Winter Harbor Rentals

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482 Houses

(46) Excellent 

Certificate of Excellence

    58

    ACADIA National Park. Walk to Ocean, Restaurants. Private Deck w/Mountain View

    DownEast and Acadia Maine / Winter Harbor

    Winter Harbor house

    3 6 min stay varies

    • 3 bedrooms
    • sleeps 6
    • min stay varies
    • Nearest beach 0.2 mi
    • Child Friendly
    • Private garden
    “Comfy and Clean” Our family of five just returned from staying five nights in Winter Harbor. The stay was wonderful and the house was really great. We all felt so at home. The house was spotlessly clean. The neighborhood was very friendly. The ow
    …see more

    Certificate of Excellence

    Map

    Price per night from

    $149

    Responds fast!
    avg. 1 hour 9 minutes

    Price per night from

    $149

    Details
      9

      Gerrish Vacation Rentals

      DownEast and Acadia Maine / Winter Harbor

      Winter Harbor apartment

      1 2 5 nights min

      • 1 bedroom
      • sleeps 2
      • 5 nights min
      • Child Friendly
      • Pet Friendly

      Map

      Price per night from

      $166

      Price per night from

      $166

      Details
        8

        Gerrish Vacation Rentals

        DownEast and Acadia Maine / Winter Harbor

        Winter Harbor apartment

        1 2 7 nights min

        • 1 bedroom
        • sleeps 2
        • 7 nights min
        • Child Friendly
        • Pet Friendly
        • Private garden

        Map

        Price per night from

        $166

        Price per night from

        $166

        Details
          10

          Down East Maine Modern, Well Equipped Cottage in Heart of Coastal Winter Harbor

          DownEast and Acadia Maine / Winter Harbor

          Winter Harbor cottage

          2 5 7 nights min

          • 2 bedrooms
          • sleeps 5
          • 7 nights min
          • Nearest beach 3 mi
          • Child Friendly
          • Private garden

          Map

          Price per night from

          $177

          Price per night from

          $177

          Details
            15

            Acadia, Schoodic Peninsula, Henry's Cove Home

            DownEast and Acadia Maine / Winter Harbor

            Winter Harbor house

            3 6 5 nights min

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

            Map

            Price per night from

            $212

            Price per night from

            $212

            Details
              24

              Rustic Waterfront Cabin w/ Beach in Winter Harbor!

              DownEast and Acadia Maine / Winter Harbor

              Winter Harbor log cabin

              3 6 4 nights min

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

              Map

              Price per night from

              $178

              Responds fast!
              avg. 9 minutes

              Price per night from

              $178

              Details

              (5) Excellent 

                21

                Captain Guptill House steps from the waters edge in Winter Harbor

                DownEast and Acadia Maine / Winter Harbor

                Winter Harbor house

                3 6 7 nights min

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

                Map

                Price per night from

                $253

                Responds fast!
                avg. 25 minutes

                Price per night from

                $253

                Details

                (3) Excellent 

                  25

                  Guptill Cottage on Schoodic Point, Winter Harbor

                  DownEast and Acadia Maine / Winter Harbor

                  Winter Harbor house

                  3 5 7 nights min

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

                  Map

                  Price per night from

                  $205

                  Responds fast!
                  avg. 25 minutes

                  Price per night from

                  $205

                  Details

                  (2) Very Good 

                    26

                    Captain Bickford House (Arthur Frommer was here)

                    DownEast and Acadia Maine / Winter Harbor

                    Winter Harbor house

                    2 6 7 nights min

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

                    Map

                    Price per night from

                    $136

                    Price per night from

                    $136

                    Details

                    Great rentals within 20 miles that match your search

                    Distance approx 13.8 km from Winter Harbor

                    (8) Excellent 

                    Certificate of Excellence

                      21

                      Evergreen Hill | Cape style home with attached Cabin

                      Mount Desert Island / Southwest Harbor

                      Southwest Harbor house

                      3 9 min stay varies

                      • 3 bedrooms
                      • sleeps 9
                      • min stay varies
                      • Child Friendly
                      • Private garden

                      Certificate of Excellence

                      Price per night from

                      $184

                      Price per night from

                      $184

                      Details

                      Distance approx 17.16 km from Winter Harbor

                      (2) Excellent 

                        9

                        Quarterdeck 2 bedroom shore front fabulous sunsets

                        DownEast and Acadia Maine / Trenton

                        Trenton cottage

                        2 4 7 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 7 nights min
                        • Beach / lakeside relaxation
                        • Child Friendly
                        • Ask about pets

                        Price per night from

                        $245

                        Price per night from

                        $245

                        Details

                        Distance approx 11.07 km from Winter Harbor

                        (3) Excellent 

                          23

                          Picture Perfect Bar Harbor Log Cabin

                          Mount Desert Island / Bar Harbor

                          Bar Harbor house

                          3 6 7 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 7 nights min
                          • Child Friendly
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $401

                          Price per night from

                          $401

                          Details

                          Distance approx 17.46 km from Winter Harbor

                          (1) Excellent 

                            8

                            Sea Watch 3 bedroom at Sawyer's Cove path to shore

                            Mount Desert Island / Southwest Harbor

                            Southwest Harbor cottage

                            3 6 7 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Ask about pets

                            Price per night from

                            $311

                            Price per night from

                            $311

                            Details

                            Distance approx 3.32 km from Winter Harbor

                              32

                              ‘Dragonwood Castle’ 3BR Maine Home on Waterfront!

                              Gouldsboro / Prospect Harbor

                              Prospect Harbor cottage

                              3 7 min stay varies

                              • 3 bedrooms
                              • sleeps 7
                              • min stay varies
                              • Child Friendly
                              • Pet Friendly

                              Price per night from

                              $264

                              Responds fast!
                              avg. 10 minutes

                              Price per night from

                              $264

                              Details

                              Distance approx 9.57 km from Winter Harbor

                                16

                                Serenity - Acadia

                                Mount Desert Island / Bar Harbor

                                Bar Harbor house

                                4 8 7 nights min

                                • 4 bedrooms
                                • sleeps 8
                                • 7 nights min
                                • Child Friendly
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $241

                                Price per night from

                                $241

                                Details

                                Distance approx 16.95 km from Winter Harbor

                                (35) Excellent 

                                Certificate of Excellence

                                  20

                                  Tranquility Cottage

                                  Mount Desert Island / Acadia National Park

                                  Acadia National Park house

                                  3 6 min stay varies

                                  • 3 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Child Friendly
                                  • Private garden
                                  “Excellent quiet get away, near a beautiful park!” My boyfriend and I stayed here in early October as a get away from our busy lives as medical residents, and we couldnt have been happier with our choice! Julie is an excellent owner, she sent us intric
                                  …see more

                                  Certificate of Excellence

                                  Price per night from

                                  $195

                                  Price per night from

                                  $195

                                  Details

                                  Distance approx 7.52 km from Winter Harbor

                                    39

                                    Bay View

                                    DownEast and Acadia Maine / Sorrento

                                    Sorrento house

                                    5 12 7 nights min

                                    • 5 bedrooms
                                    • sleeps 12
                                    • 7 nights min
                                    • Child Friendly
                                    • Pet Friendly
                                    • Private garden

                                    Price per night from

                                    $524

                                    Price per night from

                                    $524

                                    Details

                                    Distance approx 13.56 km from Winter Harbor

                                      26

                                      Alacrity

                                      Mount Desert Island / Southwest Harbor

                                      Southwest Harbor house

                                      4 8 7 nights min

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

                                      Price per night from

                                      $393

                                      Price per night from

                                      $393

                                      Details

                                      Distance approx 13.67 km from Winter Harbor

                                        10

                                        Quiet Oceanfront Home On Quiet Bay Near Acadia (Lamoine)

                                        DownEast and Acadia Maine / Lamoine

                                        Lamoine house

                                        3 6 7 nights min

                                        • 3 bedrooms
                                        • sleeps 6
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Child Friendly
                                        • Car not necessary

                                        Price per night from

                                        $401

                                        Price per night from

                                        $401

                                        Details

                                        Distance approx 5.2 km from Winter Harbor

                                        (7) Excellent 

                                          32

                                          Oceanfront Schoodic Peninsula Log Home - 3 Bedrooms, 2.5 Baths Air-Conditioned

                                          DownEast and Acadia Maine / Gouldsboro

                                          Gouldsboro house

                                          3 8 min stay varies

                                          • 3 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $229

                                          Responds fast!
                                          avg. 2 hours 6 minutes

                                          Price per night from

                                          $229

                                          Details

                                          Distance approx 13.88 km from Winter Harbor

                                          (6) Excellent 

                                            32

                                            Captain Nathan Clark House

                                            Mount Desert Island / Southwest Harbor

                                            Southwest Harbor house

                                            6 14 min stay varies

                                            • 6 bedrooms
                                            • sleeps 14
                                            • min stay varies
                                            • Nearest beach 2 mi
                                            • Child Friendly
                                            • Ask about pets
                                            “A wondeful week with friends and family in a charming, historica” We thoroughly enjoyed our week at the Nathan Clark House. The house sleeps 14 people which made it possible for us to enjoy the week with two other families. The house is across from th
                                            …see more

                                            Price per night from

                                            $516

                                            Price per night from

                                            $516

                                            Details

                                            Distance approx 13.83 km from Winter Harbor

                                              5

                                              Greendays

                                              Mount Desert Island / Southwest Harbor

                                              Southwest Harbor house

                                              4 7 7 nights min

                                              • 4 bedrooms
                                              • sleeps 7
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Child Friendly

                                              Price per night from

                                              $710

                                              Price per night from

                                              $710

                                              Details

                                              Distance approx 17.08 km from Winter Harbor

                                                24

                                                Loft Cabin w/Outdoor Patio-Near Acadia Nat'l Park!

                                                Mount Desert Island / Tremont

                                                Tremont log cabin

                                                1 5 min stay varies

                                                • 1 bedroom
                                                • sleeps 5
                                                • min stay varies
                                                • Child Friendly
                                                • Pet Friendly

                                                Price per night from

                                                $144

                                                Responds fast!
                                                avg. 29 minutes

                                                Price per night from

                                                $144

                                                Details

                                                Distance approx 6.08 km from Winter Harbor

                                                (41) Excellent 

                                                  19

                                                  Air Conditioned and Convenient

                                                  Mount Desert Island / Bar Harbor

                                                  Bar Harbor apartment

                                                  2 6 6 nights min

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • 6 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 0 mi
                                                  • Child Friendly
                                                  “Cozy home for a family” Thank you to DeeDee for making our stay in Bar Harbor a great one! I rented the house for my family and I, for a long weekend visit to Bar Harbor. My family made it to the house before I did, and DeeDee welcomed them and quick
                                                  …see more

                                                  Price per night from

                                                  $373

                                                  Price per night from

                                                  $373

                                                  Details

                                                  Distance approx 14.14 km from Winter Harbor

                                                    8

                                                    Harbor View apartment overlooking garden

                                                    Mount Desert Island / Southwest Harbor

                                                    Southwest Harbor apartment

                                                    1 4 5 nights min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 5 nights min
                                                    • Child Friendly

                                                    Price per night from

                                                    $258

                                                    Price per night from

                                                    $258

                                                    Details

                                                    Distance approx 13.29 km from Winter Harbor

                                                      25

                                                      Oceanfront Cottage w/ Dock & Mooring - walking distance to Acadia

                                                      Mount Desert Island / Southwest Harbor

                                                      Southwest Harbor cottage

                                                      4 8 7 nights min

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • 7 nights min
                                                      • Child Friendly
                                                      • Private garden

                                                      Price per night from

                                                      $573

                                                      Price per night from

                                                      $573

                                                      Details

                                                      Distance approx 12.3 km from Winter Harbor

                                                      (7) Excellent 

                                                        18

                                                        Hot Tub+AIR CONDITIONING+Fire Pit+Views & Access to Somes Sound-Near Acadia NP!

                                                        Mount Desert Island / Mount Desert

                                                        Mount Desert cottage

                                                        2 7 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 7
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 1 mi
                                                        • Child Friendly
                                                        “Absolutely fantastic!” We had a fantastic stay at The acadia. We were probably some of the first tourists of the season (mid april) and it was pretty chilly, so the hot tub was a very welcome amenity. The owners were wonderful, taking the time to sh
                                                        …see more

                                                        Price per night from

                                                        $139

                                                        Price per night from

                                                        $139

                                                        Details

                                                        Distance approx 14.9 km from Winter Harbor

                                                          13

                                                          "The Love Nest"

                                                          Mount Desert Island / Southwest Harbor

                                                          Southwest Harbor apartment

                                                          2 4 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 7 nights min
                                                          • Child Friendly
                                                          • Private garden

                                                          Price per night from

                                                          $258

                                                          Price per night from

                                                          $258

                                                          Details

                                                          Distance approx 16.52 km from Winter Harbor

                                                            11

                                                            Waterfront Front Home on Bass Harbor Tidal Bay

                                                            Tremont / Bass Harbor

                                                            Bass Harbor house

                                                            2 6 7 nights min

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

                                                            Price per night from

                                                            $474

                                                            Price per night from

                                                            $474

                                                            Details

                                                            Distance approx 9.95 km from Winter Harbor

                                                            (1) Excellent 

                                                              19

                                                              Haiku House - your gateway to Acadia

                                                              Mount Desert Island / Acadia National Park

                                                              Acadia National Park cottage

                                                              3 7 3 nights min

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

                                                              Price per night from

                                                              $544

                                                              Price per night from

                                                              $544

                                                              Details

                                                              Distance approx 3 km from Winter Harbor

                                                                24

                                                                Waterfront Prospect Harbor Cottage w/Yard&Fire Pit

                                                                Gouldsboro / Prospect Harbor

                                                                Prospect Harbor cottage

                                                                1 3 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 3
                                                                • 3 nights min
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $207

                                                                Responds fast!
                                                                avg. 3 hours 39 minutes

                                                                Price per night from

                                                                $207

                                                                Details

                                                                Distance approx 17.64 km from Winter Harbor

                                                                  36

                                                                  Quintessential Rustic Maine Oceanfront Cottage with Sunset Views

                                                                  Mount Desert Island / Tremont

                                                                  Tremont cottage

                                                                  2 7 7 nights min

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

                                                                  Price per night from

                                                                  $253

                                                                  Price per night from

                                                                  $253

                                                                  Details

                                                                  Distance approx 12.25 km from Winter Harbor

                                                                    21

                                                                    Deer Track, Cabin Overlooking Somes Sound

                                                                    Mount Desert Island / Mount Desert

                                                                    Mount Desert house

                                                                    1 4 7 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 7 nights min
                                                                    • Child Friendly
                                                                    • Private garden

                                                                    Price per night from

                                                                    $148

                                                                    Price per night from

                                                                    $148

                                                                    Details

                                                                    Distance approx 13.22 km from Winter Harbor

                                                                    (1) Excellent 

                                                                      13

                                                                      Merchants Cabin

                                                                      DownEast and Acadia Maine / Hancock

                                                                      Hancock house

                                                                      3 6 4 nights min

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

                                                                      Price per night from

                                                                      $247

                                                                      Price per night from

                                                                      $247

                                                                      Details

                                                                      Distance approx 6.13 km from Winter Harbor

                                                                      (9) Very Good 

                                                                        16

                                                                        Million Dollar View In Town, BOARDERS ACADIA (weekly rents park pass, Blue Pie)

                                                                        Mount Desert Island / Bar Harbor

                                                                        Bar Harbor house

                                                                        3 6 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 1 mi
                                                                        • Child Friendly
                                                                        “Fabulous Property” This was one of our first stops on our first ever visit to New England from the UK and we wish we could have stayed longer. Fabulous spacious property with wonderful views and so exciting for our daughter to see deer in the woods a
                                                                        …see more

                                                                        Price per night from

                                                                        $155

                                                                        Price per night from

                                                                        $155

                                                                        Details

                                                                        Distance approx 15.01 km from Winter Harbor

                                                                        (9) Very Good 

                                                                          29

                                                                          Deal-Cozy, 2B Home on wooded acre lot near by Acadia National Park/Lighthouse.

                                                                          Mount Desert Island / Acadia National Park

                                                                          Acadia National Park house

                                                                          2 5 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 5
                                                                          • min stay varies
                                                                          • Nearest beach 1 mi
                                                                          • Child Friendly
                                                                          • Private garden

                                                                          Price per night from

                                                                          $125

                                                                          Price per night from

                                                                          $125

                                                                          Details

                                                                          Distance approx 10.05 km from Winter Harbor

                                                                          (1) Excellent 

                                                                            11

                                                                            BlackBerry Cottage on Hancock Point near Acadia National Park

                                                                            DownEast and Acadia Maine / Hancock

                                                                            Hancock cottage

                                                                            3 7 3 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 7
                                                                            • 3 nights min
                                                                            • Nearest beach 6 mi
                                                                            • Child Friendly
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $126

                                                                            Price per night from

                                                                            $126

                                                                            Details

                                                                            Distance approx 8.17 km from Winter Harbor

                                                                            (2) Excellent 

                                                                              136

                                                                              ON the ocean panorama. Bar Harbor/Acadia. Peerless

                                                                              Mount Desert Island / Bar Harbor

                                                                              Bar Harbor house

                                                                              4 10 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $600

                                                                              Price per night from

                                                                              $600

                                                                              Details