Chebeague Island Inn

The Chebeague Island Inn is a 1920s wraparound-porch summer hotel on a small island in Casco Bay, reached by ferry from Portland. Twenty-one rooms, a 9-hole golf course, a working dining room, and a deliberate pace that runs on island time rather than mainland time. It's the kind of inn that hasn't been redesigned to look modern, and the people who like it like it for that reason.

Chebeague is a year-round island community of around 350 residents. The inn is the largest property on the island and the closest thing to a public commons. Most guests arrive from Portland for a weekend and leave wanting to come back.

The setting

Chebeague is the second-largest of Casco Bay's Calendar Islands. The Chebeague Transportation Company ferry from Cousins Island (just north of Portland in Yarmouth) runs about fifteen minutes; the longer Casco Bay Lines ferry from downtown Portland takes about ninety minutes and stops at multiple islands en route. The inn is at the south end, near the ferry landing, with the 9-hole golf course on the bluff above the water.

Once on the island, you walk, ride a bicycle, or borrow one of the inn's vehicles. There are no rental cars and no Ubers.

The building

A large white-clapboard summer hotel on a low rise above Casco Bay, with a wraparound porch that runs the front length of the building. The interior has been kept in the period register — wide-plank floors, painted wainscoting, a sitting room with a fireplace, a bar that feels like it's always been there. Public spaces are restrained-Americana: clapboard porch, simple lighting, comfortable rather than designed.

The renovation work over the years has been careful rather than dramatic. The 1920s feel is intact.

The rooms

Twenty-one rooms across the main building. Categories range from compact rooms at the rear (around $495 in season) up through harbor-view rooms with the wraparound-porch access and larger floor plans. Beds are queens and kings, bathrooms are updated, linens are heavy. Most rooms have small windows rather than picture windows — this is a 1920s building and the bones reflect it. Several have small private decks.

Ask for harbor-side at booking; the rear rooms face the woods.

Food & drink

The inn's dining room is one of the better options on the island and is open to non-guests. Menu is Maine seasonal — local seafood, vegetables from island and mainland farms, a wine list weighted toward old-world bottles. Breakfast and dinner; the bar runs through the evening. There are a couple of casual lunch options elsewhere on the island, but the inn's dining room is the main reservation.

On the property

The grounds and the island shape the experience.

• 9-hole golf course (the Great Chebeague Golf Club, the country's oldest island golf course in some accounts)
• Wraparound porch with rocking chairs
• Bicycle rentals through the inn
• On-site dining room and bar
• Open seasonally (typically May through October)

Who it's for

• Couples doing a long weekend who want a real island, not a resort
• Golfers — the 9-hole course is unusual and worth the round
• Travelers who'd rather walk a beach loop than a hotel hallway
• Solo travelers — the inn's bar makes solo dinners easy

Who it's not for

• Year-round travelers — the inn is seasonal
• Families with very small kids who'd struggle with the ferry-and-island logistics
• Anyone who wants a full spa, gym, and 24-hour service

Nearby

The island itself is the main destination. Walk or bike the loop to Hamilton Beach and Indian Point; the island's roads cover about ten miles total. The 9-hole golf course is on the property's edge. For seafood-shack lunch, the Niblic Cafe near the ferry is the standard. From Portland, Old Port restaurants and the Portland Head Light are obvious before-or-after-island stops. Other Casco Bay islands — Peaks, Long Island, Great Diamond — are reachable on the same ferry network.