Kristin Tieg Photography / Courtesy of Chebeague Island

Chebeague Island Inn, Chebeague Island, ME

3 of 22

This restored 1920s Greek Revival inn overlooking the ocean lies on one of Maine’s most beautiful islands in Casco Bay, a 25-minute water taxi ride from Portland and its bevy of hip restaurants. After a day of leaf peeping and lobster boat sightings, kick back on the porch or in front of the stone fireplace in the Great Room. Doubles from $305.

Room to Book: An ocean-view room with a private bath. It comes tailored in crisp ginghams and plaids with a queen-size bed and works by local Maine artists.

Get Outdoors: Walk to the rocks at Deer Point for fantastic views of the bay and island.

America's Best Hotels for Fall Colors

Chebeague Island Inn, Chebeague Island, ME

This restored 1920s Greek Revival inn overlooking the ocean lies on one of Maine’s most beautiful islands in Casco Bay, a 25-minute water taxi ride from Portland and its bevy of hip restaurants. After a day of leaf peeping and lobster boat sightings, kick back on the porch or in front of the stone fireplace in the Great Room. Doubles from $305.

Room to Book: An ocean-view room with a private bath. It comes tailored in crisp ginghams and plaids with a queen-size bed and works by local Maine artists.

Get Outdoors: Walk to the rocks at Deer Point for fantastic views of the bay and island.

Kristin Tieg Photography / Courtesy of Chebeague Island

America's Best Hotels for Fall Colors

Explore More