An honest guide to the local Hamptons so you can decide where to spend a lavish summer (or not)

Part of New York State is especially alluring for those looking for the perfect summer getaway. It’s not the upstate with its lush forests and mountain views, and it’s not the city with its infectious energy. They’re the Hamptons, and they’re also one of the only things Long Island’s little fish-shaped island is known for.

When it comes to planning a vacation to the Hamptons, it can be an overwhelming task with a total of 11 cities to choose from, each significantly different from one another. One of the locals on the other who might be trying to be temporary, here’s how to navigate each big city… and which to ignore.

Related: These Are The Rookie Mistakes To Avoid If The Hamptons Are Your Summer Destination

The affordable ones … Ish

Contrary to popular belief, not all towns in the Hamptons have gone out of their way for budget vacations. While they’re always mistaken about the high end of the “friendly” ones, these are the cities where you can probably get away with paying $ 150 per night rather than $ 300.

Westhampton

The “Hamptons” technically – geographically – begin with Westhampton. On the map, this precedes the split that separates the north and south forks. Despite being the furthest from the East End, it’s not actually the cheapest town in the Hamptons – but it’s a great place for young people looking for a taste of the real life of the Hamptons.

  • Average hotel: $ 190 to $ 220
  • Average Airbnb: $ 250 to $ 800

Quogue

Quogue follows Westhampton and bridges the gap between that and Hampton Bays. It is a nature lover’s paradise, with plenty of marshy and bay-side parks to navigate while visitors enjoy its semi-remote landscape of Shinnecock Bay. If you fancy getting up close and personal with the famous Pine Barrens, look no further. Watch for ticks.

  • Average hotel: $ 125 to $ 300
  • Average Airbnb: $ 140 to $ 300

Hampton berries

There are some locals who will say that Hampton Bays doesn’t really count as a Hamptons town, but that’s not true – it’s just the Hamptons’ only affordable town. That being said, it’s the best bet for those on a budget, and they’ll be happy to find that even the food costs are much lower here than a restaurant in, say, East Hampton. You could sacrifice the ocean beaches for those along Shinnecock Bay, but it’s worth avoiding wasting $ 350 for dinner, right?

  • Average hotel: $ 125 to $ 220
  • Average Airbnb: $ 65 to $ 325

Southampton: THE city of the Hamptons

This is the one most people have been waiting for, with Cooper’s Beach, the place to have your drink and soak up the rays of the sun while taking in a pristine view of the ocean … and it all comes at a price. That being said, Airbnb is without a doubt the best choice for those looking to shop in the village and eat lobster dishes while watching the sunrise. Plus, a comfortable cabin will feel so much better than a hotel after dealing with the three hours of traffic it took to get past Hampton Bays.

  • Average hotel: $ 320- $ 700
  • Average Airbnb: $ 200 to $ 900

Those who got stuck in the middle

Bridgehampton

More traffic will bring visitors to Bridgehampton, the quiet Hamptons town that sits inland but offers no respite from accommodation prices because of it. On the contrary, prices are going up, as it sits just before the more expensive part of the East End of Long Island. However, it is home to many artists, which makes it sort of a hub for anything creative. It also drives up the price. The small shops and boutiques, as well as the expansive art galleries, are worth it.

  • Average hotel: $ 300 to $ 775
  • Average Airbnb: On the entire grid depending on accommodation, $ 150- $ 1200

Sagaponack

Deep in Bridgehampton is the hamlet of Sagaponack. It is known for its farms, its status and the enormous wealth that comes from it. When it comes to vacations, it is best to book something nearby. Airbnb is the only logical choice, but be prepared to pay through the nose.

  • Average Airbnb: From $ 350 to $ 700

Wainscott

See above. So similar to Sagaponack that no explanation is needed, but the historic Tudor style homes are absolutely breathtaking. It’s just a shame that the cost of renting one is astronomical.

Sag Harbor: The Strange Out

Sag Harbor is beautiful and picturesque, and exactly what one would expect of a historic port city. It’s reminiscent of Cape Cod, with divine seafood restaurants and assorted views. However, the cost of the stay often makes it inaccessible – and unfortunately there aren’t many surrounding towns to book cheaper. For anyone who can fit this within their budget, it is well worth it for this city dripping with history and seaside charm.

  • Average hotel: $ 600 to $ 1,800
  • Average Airbnb: $ 280 to $ 500

Quietly overvaluing the rest

East hampton

If depositing $ 400 (minimum) at a hotel is within budget, there is no better place to do so than East Hampton. This quiet Hamptons town oozes luxury but errs on the quiet, sleepy side, with plenty to see and do. Its beaches are classic Long Island with dunes dominating either side of its oceanfront roads, it’s a foodie’s paradise with gourmet markets and boutiques awaiting impatient shoppers, and, in short, c ‘is wonderful. In addition, you may be able to see Ina Garten.

  • Average hotel: $ 400 to $ 500
  • Average Airbnb: $ 230 to $ 775

Amagansett

Amagansett is a very quiet town and its people like it. It’s gorgeous and semi-secluded, making it the perfect beachside vacation. However, it’s also quite small, and at the time of writing there are only a handful of Airbnbs available.

  • Average Airbnb: $ 275 to $ 1,200

Montauk: the end

Montauk lighthouse with the beach in the foreground

Jialin Hu on Unsplash

Literally, Montauk is the end of Long Island except for having a seaworthy ship in which to navigate its cliffs. At first glance, it might seem like there isn’t much here, but there isn’t. Montauk’s historic Lighthouse, Gossman’s Dock featuring classic seafood and shopping, plus a handful of bars and clubs line the Montauk Highway. In terms of price, it can be affordable if you book a hotel inland or find a small chalet to rent. It’s even more affordable out of season.

  • Average hotel: $ 400 to $ 700
  • Average Airbnb: $ 140 to $ 450

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