Waterfront

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Cribstone Cottage

Location: Harpswell Islands Road, Bailey Island
Availability: Year Round Availability
In-Season Rate: ( July - August )
Off-Season Rate: (last week June/ first week September) week off season after first week of September

This one of a kind location is sure to be your favorite vacation destination. The Cribstone Cottage offers 3 bedrooms, (1 King & 2 Queen and 1 pull out queen sofa) 3 full baths, beach, deck, dock, and one of the most gorgeous views that Bailey Island has to offer. Walk the beach and search for sea...

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Dockside

Location: 59 Abner Point Rd #2, Bailey Island ME
Availability: May-October
In-Season Rate: 1475.00 weekly
Off-Season Rate: 1475.00 weekly

This beautiful condo is located on Bailey Island in Mackerel Cove.
Wake up each morning to the beautiful view of lobster boats heading out to haul or enjoy sitting on the deck with a drink overlooking the cove. This newly remodeled condo offers a Queen bed and full bathroom on the second...

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Heroux

Location: 14 Linwood Road, Bailey Island
Availability: Seasonal June ~ October
In-Season Rate: 2250/weekly
Off-Season Rate: 1350/weekly

A secluded setting, magnificent sunsets and beach are a few wonderful features at this cottage. The lawn is large and slopes to (Bailey Island) Lowell's Cove with a path to the beach. There is a great deck on the water side to enjoy the sunsets from. Outside there is a shower with hot and cold...

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Joan's Ocean View on the Point

Location: 17 Lubee Dr. Bailey Island, ME 04003
Availability: May-October
In-Season Rate: $2300 per week (July & August)
Off-Season Rate: $2000 per week

Joan's view is a lovely 1900's cottage perfectly perched directly on the waters edge. Private oceanfront, with panoramic views of Harpswell Sound. Enjoy the amazing sunsets on the waterfront deck. The home has a first floor bedroom with queen size bed and direct access to the deck, and gorgeous...

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Manderley Cottage

Location: Bailey Island
In-Season Rate: $2900 per week (May 4-October 5th, 2019)

Manderley Cottage is a year-round ocean front home on Bailey Island, with phenomenal ocean views over Harpswell Sound and the islands of Casco Bay. Enjoy the vista of beautiful sea views, busy lobster boats and peaceful kayakers from the spacious three sided deck, or from floor to ceiling picture...

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Seaside

Location: Wallace Shore Road Ext, Harpswell, ME
Availability: October-November and February-March
In-Season Rate: $4000 per week
Off-Season Rate: N/A

Discover your dream escape in this stunning single-family waterfront home nestled on the serene shores of Cundys Harbor. This fully furnished gem boasts three spacious bedrooms and two and a half baths, making it the perfect haven for families or those seeking a peaceful getaway. Wake up to...

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Shore Thing

Location: 57 West Shore Road, Bailey Island
Availability: available June 3 to June 24 and August 26 until October 7
In-Season Rate: $1600 per week

"Shore Thing" is a true gem. A small and cozy cottage situated on a sloping lawn with a full view of Harpswell Sound. Watch the lobster boats, the Schooner "Alert", and the ferry from Portland daily; as well as the beautiful westerly sunsets from your very private, spacious deck. The cottage is a...

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The Conifer Cottage

Location: 1 Conifer Lane, Orrs Island, ME 04066
Availability: May - October
In-Season Rate: $1800 per week ( July/August )
Off-Season Rate: $1600 per week ( May, June, September, October )

Escape to your own private summer oasis on Orr Island! This charming rental property has everything you need for the perfect summer getaway. Enjoy cooking up a feast on the propane grill, relaxing on the outdoor furniture while taking in the breathtaking easterly views of the open ocean. Inside...

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The Harbor House

Location: 34 Harpswell Harbor Drive, Harpswell, ME 04079
Availability: June 1 - November 1, 2023
In-Season Rate: $3500 per week

This beautiful home is nestled perfectly on Harpswell Harbor Cove with all the amenities needed for a relaxing vacation. This custom built home is elegantly styled, and the spaces are open, bright and beautiful. Sit down by the water in the Adirondack chairs or drink your morning coffee in the...

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The Seacatch

Location: 13 Lubee Drive, Bailey Island, ME 04003
In-Season Rate: $4000 ( in and off season ) per week / one week minimum

This BRAND NEW BUILD on Bailey Island just steps from Mackerel Cove, Mackerel Cove Beach and local lobster wharfs. Watch the sunset, hang out on the beach, enjoy central air, cable TV and wifi! This is a beauty, we are so excited to offer this to you, and to add the SEA CATCH to the list of our...

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