House in Bailey Island, ME
7 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Welcome to Whitesail's House!
Perched along the western shore of Bailey Island, Whitesail's House offers a front-row seat to some of the most breathtaking scenery in Midcoast Maine. From its peaceful perch near the end of the island, this elegant seaside cape captures golden sunsets over Harpswell Sound and even distant views of Mt. Washington on a clear day. With rocky shore frontage and a private water's-edge deck, this home brings the beauty of the Atlantic right to your doorstep. Watch the lobstermen glide in and out of Mackerel Cove, listen to the calming crash of the waves, and savor the salty breezes that drift across the property throughout the day.
Inside, Whitesail's House combines classic coastal charm with spacious comfort. The fully equipped kitchen invites you to prepare anything from a hearty breakfast to a fresh lobster dinner. Two dining rooms, each with their own unique character, provide space for intimate meals or lively gatherings. The formal living room, complete with a large flat-screen TV, offers a cozy place to unwind while still enjoying ocean views through the windows. Wherever you settle on the main level, the sea is never out of sight.
Also on the first floor are a full bathroom and a dedicated laundry room with washer and dryer, making longer stays easy and convenient.
Upstairs, the home opens to four beautifully arranged bedrooms, designed to welcome families and groups with comfort and privacy. In its own serene wing, the primary bedroom offers a king bed, sitting area, big-screen TV, and a private ensuite bathroom, all with shimmering water views that greet you each morning. The opposite wing of the home includes three additional bedrooms and one and a half bathrooms: a spacious bedroom with a king bed, a twin bedroom, and another twin bedroom with a trundle bed—perfect for kids or additional guests. An office is also located on this level, providing a quiet retreat for remote work, reading, or planning your next island adventure. High-speed wireless internet ensures you stay connected when needed.
Outdoor living is where Whitesail's truly shines. The covered porch invites peaceful morning coffee moments, shaded afternoon lounging, or rainy-day relaxation with the ocean as your backdrop. Steps away, the oceanside deck places you nearly at the waterline, an unforgettable setting for dining al fresco, stargazing, or simply soaking in the serene rhythm of the tides.
Whether you're gathering with family, vacationing with friends, or seeking a tranquil coastal retreat, Whitesail's House offers the ideal blend of spacious comfort, classic style, and unrivaled ocean scenery.
Come experience the magic of Bailey Island and make Whitesail's House your home by the sea.
Please note: Fireplace is not available for renter(s) use.
Perched along the western shore of Bailey Island, Whitesail's House offers a front-row seat to some of the most breathtaking scenery in Midcoast Maine. From its peaceful perch near the end of the island, this elegant seaside cape captures golden sunsets over Harpswell Sound and even distant views of Mt. Washington on a clear day. With rocky shore frontage and a private water's-edge deck, this home brings the beauty of the Atlantic right to your doorstep. Watch the lobstermen glide in and out of Mackerel Cove, listen to the calming crash of the waves, and savor the salty breezes that drift across the property throughout the day.
Inside, Whitesail's House combines classic coastal charm with spacious comfort. The fully equipped kitchen invites you to prepare anything from a hearty breakfast to a fresh lobster dinner. Two dining rooms, each with their own unique character, provide space for intimate meals or lively gatherings. The formal living room, complete with a large flat-screen TV, offers a cozy place to unwind while still enjoying ocean views through the windows. Wherever you settle on the main level, the sea is never out of sight.
Also on the first floor are a full bathroom and a dedicated laundry room with washer and dryer, making longer stays easy and convenient.
Upstairs, the home opens to four beautifully arranged bedrooms, designed to welcome families and groups with comfort and privacy. In its own serene wing, the primary bedroom offers a king bed, sitting area, big-screen TV, and a private ensuite bathroom, all with shimmering water views that greet you each morning. The opposite wing of the home includes three additional bedrooms and one and a half bathrooms: a spacious bedroom with a king bed, a twin bedroom, and another twin bedroom with a trundle bed—perfect for kids or additional guests. An office is also located on this level, providing a quiet retreat for remote work, reading, or planning your next island adventure. High-speed wireless internet ensures you stay connected when needed.
Outdoor living is where Whitesail's truly shines. The covered porch invites peaceful morning coffee moments, shaded afternoon lounging, or rainy-day relaxation with the ocean as your backdrop. Steps away, the oceanside deck places you nearly at the waterline, an unforgettable setting for dining al fresco, stargazing, or simply soaking in the serene rhythm of the tides.
Whether you're gathering with family, vacationing with friends, or seeking a tranquil coastal retreat, Whitesail's House offers the ideal blend of spacious comfort, classic style, and unrivaled ocean scenery.
Come experience the magic of Bailey Island and make Whitesail's House your home by the sea.
Please note: Fireplace is not available for renter(s) use.
Amenities at Situated at the waters edge with picturesque sunset views to Mt Washington.
Non-smoking
No pets allowed
Family friendly
Map of Bailey Island, ME
Ratings and reviews
10 / 10Outstanding·Jul 2026
From the very first glimpse of the ocean shimmering beyond the porch, we knew our stay on Bailey Island would be unforgettable. This breathtaking New England home felt like a fairytale. The house was beautifully maintained, extremely spacious, cozy, and full of charm, but the true highlight was the incredible front porch and sun deck.We spent hours every day outside—drinking coffee in the morning as lobster boats quietly rolled through the cove, watching the tide change, and ending each evening with a beverage and breathtaking sunsets. It was the perfect place to slow down and soak in everything that makes coastal Maine so special. My mom even joked that it looked like we were staying at the Kennedy residence when she FaceTimed her grandkids.Traveling with two young children can be a challenge, but this home made it effortless and joyful. Our son beamed as he ran from window to window shouting “OCEAN!”, and the spacious yard gave us all plenty of room to play, and grill dinner while soaking in the peaceful views.The location was wonderful, offering the peaceful charm of Bailey Island while still being close to everything we wanted to see and do. One of my favorite memories was when the tide rolled out, we would take our son to explore tide pools and find hermit crabs—moments we’ll never forget.We left already talking about when we can come back—not just to Bailey Island, but to this special home.
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Top rated by guests
10Outstanding
(1 Rating)
"From the very first glimpse of the ocean shimmering beyond the porch, we knew our stay on Bailey Island would be unforgettable. This breathtaking New England home felt like a fairytale. The house was ..."
Rosie F.Don't miss out! Price and availability may change
