The South Fork of Long Island is a narrow strip with the Atlantic on one side and Peconic Bay on the other, and in places it is less than two kilometres across. That is the whole geography of the Hamptons, and it produces the only distinction that matters here.
Ocean side means the Atlantic: dune, surf, a beach that runs unbroken for kilometres, and sunrise over the water.
Bay side means Peconic and Gardiners bays: flat water, no waves, harbours, boats, and sunset over the water instead.
They are a mile apart and priced as though they were in different countries.
The other thing to know before booking
The Hamptons has very few hotels. This is a place of private houses, and the accommodation economy runs on summer rentals rather than rooms. Once the rentals, the bed and breakfasts and the guesthouses come out, the list of actual four and five star hotels across the whole South Fork is short.
That was planned at eleven and it comes to ten. Padding it would mean counting inns with four bedrooms.
The second thing is the season. Memorial Day to Labor Day is the Hamptons; outside it, a good proportion of the restaurants and several of the hotels close. September is the local's favourite month: warm water, no traffic and half the rates.
The ten below are grouped by which water they face.
Montauk, at the end
The last town on the fork, 190 kilometres from Manhattan, with a lighthouse, a working fishing fleet and both coasts within a few hundred metres.
Gurney's Montauk Resort & Seawater Spa occupies a bluff above a private ocean beach with a seawater spa, several restaurants and the only genuine oceanfront resort on the South Fork. It is the most complete hotel in the Hamptons.
Gurney's Montauk Resort & Seawater Spa
Montauk oceanfront · 4★ · $$$$
The only true oceanfront resort on the South Fork
Check availabilityMarram sits on the ocean in a reworked motel with a beach bar, a fire pit on the sand and a young, surf-led tone. It is the most enjoyable place to stay in Montauk.
The Surf Lodge occupies a position on Fort Pond, on the bay side, with a deck over the water that is the most photographed drinking spot on the East End. It is loud in season and that is the point.
The Surf Lodge
Fort Pond, Montauk · 4★ · $$$
The most photographed deck on the East End
Check availabilityGurney's Star Island Resort & Marina sits on Star Island in Montauk harbour with a marina, two pools and the calmest water of the group. It is the family answer at this end.
Montauk Yacht Club occupies a marina position on the harbour with straightforward rooms and the best value in Montauk.
Sag Harbor, on the bay
A former whaling port on the north side, with the best village centre on the East End.
Baron's Cove occupies a waterfront position on the harbour with a pool, a good restaurant and rooms looking at the boats. It is the most pleasant place to stay on the bay side.
American Beech Hotel - Greenport sits on Main Street in an 1846 building with eight rooms, a serious wine cellar and a bar that is the village's living room. It is the most characterful stay on the fork.
American Beech Hotel - Greenport
Sag Harbor Main Street · 4★ · $$$
An 1846 building with a serious wine cellar
Check availabilityBridgehampton, East Hampton and Southampton
The villages between, inland by a few minutes from both coasts.
Topping Rose House occupies an 1842 farmhouse in Bridgehampton with a pool, a farm supplying the kitchen and the best restaurant in the Hamptons. It is a short drive to the ocean beaches.
Topping Rose House
Bridgehampton · 5★ · $$$$
An 1842 farmhouse with the best restaurant here
Check availabilityThe Maidstone Hotel sits on Main Street in East Hampton in a 1750 building reworked with Swedish design and an art programme, minutes from the village and the beach.
The Maidstone Hotel
East Hampton village · 4★ · $$$
A 1750 building reworked with Swedish design
Check availabilityThe Montauk Beach House occupies a wellness estate in Water Mill with a structured programme, a spa and no children. It is inland and the setting is the product.
The Montauk Beach House
Water Mill · 5★ · $$$$
Adults-only wellness estate inland from both coasts
Check availabilityWhat we have left off
The summer rentals are excluded and they are the Hamptons. Between May and September the great majority of visitors are in a rented house rather than a hotel, and the rental market is larger than the hotel market by an enormous margin. They are houses, not hotels.
What to do
Swim on the ocean side and sail on the bay side. Coopers Beach in Southampton and Main Beach in East Hampton require permits or a walk in; ask your hotel how they handle parking, because in July it is the single most frustrating thing here.
Cycle. The back roads between the villages are flat, quiet outside peak hours and lined with potato fields and hedges.
Do the Parrish Art Museum in Water Mill, which is a Herzog and de Meuron building, and the Pollock-Krasner House in Springs, which is Jackson Pollock's studio with the paint still on the floor.
Montauk Point lighthouse, the bluffs at Camp Hero and the seals in winter are the reason to go all the way east.
Eat lobster rolls, drink at the North Fork vineyards across the bay by ferry, and book everything in season.
Practical notes
The drive from Manhattan is two and a half hours without traffic and four or more on a Friday in July. The Long Island Rail Road and the Jitney bus both run, and the seasonal Blade helicopter service does it in forty minutes.
Memorial Day to Labor Day is the season. September is warmer than June, quieter and cheaper. Winter is very quiet and much is closed.
Beach parking is permit-controlled in most villages and enforced.
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Questions people actually ask
Ocean side or bay side?
Ocean for surf, dunes and sunrise. Bay for flat water, harbours and sunset. A mile apart and a large price difference.
Why are there so few hotels?
The South Fork's accommodation economy is built on summer house rentals. Hotel rooms are a small fraction of the beds available.
When should you go?
September. Warm water, no traffic and much lower rates than July or August.
How many nights?
Three. Four if you are adding the North Fork vineyards.
If you only book one
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