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While you’re soaking up as many final beach days as you can, you should also be making plans for next summer. But which Hamptons hamlet is right for you? We asked our friends at Out East to help us decide by sharing the details on the areas with the most affordable rentals, most private pools, best for large groups and more. Better act fast, though—the best summer homes always get snapped up fast.

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where to stay in the hamptons sagaponack
Out East

Most Expensive: Sagaponack

Low on nightlife but high on gorgeous landscapes, tiny Sagaponack is the most expensive place in the Hamptons for full summer rentals (and also in general). The average price of a rental from Memorial Day through Labor Day is $125,000 in the secluded hamlet. Even if you don’t have that kind of pocket change, we highly recommend scrolling through to ogle the listings, like this stunner, which features three working fireplaces and a location minutes from the beach. 

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where to stay in the hamptons east hampton
Out East

Most Private Pools: East Hampton

If your ideal summer involves lots of lounging poolside, East Hampton—with nearly 4,000 rentals with private pools—is the town for you. (Southampton is a close second with 3,700.) We’re already dreaming of weekends at this chic five-bedroom home that boasts a heated pool, a hot tub and an outdoor shower.

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where to stay in the hamptons southold
Out East

Most Affordable: Southold

We know Southold isn’t technically in the Hamptons, but with median rental prices of $30,000 for a full-term summer rental, it’s worth considering the North Fork. You can snag this four-bedroom, two-bath home that has plenty of room for entertaining for $26,000. Really want to stay in the Hamptons proper? Look to North Sea, Flanders and Hampton Bays, where the average Memorial Day to Labor Day rental will cost you $43,000. 

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where to stay in the hamptons southhampton
Out East

Best for Big Groups: Southampton

While Southampton comes up second to East Hampton in terms of number of rentals with four bedrooms or more, it’s a close runner-up. Plus, Southampton’s nightlife, boutiques and easy beach access are made for a group getaway. We’re bookmarking this giant seven-bedroom retreat with a sauna, steam room and indoor pool. Split between your squad, it’s…still expensive. (Worth it, though?)

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where to stay in the hamptons sag harbor
Out East

Most Dog-Friendly Rentals: Sag Harbor

Not gonna lie—pet-welcoming rentals are hard to come by in the Hamptons. Out East doesn’t track it as an amenity, but Sag Harbor—which is already known for its family-friendliness—has a number of rentals that mention dogs, such as this four-bedroom modern home just a block from Sag Harbor Cove.

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