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