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Small Cottage with Beach Access

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Windward Ho Cottage (occupancy upper level only)


Last updated: 09/14/2014
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:3-7 nights
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

Bailey Island cottage description

Windward Ho is a small, clean, rustic cottage on beautiful Bailey Island. This is an ideal getaway destination for relaxation and enjoyment of the Island’s natural beauty. From your westerly facing deck, the sunsets are breathtaking. Within a 5 minute walk, you will find Little Harbor our own semi private pebbly beach, or Land’s End offering stunning ocean views along with the Land’s End Gift Shop. If you’re an ice cream lover, you’ll find Tiffins Ice Cream close by.
The cottage is located high on a ledge with a distant view of Casco Bay. Rental unit is upper level only, no occupancy in lower level. One bedroom with full size bed, plus a daybed with trundle is in the living room. The cottage is fully furnished except for bed linens and towels. Please, no smoking and no pets. Internet access/basic cable TV available.

Property Type

  • Cottage
  • 400 sq. ft.

Accommodation Type

      • Vacation Rental


          • Guests Provide Their Own Meals


          • Children Welcome
          • Non Smoking Only
          • Wheelchair Inaccessible
          • Pets Not Allowed
          • Long-Term Renters Welcome

          Bedrooms: 1 Bedroom, Sleeps 2, Beds for 2

          • Bedroom 1: 1 double


          • Guests provide their own linens for a full size bed. Blankets and pillows provided. ...moreless

          Bathrooms: 1 Bathroom

          • Bathroom 1: toilet, shower


          • Guests provide their own towels.

          Other Amenities

              • Windward Ho is part of a family complex that was originally settled on by this family in the late 1700's. Since the beginning, we have had strong roots involving the commercial fishing industry and today as you move around the grounds you will find evidence of our continuing participation in the lobstering industry . A pile of neatly stacked traps waiting to be set or buoys waiting to be painted is all part of the aura within our family setting....moreless


              • Television
              • Books


              • Away From It All
              • Budget


              • Bay/Sound
              • Churches
              • Library
              • Marina
              • Restaurants
              • Autumn Foliage

              Leisure Activities

              • Antiquing
              • Beachcombing
              • Bird Watching
              • Photography
              • Scenic Drives
              • Sight Seeing
              • Walking

              local services and businesses

                  • Groceries

                  Location Type

                  • Rural
                  • Ocean View:

                    Westerly view of Casco Bay with breathtaking sunsets....moreless

                  sports and adventure activities

                  • Cycling
                  • Deepsea Fishing
                  • Fishing
                  • Golf
                  • Hiking
                  • Pier Fishing
                  • Sailing
                  • Scuba Diving Or Snorkeling
                  • Snorkeling
                  • Sound/Bay Fishing
                  • Swimming

                  catering options

                      • Guests Provide Their Own Meals


                      • Dining Area
                      • Seating for 4 people


                      • Heating
                      • Parking
                      • Internet:

                        Wireless internet provided...moreless

                      • Living Room:

                        A daybed and trundle located in the living room provide sleeping for 2 additional guests and require twin size bedding . ...moreless


                      • Kitchen
                      • Refrigerator
                      • Stove
                      • Oven
                      • Microwave
                      • Dishes & Utensils
                      • Coffee Maker
                      • Toaster


                      • Outdoor Grill:

                        Lobster cooker also available upon request....moreless

                      • Deck / Patio
                      • Lawn / Garden


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                      Rental basis: Per property
                      Dates Nightly Weekend Night Weekly Monthly * Event
                      Sep 6 - Oct 14, 2014
                      3 night min stay

                      Additional information about rental rates


                      • Tax Rate 8%


                      A nonrefundable deposit of half the rental fee is required to hold a reservation and the balance is due upon arrival. Deposits are refundable only if the reserved time can be rebooked. Payment is made by cashier's check, personal check, or cash. For further information contact owner.

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                      Last updated: 09/14/2014
                      Check availability
                      23 Available
                      21 Unavailable
                      22 Today
                      23 Selected dates


                      46 Miles
                      Nearest Airport
                      Portland International Jet Port
                      2 Miles
                      Nearest Ferry
                      Casco Bay Ferry Lines
                      15 Miles
                      Nearest Train
                      Brunswick Station-Downeaster
                      13 Miles
                      Nearest Motorway
                      Route 1 to I-295
                      0.25 Miles
                      Nearest Beach
                      Little Harbor
                      2 Miles
                      Nearest Barpub
                      Morse's Cribstone Grill
                      11 Miles
                      Nearest Golf
                      Mere Creek Golf Course, Brunswick
                      1.5 Miles
                      Nearest Restaurant
                      Giant Stairs Seafood Grille

                      Car: Necessary

                      Bailey Island is the outer most in a series of 3 picturesque islands that form a peninsula into the open Atlantic Ocean. These islands are connected to the mainland by three bridges, the last of which is the one of a kind 'Cribstone Bridge'. It is about a thirty minute drive from the Route One / Cook's Corner interchange in Brunswick. Please note that there is no fuel available after leaving the Brunswick area and heading out toward Bailey Island. People considering a stay here, may wish to note the following: Within the Brunswick / Bath / Topsham area you will find grocery stores, shopping malls, a cinema, national chain and numerous local restaurants. Also you will find retail outlets, fitness centers, medical facilities (including 2 hospitals), golf courses, The Bath Maritime Museum, and the Maine State Music Theater on the Bowdoin College campus. Freeport is about a forty-five minute drive and you will find the flagship stores and campus of LL Bean along with many unique outlet stores. In essence, while enjoying the natural beauty of Bailey Island, the region offers an array of sights, activities, and resources for our guests.

                      Other Activities:

                      local art shows and galleries

                      Land's End Gift Shop

                      H2O Outfitters for kayaking

                      Casco Bay Lines Nature Cruise departs everyday ( June thru August) at noon from Cooks lobster house at the North end of the Island


                      Owner info

                      Contact us

                      Speaks: english



                      • Windward Ho Cottage (occupancy upper level only)

                        Windward Ho Cottage (occupancy upper level only)

                      • Living room

                        Living room

                      • Kitchen/Dining Area

                        Kitchen/Dining Area

                      • Bedroom with full size bed

                        Bedroom with full size bed

                      • Little Harbor with pebbly beach

                        Little Harbor with pebbly beach

                      • Mackerel Cove

                        Mackerel Cove

                      • Sunrise at Little Harbor

                        Sunrise at Little Harbor

                      • Living room

                        Living room

                      • Daybed in living room

                        Daybed in living room

                      • Kitchen


                      • Deck


                      • Little Harbor,a small semi private beach, a short walk from Windward Ho

                        Little Harbor,a small semi private beach, a short walk from Windward Ho

                      • Mackerel Cove

                        Mackerel Cove

                      $110 per night (USD)

                      1 Bedroom / 1 Bathroom
                      Sleeps 2

                      View calendar: Updated 09/14/14
                      Minimum stay: 3-7 nights
                      Dates are unavailable
                      Please stay a bit longer. A stay of nights or more is required for these dates.
                      This listing requires that rentals start on a .
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                      Email owner

                      +1 2078332987
                      Please no calls after 9:00 PM EST

                      Speaks: english
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                      Small Cottage With Beach Access

                      Bailey Island #3697949ha

                      1 BR  1 BA  Sleeps 2

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