
Pleasant Bay, Harwich
Wequassett Resort & Golf Club
Golf, several pools and a long-held kitchen reputation
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Cape Cod, Nantucket and Martha's Vineyard, USA
The island went broke when whaling ended, the population fell by two thirds, and nobody rebuilt anything for a century. That is why it looks like that.
The places to stay

Pleasant Bay, Harwich
Golf, several pools and a long-held kitchen reputation
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Brewster
A 1907 mansion estate with two courses and a private beach
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Nantucket town
A pool and family facilities, unusual on the island
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Edgartown, Martha's Vineyard
An 1890s porch with the lighthouse along the beach
Explore HotelBy Happi · Last updated September 2026
A little local perspective
$$$ to $$$$ — roughly $450-1,500 a night, roughly double in August
Nantucket looks uniform because it is required to. The entire town is a historic district and every exterior alteration — window proportions, trim colour, the pitch of a roof, the placement of a satellite dish — goes before a commission that has been enforcing the same standards since 1955. Cedar shingle, left to weather grey. White trim. Utilities out of sight.
The result is one of the most architecturally consistent towns in the United States, with more than eight hundred pre-1850 structures still standing, and the reason they survived is that the island went broke. Nantucket was the whaling capital of the world until the 1840s, when the Great Fire, the shift to petroleum and a sandbar that kept larger ships out ended it. The population fell by roughly two thirds and nobody rebuilt anything for a century.
Cape Cod is the mainland arm, reachable by road, with the outer beach protected as a National Seashore since 1961 — forty miles of dune and Atlantic surf that would otherwise have been developed.
Nantucket is thirty miles out, an hour by fast ferry from Hyannis or two and a half by the slow boat with a car. Cars require a reservation months ahead and most visitors do not bother.
Martha's Vineyard is closer in, forty-five minutes from Woods Hole, larger and more varied — six towns ranging from the gingerbread cottages of Oak Bluffs to the clay cliffs at Aquinnah.
In July and August the ferries are the constraint on everything. Book them before the hotel.
The ten below are grouped that way.
The mainland arm.
Chatham Bars Inn occupies a 1914 hunting lodge and its cottages on a private beach at Chatham, with a spa, several pools and a boat to the outer bar for seal watching. It is the best hotel on the Cape.
Wequassett Resort & Golf Club sits on Pleasant Bay at Harwich with a golf course, several pools and a kitchen that has held a reputation for decades.
Ocean Edge Resort & Golf Club occupies a 1907 mansion estate at Brewster with two golf courses, a private beach and full family facilities.
Thirty miles out.
The Wauwinet occupies a position at the far end of the island on Nantucket Sound, reached by a long sand road, with its own beach on two sides and a restaurant that people take the boat out for.
White Elephant sits on the harbour in town with cottages and a main house, a lawn to the water and the shops a few minutes away.
Greydon House occupies an 1850s house on Broad Street, reworked with a small room count and a bar that is the island's best.
The Nantucket Hotel & Resort sits a short walk from Main Street with a pool, a garden and family facilities that are unusual on the island.
Forty-five minutes from the mainland.
Harbor View Hotel occupies a set of 1890s buildings on the Edgartown harbour with a wraparound porch, a pool and the lighthouse along the beach.
The Charlotte Inn sits in Edgartown in a group of nineteenth-century houses around a garden, with an art collection and a deliberately hushed tone.
Winnetu Oceanside Resort occupies a position on South Beach at Katama with cottages, a pool and direct access to the Atlantic side.
The house rentals across all three are excluded, and in July and August they are how the overwhelming majority of visitors stay, frequently booked a year ahead by the same families. They are houses rather than hotels.
Book the ferry first, and the car reservation before that if you insist on bringing one. On Nantucket you do not need one.
Cycle. Nantucket has about fifty kilometres of flat paved bike paths linking the town to Madaket, Surfside and Sconset, and it is the sensible way around.
Walk the Cape Cod National Seashore beaches, and note that white sharks have returned to this coast following the grey seal recovery. Beaches post daily advisories and they are worth reading.
See the Whaling Museum on Nantucket, which is in a restored spermaceti candle factory and explains how the island got rich and then did not.
Eat oysters at Wellfleet, where the harbour has been producing them commercially since the seventeenth century.
Boston is about ninety minutes to Hyannis by road. Both islands have small airports with seasonal flights from Boston and New York.
Late June to early September is the season and it is intense. May, early June and September are the best weeks — warm water, open restaurants, no queues. Most of the islands close down substantially from November to April.
Rates in August are roughly double the shoulder season.
Prices shown are sample rates from upcoming dates — not quotes for specific dates. Open a hotel and choose your own dates and guests to see the exact price.
Every exterior detail is governed by a historic district commission, and the town's poverty after the whaling collapse meant nothing was rebuilt for a century.
Not on Nantucket. Vineyard yes if you want the whole island, and ferry car slots book months ahead.
Nantucket for architecture and cycling, the Vineyard for variety and six different towns, the Cape for the National Seashore.
Six. Three on an island and three on the Cape.
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