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. Both children and adults love swimming in the ocean or exploring the beach for sea glass, sea creatures, rocks, and other treasures. Land’s End offering stunning ocean views along with the Land’s End Gift Shop is also just a short walk away.
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 has a full size bed, plus there is a daybed with trundle in the living room. The cottage is fully furnished except for bed linens and towels. Please, no smoking and no pets. High speed internet access and basic cable TV included.
Very clean cottage with all the amenities of home! The kitchen is well-equipped for cooking and baking and the pantry is well-stocked with paper products, household necessities and extra blankets. There are extra pillows in the bedroom and 2 closets with hangers. The cottage literature is up to date and offers a wide range of things to see and do. Access to a semi-private beach is just down the road! The proprietor was friendly and accommodating. We enjoyed our stay!
My husband and I had such a wonderful long weekend to kick off the summer at the cottage. There's no place like this. Joan and Adam were beyond wonderful as hosts - we can't wait to go back. <3
Great experience. We found the cottage warm and inviting and just as described. The picture of the exterior doesn't quite do it justice, as we found it to be much more charming close up than it appears in the photo. The owners went out of their way to make us feel welcome. Would highly recommend this reasonably priced, spotlessly clean home away from home to anyone wanting peaceful attractive surroundings a short walk from the beach and from the Lands End gift shop and a short ride to some mighty fine dining.
Had a great first time Maine vacation on Bailey Island.
Windward HO Cottage was clean and very tidy with a well equipped kitchen.
My partner and I enjoyed the 3 minute walk to Lands End to watch the beautiful sunrise, with coffee and blueberry muffins from Salt Cod and B.I.G.S general store. They also serve up some great breakfast food!
Loved the peace and serenity on the Island, but did venture out to Reid State Park and Brunswick for more site seeing
Picked up some fresh Lobsters from local fisherman and cooked back at the cottage with a propane cook top Joan provided.
Thank you Joan, we really enjoyed our stay!
Sincerly, Cathy and Jeff
Location, location, location...this rustic, cozy, and tidy cottage is in a great location on Bailey Island. You can walk 500 feet and be at Land's End beach, and be sure to go into the gift shop there for home made fudge, yummo! The owner of Windward Ho cottage, Joan is also nice enough to allow you to use the private beach in the back of her home, which is two houses down from the cottage. This private beach area has seats available, and the view is wonderful. The kitchen in this cottage is very well equipped for any type of cooking or baking you may want to do. Our daughter, is a Bowdoin student, and she even stayed with us there for a couple of nights, because the area is so special. The beds were comfortable, and overall, we had a really nice stay and vacation, I'd definitely come back here. Thank you Joan for sharing your cottage with us. The sunsets and the star gazing at night is incredible!
My boyfriend and I stayed at windward ho for our anniversary in September, and it couldn't have been more perfect. The location is ideal with a view of the water. There is also beach access a short walk away.
The cottage is well equipped with wifi, plenty of outlets, and everything you need in the kitchen. Although, it has plenty of modern amenities it also still has a rustic charm that is just want I wanted on a trip to Maine.
Joan was very helpful and nice. I definitely would love to come back for a longer stay next year!
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, 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 and Ale House at the North end of the Island.
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.