Your Stay in Bailey Island Starts Here

When you are on a search for vacation rentals in Bailey Island Maine, know that the coastal Maine around Bailey Island has 216 miles of coastline and more than 200 small islands accessible only by boat. The area is notable for its beautiful, yet rugged, scenery. The peninsula offers some great views, with numerous coves to explore. Locals refer to one of the better-known coves as the Basin. It is located a little over a mile by boat or 22 miles by car northeast. Vessels intending to sail around the harbor may wish to arrange a mooring at the Holbrook General Store. Summer marks the height of the tourist season, and vacationers will find the harbor a fine place to kayak and to swim. It bears repeating that the village is not a party spot. Rather, it is perfect for the vacationer who wants to leave the city behind in favor of a lush, relaxed environment. Nonetheless, Bailey Island contains many fun things to do. The village includes the usual amenities one would expect in a small town. It is home to a small library, adjacent to a pleasant little park that offers a fine view of the harbor. Unsurprisingly, several fine lobster eateries are scattered throughout the area, including the Holbrook Store, which also includes a restaurant and accompanying wharf. Meanwhile, the Harbor Works Gallery showcases maritime art, much of it locally made. Finally, those looking to explore beyond the village will find cliff trails and a state park just outside of Harpswell proper. There are three large islands connected to the mainland by bridges. The island has a serene way of life amid its abundance of natural beauty, is one of the few working harbors on the Maine coast, has beaches and fantastic walking trails, and offers authenticity and history. Bailey Island originally had the name Newaggin, which was given by the local Abenaki Native Americans, and it was populated by European settlers in the 17th century. You may want to visit Mackerel Cove, which is one of Maine's most photographed places, as well as Land's End's famous rocky beach. See the replica bronze statue of the 'Maine Lobsterman' from the 1939 World's Fair. Some of the other attractions that visitors love includes: The Bailey Island Cribstone Bridge was completed in 1928 and is the world's only Cribstone bridge. The unique design allows the substantial tides to flow freely through it, which greatly reduces the effect that the flow would have on boats going through its narrow opening in the channel. Giant's Stairs Trail, also called The Giant's Steps, is an unusual rock formation resembling a large flight of stairs and is similar to the Giant's Causeway in Ireland. After heading down a steep hill that has a gravel walk, you can sit on the rocks above the water, listen to the waves crashing against the rocks below, take outstanding pictures, and see the breathtaking rocky cliff and ocean views. Sea Escape Charters operate two, four, or six-hour tours, and a sunset cruise on Casco Bay's sparkling green waters as well as offering overnight camping trips. You are able to help get under sail by raising the sails or just choose to sit back and enjoy the sailing. The ship is comfortable and well maintained, and the family crew tells interesting stories and provides entertainment and homemade snacks. Bailey Island, Maine vacation rentals give visitors an opportunity to experience a unique location that is not only beautiful but also has a variety of unusual attractions

Stormhaven

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From $186/night
  • 8 Guests
  • 4 Beds
  • 2 Bath
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Drake

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From $100/night
  • 2 Guests
  • 1 Beds
  • 1 Bath
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Homeport Cottage

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From $129/night
  • 4 Guests
  • 1 Beds
  • 1 Bath
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Sea Chaser Cottage

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From $200/night
  • 4 Guests
  • 2 Beds
  • 1 Bath
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Sand-Dollar-Rental

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From $134/night
  • 2 Guests
  • 1 Beds
  • 1 Bath
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Lee-Rental

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From $193/night
  • 6 Guests
  • 3 Beds
  • 2 Bath
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Berkshire

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From $107/night
  • 5 Guests
  • 3 Beds
  • 1 Bath
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Coveside

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From $157/night
  • 6 Guests
  • 3 Beds
  • 1.5 Bath
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Addison-Red

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From $104/night
  • 5 Guests
  • 2 Beds
  • 1 Bath
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Anchorage-Rental

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From $114/night
  • 6 Guests
  • 3 Beds
  • 1 Bath
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Channeled Whelk

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From $225/night
  • 7 Guests
  • 4 Beds
  • 3 Bath
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Goldsmith-House

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From $257/night
  • 6 Guests
  • 3 Beds
  • 2 Bath
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Tree-Tops-House

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From $214/night
  • 11 Guests
  • 5 Beds
  • 2 Bath
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Harbor's Edge

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From $129/night
  • 4 Guests
  • 1 Beds
  • 1 Bath
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Satterthwaite

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From $114/night
  • 7 Guests
  • 4 Beds
  • 1.5 Bath
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Garrison Cove Cottage

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From $120/night
  • 2 Guests
  • 1 Beds
  • 1 Bath
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Thorburn Cottage

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From $157/night
  • 6 Guests
  • 3 Beds
  • 1.5 Bath
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Hay

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From $111/night
  • 6 Guests
  • 3 Beds
  • 1.5 Bath
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Whitesails-Cottage

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From $93/night
  • 3 Guests
  • 1 Beds
  • 1 Bath
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Safe Haven

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From $257/night
  • 6 Guests
  • 3 Beds
  • 2.5 Bath
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