$100–150

The one, the only place to lay your head on Cuttyhunk is the Cuttyhunk Fishing Club (One, Road to the Landing, Cuttyhunk Island, 508/992-5585, www.cuttyhunkfishingclub.com, $164–185). Perched above the roaring ocean surf, the breezy building is much like the island itself: quiet, humble, and a little rough at the edges. Still, there’s a musty library filled with hurricane lamps and board games, and the hotel serves an extremely popular brunch on weekends.

Touristy Plymouth, meanwhile, has the lion’s share of the South Shore’s hotels and inns. Named after the long-necked flocks at the nearby beaches, the White Swan B&B (146 Manomet Point Rd., Plymouth, 508/224-3759, www.whiteswan.com, $120–175) is a simply decorated 1800s home with a surprising number of amenities, including wireless Internet, a whirlpool tub, hair dryers, and in-room fridges.

Overlooking the spot where the Mayflower hit dry land, The Governor Bradford Inn (98 Water St., Plymouth, 508/746-6200, www.governorbradford.com, $79–129) is actually more of a hotel than inn—the rooms have all the personal charm of a Ramada—but for pure proximity to Plymouth Rock, it can’t be beat.

Small, friendly, and a stone’s throw from working cranberry bogs, Cranberry Cottage Bed & Breakfast (10 Woodbine Dr., Plymouth, 508/747-1726) is home to four guest rooms (some with fireplaces), a pool, and outdoor games like horseshoes, badminton, and table tennis.

$150–250

More of a residential than resort community, Duxbury really has need for only one inn, but it’s a lovely one. Surrounded by impeccably kept gardens, the
1803 Winsor House Inn (390 Washington St., Duxbury, 781/934-0991, www.winsorhouseinn.com, $110–210) houses an English-style pub and rooms with antiques, canopy beds, and an impressive homemade breakfast.

© Michael Blanding and Alexandra Hall from Moon New England, 2nd Edition