| | Name | Town | Br | Sleeps | Weekly | |
 Beautiful sunset views over Mackerel Cove & Lowell's Cove and just a short walk to the water.
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| 2 Coves |
Bailey Island
| 3 | 8 |
$1850
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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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| A Point of View |
Bailey Island
| 2 | 8 |
$1500
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 Well-maintained Cape Cod style house on the waters edge, with Easterly views of Harpswell Sound.
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| Adams |
Harpswell
| 4 | 8 |
$1950
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 This 3 season cottage is located right on the water, and has gorgeous sunset views. Within walking distance to most places on Bailey Island. Large deck overlooking the bay, nice quiet side street location.
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| Addison Red |
Bailey Island
| 2 | 5 |
$825
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 Limited Ocean view, great yard for kids, and a short walk to the beach (right of way) at the end of the street.
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| Anchorage |
Bailey Island
| 3 | 6 |
$800
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 Charming, two story, classic Maine cottage on Lowell's Cove. Steps to pebbly beach, a perfect spot for kayaking!
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| Barnacle |
Orr's Island
| 3 | 6 |
$1650
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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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| Berkshire |
Great Island
| 3 | 5 |
$975
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 This classic Maine cottage sits at the water's edge with a great yard and has steps leading down to the waterfront.
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| Blair Cottage |
Harpswell
| 4 | 7 |
$950
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 A Private waterfront location with several decks, sunset views, and private dock. Perfect place for a family!
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| Bolton's Hideaway |
Great Island
| 5 | 8 |
$2200
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 Perfect location within walking distance to Cedar Beach.
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| Briny Junior |
Bailey Island
| 1 | 2 |
$525
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 Beautiful sunset views over Harpswell Sound.
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| Broad View |
Bailey Island
| 4 | 6 |
$1650
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 Beautiful ranch sits up high on Blueberry Lane on Orr's Island with views to the open ocean.
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| Bryant's Cottage |
Orr's Island
| 2 | 6 |
$1500
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 Perfect for a small family or couple, enjoy a large yard, water access, and Beautiful sunset views.
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| Camp Bullwinkle |
Harpswell
| 3 | 6 |
$1750
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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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 Private dock, a pebbly beach, surrounded by water on all 3 sides of the Cottage.
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| Cordovano |
Great Island
| 3 | 6 |
$2000
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 Charming cottage on tidal waterfront at Long Cove. Uneven walkway from driveway down to cottage.
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| Cove Cottage |
Orr's Island
| 2 | 3 |
$800
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 Cute and Comfortable cottage with nice fenced in yard on waterfront with steps to shore.
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| D'Amelios Cottage |
Bailey Island
| 3 | 6 |
$1400
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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 |
$2200
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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 |
$1375
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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 |
$2950
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details
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 Spectacular sunset views from the wrap-around deck of this comfortable ranch.
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| Gagnier's Cottage |
Bailey Island
| 2 | 6 |
$1100
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details
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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 |
$1975
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details
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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 Deepwater frontage on Harpswell sound. Spectacular westerly views. Gas fireplace!
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| Goldsmith House |
Bailey Island
| 3 | 6 |
$1900
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 Charming cottage has a large deck that overlooks Mackerel Cove!
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| Grey Cottage |
Bailey Island
| 2 | 4 |
$900
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 Enjoy the crashing surf and overview of Little Harbor at this charming cottage. The occupancy is limited to 6 max!
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| Grey Rocks |
Bailey Island
| 5 | 6 |
$1500
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 House sits right on the rocks at Water's Edge with it own dock and mooring.
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| Gull Perch |
Great Island
| 1 plus loft | 6 |
$2000
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details
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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 Cottage, 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 deck or down on the expansive deck at the dock. Enjoy as the sun rises from the East with spectacular views of the bay.
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| High View |
Great Island
| 2 | 6 |
$2200
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details
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 Classic Maine cottage looks out at Mackerel Cove with a wooded path down to the water.
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| Horner Cottage |
Bailey Island
| 2 | 5 |
$550
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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 either of the two open decks.
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| Inner Ledge |
Bailey Island
| 4 | 7 |
$3600
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details
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 Turn of century cottage with crashing surf and open ocean views!
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| Isle of View |
Bailey Island
| 4 | 8 |
$1850
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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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 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 |
$1475
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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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 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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details
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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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details
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 The Loft area is not suitable for small children!
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| Nautical Nest |
Bailey Island
| 1 | 2 |
$1000
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details
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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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details
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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 |
$800
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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 |
$3200
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details
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 Enjoy spectacular sunset views, a large deck, a sauna and jacuzzi tub.
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| Pennhils |
Bailey Island
| 3 | 6 |
$2000
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details
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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 |
$2800
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details
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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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details
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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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details
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 The Loft area is not suitable for small children!
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| Sea Scent |
Bailey Island
| 1 | 2 |
$1100
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details
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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 |
$1300
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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 | 5 |
$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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details
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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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details
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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 | 3 |
$600
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 This lovely cape with a nice yard, beautiful sunset views, and a rocky shore front.
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| Whitesails House |
Bailey Island
| 4 | 7 |
$2800
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