3 Best Hotels in Side Trips From Portland, Maine

Background Illustration for Hotels

We've compiled the best of the best in Side Trips From Portland - browse our top choices for the top things to see or do during your stay.

Chebeague Island Inn

$$$ | 61 South Rd., Casco Bay Islands, ME, 04017, USA

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 executive chef Marsh Elliot, whose way with seafood (don't miss the pollock schnitzel with artichoke relish) is remarkable. 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 turndown service.

Pros

  • Top-notch food
  • Stunning ocean views and sunsets
  • Individually decorated rooms

Cons

  • No televisions
  • No air-conditioning
  • Not much else going on beyond the inn
61 South Rd., Casco Bay Islands, ME, 04017, USA
207-846–5155
Hotel Details
Closed Oct.--May
21 rooms
No Meals

Quick Facts

Something incorrect in this review?

Inn at Diamond Cove

$$$ | 22 McKinley Court, Casco Bay Islands, ME, 04109, USA

Transformed from Fort McKinley, an 1800s United States Army coastal defense fort, into a modern and swanky inn, this sprawling property welcomes guests with 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.

Pros

  • An outdoor pool
  • Luxury rooms and suites, many with fireplaces
  • Lots of amenities, from tennis and biking to a game room

Cons

  • Your arrival and departure is determined by the ferry schedule
  • There's not much to do outside the resort
  • On island transportation is via bike or feet
22 McKinley Court, Casco Bay Islands, ME, 04109, USA
207-805–9836
Hotel Details
Closed Oct.–May
44 rooms
No Meals

Quick Facts

Something incorrect in this review?

Inn on Peaks Island

$$ | 33 Island Ave., Casco Bay Islands, ME, 04108, USA

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 very good on-site restaurant serving breakfast, lunch, and dinner.

Pros

  • Easy walk from the ferry terminal
  • Jacuzzi bathtubs in many rooms
  • Most rooms have water views

Cons

  • Limited services offered in the off-season
  • Arrival and departure dictated by the ferry schedule
  • The restaurant has seasonal hours
33 Island Ave., Casco Bay Islands, ME, 04108, USA
207-766–5100
Hotel Details
Closed Mon.–Wed.
8 suites
No Meals

Quick Facts

  • $$

Something incorrect in this review?

Recommended Fodor's Video

Not finding what you're looking for?

We've got a few suggestions for nearby spots.
$$ Bar Harbor Fodor's Choice

Highbrook Motel0 miles away

94 Eden St., Bar Harbor, Maine, 04609, USA
We recommend 4 Hotels in Bar Harbor
$$$ Millinocket Fodor's Choice

Libby Camps0 miles away

Millinocket, Maine, USA
We recommend 2 Hotels in Millinocket
$$$ Millinocket Fodor's Choice

New England Outdoor Center0 miles away

30 Twin Pines Rd., Millinocket, Maine, USA
We recommend 2 Hotels in Millinocket
$$ Rockland Fodor's Choice

250 Main Hotel0 miles away

250 Main St., Rockland, Maine, 04841, USA
We recommend 3 Hotels in Rockland
$$$ Greenville Fodor's Choice

Appalachian Mountain Club Maine Wilderness Lodges0 miles away

North Woods outside Greenville, Greenville, Maine, USA
We recommend 2 Hotels in Greenville