Best Places to Stay on Casco Bay Islands

Take a vacation without leaving Portland by spending a night, a weekend, or longer on an island offshore. Even if your getaway is just a short ferry ride away, staying on an island feels like a true escape.

Hotels and Inns


Chebeague Island Inn

Painted yellow and set on a hill, Chebeague Island Inn is a beacon on Casco Bay’s largest island. With no two rooms alike, the inn is a distinctive vacation experience in itself. Beach cruiser bicycles, tennis courts, golf, and cornhole are some of the numerous amenities offered during a stay, but there’s also something to be said for kicking back in a rocking chair on the spacious porch or an Adirondack chair on the lawn. The menu in the dining room makes good use of local ingredients, including produce from Second Wind Farm on the island.


Inn on Peaks Island

Only a 15-minute ferry ride from Portland, the Inn on Peaks Island possesses true Maine island charm. Each room is bright, unique, and named after a surrounding island. The inn is walking distance from the ferry dock, and the onsite restaurant serves up fresh Maine seafood and local beer and soda from Shipyard Brewing Co. There’s a lot to do on Peaks: visit local art galleries, explore historic abandoned buildings, horseback riding, and ocean kayaking. See the island in an hour by walking the circumference, or bike it in about 20 minutes.


Inn at Diamond Cove

Built in the 1890s as the army barracks for Fort McKinley, the historic building that is now the Inn at Diamond Cove has 44 spacious rooms—many with balconies—a heated outdoor swimming pool and a restaurant that serves breakfast, lunch, and dinner. Among many other amenities offered at the inn are a fitness and activity center, tennis courts, hiking trails, and a private marina. Walk along the pebble beaches and experience a true island getaway.




Located eight miles off the coast of Portland, Jewell Island boasts hiking trails, camping spots, and abandoned buildings. Only accessible by private or chartered boat, this uninhabited island is rich with history and places to explore. Local volunteers and the Maine Island Trail Association (MITA) work in collaboration with the Maine Bureau of Parks and Lands to maintain Jewell Island, which is open to the public and free to visit.


Little Chebeague Island has a lot to offer in less than a mile and a half of space. There was a large military presence throughout Casco Bay during WWII, which left this island speckled with abandoned buildings. At low tide, Little Chebeague Island is connected to Great Chebeague Island by a walkable sandbar. With two different tenting sites, hiking trails, and gravel and sandy beaches, exploring Little Chebeague is easy. The island is free to visit, open to the public, and leashed pets are allowed.


Whaleboat Island is lesser known, and a little further away from Portland, however, it is Casco Bay’s largest wild island. With three established campsites available, this hidden gem has space for larger groups, offering five to six private tenting spaces at just one established area. There are no designated trails on the island, but dedicated hikers can follow the rocky shoreline at low tide. Visit in the springtime for some migratory bird watching, or catch the sunset over Casco Bay. With gravel beaches and scenic meadow views, Whaleboat Island invites endless exploration.


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