The rustic feel of the 1870 Monhegan House (1 Main St., 207/594-7983, www.monheganhouse.com , $135–165) is tempered by down-home accoutrements in the guest rooms, including gauzy white curtains and antique Victorian furniture. Guests congregate around a stone fireplace in the lobby or bump toothbrushes in the shared bathrooms on the second floor. Ask for a room with a lighthouse view.
Flags wave from the turret of the Island Inn (on the harbor, 207/596-0371, www.islandinnmonhegan.com , $195–255), a grand turn-of-the-century hotel overlooking a harbor full of lobster boats. Inside are painted reproductions of the inn by Andrew Wyeth, Rockwell Kent, and other Monhegan  artists. The inn’s 34 rooms are simple without being rustic, featuring painted floors and furniture and fluffy duvets to keep guests warm on chilly Maine  nights (like most of the accommodations on Monhegan, the inn is unheated).
For a bit more seclusion, Brackett’s Oar House (3 Fish Beach Ln., 207/594-9151, www.fishbeachmonhegan.com , $145) has an upper-floor apartment with a private balcony overlooking Fish Beach, the lighthouse, and the lobster boats bobbing in the harbor below. The apartment includes a full kitchen and outdoor grill. Its owner, Lisa Brackett, also rents other cottages around the island for longer stays.