Home Vacation Rentals By Owner In Bailey Island, ME

Showing 43 Of 43 Vacation Rentals
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Exceptional(27)

$408.75

/ Nightly
Cottage

Wake to Sunrise on the Ocean

Bailey Island, Maine, United States

Enjoy all three seasons, Spring Summer and the quiet of Fall. Central heat and fireplace will keep you toasty in this traditional 1891shingle-style cottage sitting on a bluff with ocean views from every room. This will make you feel like you are stepping back in time to the way things used to be. brbrSleep with the sound of the surf. Wake up to the sunrise and enjoy breakfast on the large front porch. Nothing to see but water, islands and boats, both working and sail. Back for the night, cook up some lobster from local fisherman, enjoy the meal in the fully appointed dining room (lobster bibs included) enjoy the sunset over Mt Washington and come in from the cool night air to read by the fire in the fireplace. Enjoy games of scrabble or cards, enjoy the challenge of a jigsaw puzzle. Then back to bed to the sound of the surf. It's a good day on Bailey Island.
Bed 4

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Bath 2

Bath

Sleep 7

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Exceptional(11)

$392.0

/ Nightly
Cottage

Turn-of-the-Century Classic Maine Cottage with Sweeping Southeasterly Ocean Views

Bailey Island, Maine, United States

Welcome to Spindrift!brbrExperience the quintessential Maine coastal getaway at Spindrift, a turn-of-the-century New England-style cottage perched right on the water's edge at the mouth of Little Harbor. With sweeping southeasterly ocean views, the rhythmic sound of waves crashing against nearby ledges sets the tone for a truly relaxing retreat. This charming cottage is the perfect spot to savor sunsets over the Atlantic while feeling completely immersed in the natural beauty of Maine's rugged coastline.brbrStep onto the side deck or into the spacious sun porch, where outdoor living is brought inside with comfortable seating and a dining table, ideal for morning coffee, casual meals, or an evening cocktail while taking in the panoramic views. Enter through the back to discover a well-equipped laundry room with a large washer and dryer for added convenience.brbrAs you move through the home, you'll find a quaint sitting room with cozy chairs and a TV, perfect for relaxing after a day by the water. The kitchen, though compact, is thoughtfully designed and includes a small table and chairs, making it easy to prepare meals while staying connected with your guests.br​​​​​​​brThe heart of the home is the bright and airy living area, boasting 180-degree open ocean views and plenty of space to gather with family or friends. Large windows and thoughtful layouts make it easy to watch the tides, the lobster boats, or the ever-changing light across the water.brbrUpstairs, the cottage offers four spacious bedrooms and a full bathroom with a tub/shower combination. Sleep soundly in comfort with a variety of beds to suit your group:brKing-size bedroom with stunning ocean viewsbrQueen-size bedroom also offering beautiful water vistasbrFull-size bedroombrTwo twin beds in a cozy fourth bedroombrWake up to the sunrise over the Atlantic or enjoy the evening's golden light without even leaving your bed in the front bedrooms.brbrSpindrift combines timeless Maine charm with modern convenience, including laundry facilities and the owners' water bottle service for your comfort. Relax, recharge, and step back in time while embracing all the pleasures of coastal life.brbrPlease note: This property rents Saturday-Saturday in summer. Fireplace is available for renter(s) use.
Bed 4

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Bath 2

Bath

Sleep 8

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$915.89

/ Nightly
Private Vacation Home

Situated at the waters edge with picturesque sunset views to Mt Washington.

Bailey Island, Maine, United States

Welcome to Whitesail's House!brbrPerched 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.brbrInside, 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.brAlso on the first floor are a full bathroom and a dedicated laundry room with washer and dryer, making longer stays easy and convenient.brbrUpstairs, 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.brbrOutdoor 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.brbrWhether 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.brbrCome experience the magic of Bailey Island and make Whitesail's House your home by the sea.brbrPlease note: Fireplace is not available for renter(s) use.
Bed 4

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Bath 3

Bath

Sleep 7

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Home Most popular vacation rentals in Bailey Island

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$1379.94

/ Nightly
Cottage

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Bailey Island, Maine, United States

Bed 5

Bed

Bath 4

Bath

Sleep 12

Sleeps
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$270.87

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Cottage

Charming 4 bedroom Classic Maine Cottage located near the giant stairs.

Bailey Island, Maine, United States

Bed 4

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Bath 1

Bath

Sleep 7

Sleeps
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$314.82

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Private vacation home

Great Location! Expansive deck with huge yard! Well maintained path to the rocky shoreline.

Bailey Island, Maine, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

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$431.69

/ Nightly
Apartment

This spacious 2nd floor garage apartment offers phenomenal open ocean views!

Bailey Island, Maine, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

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$434.91

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Cottage

1890 Summer Cottage on an Ocean Bluff

Bailey Island, Maine, United States

Bed 5

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Bath 2

Bath

Sleep 8

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$487.72

/ Nightly
Private vacation home

The Beach Rose - 3BR, 2BA home perched overlooking picturesque Mackerel Cove

Bailey Island, Maine, United States

Bed 3

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Bath 2

Bath

Sleep 7

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$558.44

/ Nightly
Private vacation home

Enjoy spectacular sunset and water views from the deck and balconies with water access.

Bailey Island, Maine, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$491.72

/ Nightly
Private vacation home

This spacious home offers a FANTASTIC covered porch, perfect to spend your days gazing at the ocean!

Bailey Island, Maine, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

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$817.91

/ Nightly
Private vacation home

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

Bailey Island, Maine, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$650.30

/ Nightly
Private vacation home

Perched on the rugged cliffs of beautiful Bailey Island.

Bailey Island, Maine, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

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