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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Small Cottage With Beach Access

Bedrooms 1
Space 400 sq. ft.
Property type cottage
Minimum Stay 3 - 7 nights


About the property

One Bedroom Rustic Cottage

Windward Ho is a small, clean, rustic cottage on beautiful Bailey Island. Experience the wonders of a Maine Island that is only a 15 minute drive from Brunswick with it's professional Maine State Theater, 20 minutes from Freeport with the 24 hour shopping experience of LL Bean's and 1 hour from the city experience of Portland.

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.

More Details

Property Manager
Carl Johnson and Leslie Lampert
Member since: 2014
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
June 26, 2017


Bailey Island Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 400 sq. ft.
House Rules:
  • Max. occupancy: 3
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Ocean View ...
  • Rural
  • Away From It All
  • Budget
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Living Room ...
  • Parking ...
  • Coffee Maker
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • Bathroom 1 - toilet , shower
  • Guests provide their own towels.
  • 1 Bedroom, Sleeps 3
  • Bedroom 1 - 1 double
  • The bedroom has a full size bed. The living room has a built in twin size bed with another twin bed that pulls out. Guests provide their own linens for the beds. Blankets and pillows are provided.
  • Books
  • Satellite / Cable ...
  • Television
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill ...
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • library
  • live theater
  • marina
  • museums
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • groceries
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • swimming
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.


Excellent! 4.5/5 -
(6 traveler reviews)

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Small Cottage With Beach Access
average rating of 4.5 based on 6 reviews
Syracuse NY

Great Place For A Getaway!

  • 4 of 5

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!

  • Submitted: Jun 28, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
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1 0
Arlington, MA

What a beautiful stay!

  • 5 of 5

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

  • Submitted: Aug 18, 2015
  • Stayed: May 2015
  • Source: HomeAway
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1 0

Windward Ho is definitely a keeper

  • 5 of 5

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.

  • Submitted: Aug 16, 2015
  • Stayed: Aug 2015
  • Source: HomeAway
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1 0

Quiet, Quaint Get Away

  • 4 of 5

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

  • Submitted: Aug 14, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
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1 0

Perfect Location!!!

  • 4 of 5

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!

  • Submitted: Jun 21, 2015
  • Stayed: Jun 2015
  • Source: HomeAway
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2 0
New York, NY

Rustic charm on Baily Island

  • 5 of 5

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!

  • Submitted: Sep 30, 2014
  • Stayed: Sep 2014
  • Source: HomeAway
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7 0


Bailey Island Cribstone Bridge
"One of only 2 Cribstone Bridges in America."
Cook's Lobster House
"Wonderful place to enjoy fresh sea food on the island"
Maine State Music Theater
"Professional theater all summer long!"
LL Bean Outdoor Discovery Schools
"Enjoy 24 hour shopping, outdoor concerts and the outdoor discovery school"
Nearest Airport
46 Miles
Portland International Jet Port
Nearest Barpub
2 Miles
Morse's Cribstone Grill
Nearest Ferry
2 Miles
Casco Bay Ferry Lines
Nearest Golf
11 Miles
Mere Creek Golf Course, Brunswick
Nearest Train
15 Miles
Brunswick Station-Downeaster
Nearest Motorway
13 Miles
Route 1 to I-295
Nearest Restaurant
1.5 Miles
Giant Stairs Seafood Grille
Nearest Beach
0.25 Miles
Little Harbor
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, 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 and Ale House at the North end of the Island.


Rates & Availability

Bailey Island Cottage Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Jun 17 2017 - Sep 8 2017
Changeover Day: Saturday
7 night minimum stay
Sep 9 2017 - Oct 24 2017
3 night minimum stay

Additional information about rental rates

CCProcessing $25
Tax Rate 9.0%

Cash rates are available upon inquiry.

Manager's Cancellation Policy

  • 50% refund if canceled at least 7 days before arrival date.
  • 100% refund if canceled at least 14 days before arrival date.
Contact Manager