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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 750 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

Carl Johnson and Leslie Lampert
Member since: 2014
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
March 22, 2018


Bailey Island Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 750 sq. ft.
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 3
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
  • There will be a $25 per person/per night fee charged for overnight guests who are not part of the original booking, 48 hrs advanced notice required.
  • No pets allowed on the property, even if they are being kept outdoors. (IE: No outside cages.)
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! 4.7/5 -
(13 traveler reviews)

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Small Cottage With Beach Access
average rating of 4.6923075 based on 13 reviews
Harrisburg, PA

Rustic and close to the water

  • 5 of 5

Carl was great- we were able to relax and enjoy our surroundings (especially the Giant's Stairs, Mackerel Cove, and Land's End).

  • Submitted: Oct 18, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Re- Connected

  • 5 of 5

The stay at "Windward Ho" was incredible! Absolutely love this place!

Reconnected with my childhood memories. The Johnsons have all the little details that we would forget, totally covered. Thank you so much!

  • Submitted: Oct 3, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
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Great stay as always... Off of the beaten path, no crowds of tourists.

  • 5 of 5

Great stay as always... Off of the beaten path, no crowds of tourists.

  • Submitted: Sep 1, 2017
  • Stayed: August 2017
  • Source: HomeAway
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New England Charm Perfection!

  • 5 of 5

This house! What a perfect week! You simply can't beat it for twice the price. We were in town for the

Bowdoin Music Festival in Brunswick, about a 25 minute drive. Don't let the pictures fool you. I was a bit trepidatious seeing the pics online, but owners we kind enough to let me walk through the cottage the week before and all my worries floated away. It is spotless! Like really really clean. Not a cobweb in sight. There is a lovely welcoming deck perfect for reading or having a glass of wine while watching the sunset. The Home is quite well appointed. China service for 4 with lots of pots and pans. Large fridge and stove/oven so we made our own breakfast and lunch and a couple of dinners. The trundle bed was comfortable as was the full bed in the bedroom. Bring your own sheets and towels. There were coffee filters and a maker. There's a very effective heater for those chilly nights. Wifi was good. It was so quiet at night. Easy short walk to lovely cove beach as well as Land's End gift shop and another small beach. Owners Carl and Lesley were wonderful. Very responsive. Let us check in a bit early. They truly care about their guests' satisfaction. A terrific value on Bailey Island!

  • Submitted: Jul 18, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
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Rochester, NH

Very clean & quiet

  • 5 of 5

Immaculate and well stocked with basics. Nice deck to sit and grill. Very relaxing and enjoyable spot. A bit small but space used very efficiently. Owners are exceptional. Were there to greet us and answer any questions. Made us feel at home the entire week. Would definitely return on our next trip to Bailey Island. Thank you Carl & Leslie for your hospitality.

  • Submitted: Jul 10, 2017
  • Stayed: June 2017
  • Source: VRBO, from HomeAway
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Loved this place!

  • 5 of 5

So, this cottage is rustic, but so sweet.

It is immaculate, and clean, and comfortable.

We love Bailey Island and were lucky to stay before the season really started because the island was not crowded.

This was a wonderful get-a-way! Thank you.

  • Submitted: Jun 29, 2017
  • Stayed: June 2017
  • Source: HomeAway
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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

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $75

Cash rates are available upon inquiry.

Owner'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.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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