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Small Cottage With Beach Access

Bailey Island, Harpswell, ME, USA
  • Cottage750 sqft
  • Bedrooms1
  • Sleeps3
  • Bathrooms1
  • Half Baths0
  • Minimum Stay3 - 7 nights

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.


Carl Johnson and Leslie Lampert

Member Since 2014
Premier Partner
This HomeAway partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.
Response rate:
Response time:
within one hour
Calendar last updated:
Apr 19, 2018


    • Internet
    • Heater
    • Satellite or Cable
    • Kids Welcome
    • Parking
    • TV
    • No Smoking


      • 1 Bedrooms, 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.


      • 1 Bathroom
      • Bathroom 1
        toilet, shower
      • Guests provide their own towels.

      Location Type

        • Ocean View
          Westerly view of Casco Bay with breathtaking sunsets.
        • Rural


            • Away From It All
            • Budget


                • Guests provide their own meals


                    • Hair Dryer
                    • Heating
                      A propane heater provides warmth for a chilly morning or evening.
                    • Internet
                      Wireless internet provided
                    • Living Room
                      A daybed and trundle located in the living room provide sleeping for 2 additional guests and require twin size bedding .
                    • Parking
                      Guests park on the lawn parallel to the building.


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


                            • Dining Area
                            • comfy seating for 4 people


                                • Books
                                • Satellite / Cable
                                  Basic cable TV
                                • Television


                                    • Deck / Patio
                                    • Lawn / Garden
                                    • Outdoor Grill
                                      Lobster cooker also available upon request.


                                        • 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

                                                        • pier fishing
                                                        • cycling
                                                        • fishing
                                                        • golf
                                                        • hiking
                                                        • deepsea 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.

                                                              House Rules

                                                              Check-in: 3:00 PM

                                                              Check-out: 11:00 AM

                                                              Cancellation Policy

                                                              100% refund if canceled at least 14 days before arrival date. 50% refund if canceled at least 7 days before arrival date. You must contact the owner directly to request cancellation.

                                                              13 Reviews


                                                              Latest reviews

                                                              Rustic and close to the water

                                                              Matt C.Harrisburg, PA

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

                                                              Re- Connected

                                                              Kenyon F.

                                                              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!

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

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

                                                              New England Charm Perfection!

                                                              nancy m.

                                                              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!

                                                              Very clean & quiet

                                                              Alan M.Rochester, NH

                                                              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.

                                                              Loved this place!

                                                              Rosaleen H.

                                                              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.


                                                              Bailey Island, Harpswell, ME, USA

                                                              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

                                                              Additional information about rental rates

                                                              Cleaning Fee
                                                              Tax Rate

                                                              Cash rates are available upon inquiry.

                                                              13 Reviews
                                                              Excellent 4.7/5
                                                              Premier Partner
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                                                              For booking assistance, call 888-640-7927

                                                              Property # 3697949