| | Name | Town | Br | Sleeps | Weekly | |
 Well-maintained Cape Cod style house with Easterly views of Harpswell Sound.
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| Adams |
Harpswell
| 4 | 8 |
$1950
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 3 season cottage with gorgeous sunset views. Within walking distance to most places on Bailey Island.
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| Addison Red |
Bailey Island
| 2 | 5 |
$800
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 Ocean view, great yard for kids, and a short walk to Cedar beach!
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| Anchorage |
Bailey Island
| 3 | 6 |
$800
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 Charming two story cottage on Lowell's Cove.
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| Barnacle |
Orr's Island
| 2 | 6 |
$1600
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 Private location with several decks, sunset views, and private dock.
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| Bolton's Hideaway |
Great Island
| 5 | 8 |
$2100
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 Perfect location within walking distance to Cedar Beach.
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| Briny Junior |
Bailey Island
| 1 | 2 |
$500
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 The views are just beautiful, facing west with the sunsets over Harpswell Sound.
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| Broad View |
Bailey Island
| 4 | 6 |
$1650
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 Deep waterfront, kid-friendly home with beautiful sunset views!
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| Buoy Ledges |
Bailey Island
| 3 | 8 |
$1950
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 Perfect for a small family or couple, enjoy a large yard, water access and sunset views.
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| Camp Bullwinkle |
Harpswell
| 3 | 6 |
$1700
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 Spoil yourself with this high-end home located directly on Deep waterfront.
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| Camp Run-a-Muck |
Great Island
| 5 | 8 |
$3500
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 Spacious home perfect for a large family or group of friends. Located on Quahog Bay, private location.
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| Cedar Ledge |
Cundy's Harbor
| 5 | 10 |
$3100
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 Privately located with Easterly views down Gun Point Cove! Enjoy the shade by the house, or sun on the Dock!
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| Chamberlain |
Orr's Island
| 2 | 5 |
$1200
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 Perfect location for swimming, boating, and fishing! Pingpong in the Basement!
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| Cordovano |
Great Island
| 3 | 6 |
$1950
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 This classic Maine cottage is a favorite! Great Living space, wonderful waterfront location on beautiful Mackerel Cove!
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| Crow's Nest |
Bailey Island
| 3 | 6 |
$1800
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 This Charming waterfront cottage has nice decks, and its own dock.
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| Dominic's |
Orr's Island
| 3 | 5 |
$1500
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 Enjoy the crashing surf from the deck of this garage apartment.
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| Edgecliff |
Bailey Island
| 1 | 3 |
$1000
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 4 Season Oceanfront Home with spectacular sunrises, beautiful Bold Ocean views!
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| Eider Ledge |
Bailey Island
| 4 | 7 |
$2000
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 Beautiful sunsets with tidal waterfront. A great rental for a small family.
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| Eleazer |
Bailey Island
| 3 | 6 |
$1350
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 Beautiful sunrises at this Private Oceanfront, beautifully decorated home. Lots of livings spaces, and great sun light!
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| Faulkner |
Orr's Island
| 4 | 8 |
$2900
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 This Post and Beam Home has a Private dock with Southwesterly views, and a large deck.
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| Genimatas |
Great Island
| 3 | 6 |
$1900
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 Beautiful sunsets from this upstairs studio apartment. Great affordable getaway for a couple.
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| Goldsmith Apartment |
Bailey Island
| 0 | 2 |
$450
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 Year round home with frontage on the Harpswell sound. Spectacular westerly views. Gas fireplace!
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| Goldsmith House |
Bailey Island
| 3 | 6 |
$1850
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 Charming cottage has a large deck that overlooks Mackerel Cove!
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| Grey Cottage |
Bailey Island
| 2 | 4 |
$875
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 Enjoy the crashing surf and overview of Little Harbor at this charming cottage.
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| Grey Rocks |
Bailey Island
| 5 | 6 |
$1375
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 Cottage sits one lot back from the Ocean creating a serene location with beautiful Ocean views.
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| Hamann |
Bailey Island
| 3 | 6 |
$950
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 Unique Colonial with right of way to rocky beach at Little Harbor. Limited View of Mackerel Cove!
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| Hay |
Bailey Island
| 3 | 6 |
$975
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 Wake up and enjoy your favorite morning beverage outside on the balcony or down on the expansive dock as the sun rises from the east. Enjoy spectacular views of the bay.
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| High View |
Great Island
| 2 | 6 |
$1950
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 Breathtaking sunrises, and just a short walk to Cedar beach at this beautiful Private year round home.
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| Howard's End |
Bailey Island
| 3 | 10 |
$3500
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 This 19th century stone and shingle cottage has Eastern and Western views of the Ocean.
Relax on the swing from the porch or enjoy lunch on the either of the two open decks.
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| Inner Ledge |
Bailey Island
| 4 | 7 |
$3500
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 Perfect getaway for a couple or a vacation by yourself. Hear the waves as they crash on the rocks right in front!
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| Jaquish North |
Bailey Island
| 1 | 2 |
$850
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 Perfect getaway for a couple or a vacation by yourself. Hear the sounds of crashing surf right out front!
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| Jaquish South |
Bailey Island
| 1 | 2 |
$850
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 Year 'round house with a nice deck and gorgeous sunset views. A great quite neighborhood, right of way stairs to the rocky shore front!
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| Kals |
Bailey Island
| 3 | 6 |
$1350
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 Cottage has a beautiful sunset view, and a nice yard, also has a shared dock, and pebbly beach.
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| Kelley Cottage |
Orr's Island
| 2 | 4 |
$900
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 Spectacular views of Little Harbor from the covered porch of cottage. Right of way to pebbly beach at Little Harbor!
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| Lee |
Bailey Island
| 3 | 6 |
$1375
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 This pleasant year 'round cape is centrally located with a limited view of the Bay. Easy walk to water.
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| Lord |
Bailey Island
| 3 | 6 |
$925
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 This cute two story cottage has beautiful sunsets and a glassed in porch. There are steps that lead down to a rocky shore front.
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| McCollum |
Bailey Island
| 2 | 5 |
$975
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 A one story home with beautiful Ocean views from the front of the cottage, and nice sunsets views from the back deck!
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| McDonnell |
Great Island
| 3 | 5 |
$950
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 Simple, cute, and sunny at this house. Spectacular sunrises from the East side of the Island. A wrap around deck, with table and umbrella!
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| Mingo Cove |
Bailey Island
| 2 | 5 |
$1100
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 Water views from every room of this beautiful year round home. Two beautiful stone fireplaces, granite counter tops, and a large deck with a outside shower!
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| Morning Glory |
Great Island
| 4 | 8 |
$2500
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 Ranch style house with a big yard,large porch, sunset views, and right of way with steps to shore which is about 125 yards from the cottage!
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| Pablito |
Orr's Island
| 3 | 6 |
$900
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 A very cute and cozy cottage. Centrally located on the Island at the end of Steamboat Road. Shared pebbly beachfront sits just steps from the deck, beautiful westerly sunset views.
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| Parciak Cottage |
Bailey Island
| 1 | 2 |
$775
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 This lovely new home is spacious, sunny, and comes with all the comforts of home. The home even has two master suites on the first floor, along with 2 gas fireplaces, 2 living rooms, a nice screened in porch, and multiple decks!
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| Parciak House |
Bailey Island
| 4 | 8 |
$3100
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 This one story cottage is very sunny. There are 2 decks, a nice yard, with a swingset for the kids, and spectacular sunset views.
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| Ragsdale |
Bailey Island
| 2 | 6 |
$1300
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 Enjoy a water front deck at the dock. If you enjoy the shade, or you like to sun, this is the place. Swim from the dock, or just sit and watch the lobstermen haul their traps. Seals play on the surrounding ledges. Quiet,peaceful and with a sunset view to boot!
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| Sanctuary |
Great Island
| 5 | 8 |
$2600
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 This very sunny two story, year round house has great Ocean front. Enjoy the beautiful ocean views, wonderful sunrises and the rocky beach area right off the deck.
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| Saranole |
Great Island
| 4 | 8 |
$1900
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 This quaint cottage has a great central location, with easy access to crashing surf by the Giant Staircase!
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| Satterthwaite |
Bailey Island
| 4 | 7 |
$950
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 Beautiful views,and frontage on Mackerel Cove. Watch the lobstermen at work from the deck. Swim and fish from your own private dock! The water actually goes right under the large deck at high tide!
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| The Lodge |
Bailey Island
| 2 | 4 |
$1400
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 Charming Ranch is great for fishing and swimming. Sit on the east facing porch and watch the lobstermen haul traps, or watch as the beautiful Yachts sail by on their way to the Great Island Boat Yard just up the way!
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| The Narrows |
Great Island
| 2 | 4 |
$1275
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 This sweet cottage sits on Tip-Tops hillside with views of Mackerel Cove & the Bay. One story year-round home is sunny, cozy and has a nice deck with beautiful sunset views.
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| The Studio |
Bailey Island
| 2 | 4 |
$875
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 This a cozy Log Cabin is located on beautiful Mackerel Cove. The view is very limited! The cabin is surrounded by tree's, but there is a path leading down to the water!
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| Tip- Top Log Cabin |
Bailey Island
| 2 | 4 |
$775
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 This charming cape is centrally located in the heart of Bailey Island with a grassy fenced in yard. Beautiful sunset views over Mackerel Cove & Lowell's Cove. These are the most photographed coves in the area. Town access to the water at the cove. This property also has Beautifully maintained flower gardens a large yard, and even a swingset for the kids!
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| Two Coves |
Bailey Island
| 3 | 8 |
$1775
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 This Year round home is only 6 miles to Brunswick. Enjoy this quiet location, with lovely sunrises!
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| Valhalla |
Great Island
| 2 | 4 |
$1500
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 This charming cottage is located in a great neighborhood in the Lowells Cove area. Cottage has a nice yard with swimming close by at rocky cove area. There is a limited view of the water from the house. The rocky swimming area has long southeast views down the cove.
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| Whalewatch |
Orr's Island
| 3 | 6 |
$975
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 Great location almost to the end of the island. Beautiful deck with south west ocean views, and incredible sunsets. Rocky shore front access.
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| Whitesails Cottage |
Bailey Island
| 1 | 2 |
$700
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 This lovely cape has a nice yard, beautiful sunset views, with a rocky shore front.
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| Whitesails House |
Bailey Island
| 4 | 6 |
$2400
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 This 1860 Cape has been renovated, nicely furnished, & has the most beautiful panoramic Ocean view on the Island.
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| Windy Hill |
Bailey Island
| 2 | 8 |
$1700
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