Bailey Island, Maine Real Estate: 207-833-5078 Rentals: 207-833-7795 Ext. 18


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Basin Cove Cottage

Location: 165 Basin Point Road, Harpswell
In-Season Rate: $1200 per week
Within walking distance to the Dolphin Restaurant and the new boat launch / marina, this house is on Basin Cove and the views are into the cove! Sit on the deck and enjoy your morning coffee and enjoy your dinner at the table with a quiet breeze blowing! The house hosts 3 bedrooms all on the first...

Coveside Cottage

Location: 21 Coveside Road, Harpswell
Availability: Seaonsal June ~ October
In-Season Rate: $1,500 per week
Off-Season Rate: $1,500 per week
This cozy cottage faces north with great beachfront access within 25' in front of it and is an awesome spot for watching the sunset, going for walks, kayaking and of course if your daring going swimming! There is a small deck on the beach side, and the cottage is open and airy. There are two...

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 4 bedrooms, (1 King & 3 Queen) 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 glass treasures, or walk...


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...

Heart Cottage

Location: 103 Taylor Road, Harpswell, ME 04079
Availability: May-July, September-October ( August not available 2023 )
In-Season Rate: $3000 per week
Heart Cottage offers everything you want and more for your next Maine Coast vacation. Heart is located on the shores of Cundy's Harbor, Maine's oldest lobstering village. This amazing retreat offers an abundance of privacy, perfect for families to gather and enjoy the Maine coast. There is a large...


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...

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...

Mackerel Cove Condo

Location: Condo #3 Abner Point Road, Bailey Island
Availability: June - October

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...

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...

The Harbor House-Unavailable

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...

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...

Woodbine Cottage

Location: 139 Indian Rest Road, Harpswell Maine 04079
Availability: May-October 2023
Tranquility awaits! This completely remodeled and updated 2 bedroom cottage in the charming Indian Rest neighborhood offers gorgeous views of Gurnet Strait and has everything you need to relax on your next vacation! The fully equipped kitchen is open to the living room and dining area, making it a...