                                              • sleeps 10
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $282

                                                                              Responds fast!
                                                                              avg. 3 hours 39 minutes

                                                                              Price per night from

                                                                              $282