3 Best Hotels in Side Trips From Portland, Maine

The focal point of Chebeague Island's activity, the Inn is a destination in its own right for golfers, tennis players, and food lovers looking to try the creations of 2018 Food Network Chopped award-winner, chef Matt Ginn. Visitors are rewarded with all of the above, and those staying the night can expect individually decorated rooms (with either ocean views or garden views), filled with local art, Italian hem-stitched linens, and nightly turn-down service. 

Transformed from Fort McKinley, an 1800s United States Army coastal defense fort, into a modern and swanky inn, this sprawling property welcomes guests for overnight stays or for dinners and lunches. It offers myriad things to do: play some tennis or indoor basketball; lounge at the pool; meditate in the yoga studio; or grab one of the complimentary bikes and explore the nearby trails. Best of all, though, may be the three dining options: the sleek lobby bar; the poolside cabana and firepit serving pizza and sandwiches; and the lovely waterfront Diamond's Edge Restaurant + Marina, which is a magnet for those coming by boat just to enjoy its refined menu of New England dishes. 

Boasting spacious rooms with water views and Jacuzzi tubs in many of them, this year-round favorite blends a relaxed, island style with a dash of luxury; rooms are decked out in simple but pretty linens and soft patterns. Central to everything near the ferry, it offers free parking (Peaks Island is the only one accessible by ferry which allows visitors to bring a car) and has a good on-site restaurant serving breakfast, lunch, and dinner. Specialties such as Bangs Island mussels with kielbasa and roasted red peppers lead into substantial entrées like fish tacos and fried haddock sandwiches. Kids swoon for the epic brownie sundae at dessert time.