Hidden Gems in the Hamptons: How to Find Perfect Summer Rental

It’s not too late to find the perfect summer rental home in the Hamptons for 2023. But it will be soon! Here’s our guide to the Hamptons, and our insider tips on how to find the perfect summer rental that fits your tastes and budget this year.

Hidden Gems in the Hamptons

Looking for the perfect Summer rental home in the Hamptons for summer 2023? Have a look at our 9-step guide to finding the perfect luxury rental. And assess which of the 7 social circles in the Hamptons suits you best. Then check out some of the specific fun facts and good things to know that we have uncovered, as well as some specific properties that are currently for rent that caught our eye (perhaps this one in Water Mill that The Post is calling the “priciest-ever Hamptons summer rental ever” at $2.5 million for three months which comes out to $833,333 per month or about $25,510 per day.)

We’ve also noted our favorite hotels and restaurants, should you decide to visit before you make your final rental decision. Summer’s almost here. Let’s make plans! Most of our staff are New Yorkers, so we know from the Hamptons – here’s how to find the best luxury summer rental home for you in 2023.

the hamptons 101: the basics to know to find the best luxury summer rental home

The iconic Hamptons are comprised of a group of 10 towns on the South Fork that are collectively the summer playground of choice for many players in the global elite. Think bold-faced names in fashion, media, publishing, entertainment and finance.

This scene is not for everyone — it’s basically Manhattan on the Beach, and you need to dress appropriately — but if you’re up for it, there’s no better place to experience summer luxury (at least in the US). With numerous art galleries, museums, charming shops and gorgeous beaches – plus lots of celebrity-spotting and glamorous parties – there’s very little not to like for luxury lovers.

It’s easy to get distracted by the Hamptons infamous opulence. But there is more to a summer in the Hamptons than all the glitz. Captivating, world-class beaches of white sand and dramatic dunes await. It’s the epitome of Atlantic coastal beauty, with spectacular light that has inspired painters like Jackson Pollack and Winslow Homer. If you’re lucky enough to rent a home or be invited to one, it will be an experience you won’t soon forget.

Here’s how to find the best luxury summer rental home in the Hamptons in 2022, including what to know and specific properties on the market.

specific villages and homes to consider for luxury summer rental home in the hamptons 2023

1. East Hampton.

We love East Hampton because it has stellar beaches (we’re looking at you, Georgica), tons of upscale shopping, a great bookstore, and top-notch restaurants. The ultra-rich love East Hampton because they can get away from the hustle and bustle with stunning private homes along the ocean or behind thick green hedgerows.

Available Rentals. 

If you’re looking for the cream of the crop (or just want to ogle the inside of a spectacular home) check out this quintessential 12-bedroom and 9-bathroom Main Beach house. From the sweeping porch to the short walk to the beach and the game room and pool tables for long nights and rainy days, you can’t go wrong with this property. Or opt for this serene rental next to all your favorite high-end boutiques, restaurants, and grocery stores! The 3-bedroom that sleeps 6 is close to the beach and has a gorgeous pool and patio perfect for a classic summer barbeque. Drive, bike or walk and you’re at Main, Wiborg, Egypt or Georgica beach strolling or relaxing! 

Luxury Hotels. 

Baker House 1650; The Maidstone; The 1770 House; East Hampton House Resort; The Hedges Inn

Favorite Restaurants. 

Fresno; Nick & Toni’s; East Hampton Grill; Highway Restaurant

2. Southampton

The village of Southampton puts all other South Fork villages to shame when it comes to shopping, celebrities and real estate; you’ll see more luxury convertibles passing by on the street in 10 minutes than you’ve seen all year. Multi-million dollar mansions by the sea abound, as do popular clubs and restaurants.

Available Rentals:

This 4-bedroom 4-bathroom Southampton property will help you create such great memories with its spacious eat-in-kitchen with island, living room, dining room,  and laundry. Plus, a pool and large yard for the kiddos to run around and play. But what about this 2017 architectural gem in Water Mill that will make you feel like you are in a Nancy Meyers movie (look at those hydrangeas.)  The 4 bed and 4.5 bathroom home is 6 minutes from Flying Point Beach, 5 minutes to Southampton Village, 10 minutes to Bridgehampton and Sag Harbor.

Luxury Hotels.

Latch Pop Up Inn; Topping Rose House; Capri

Favorite Restaurants.

Sant Amboeus; Tutto il Giorno; Jue Lan Club; Southampton Social Club

3. Sag Harbor 

Sag is one of the prettiest towns on the South Fork. Charming storefronts line Main Street, alongside outstanding restaurants.  Here you’ll find artists, writers, the homes of many of the long-time African-American summer residents of the Hamptons, incredible sunsets, and the popular Long Beach.

Available Rentals. 

You will fall in love with this charming Sag Harbor property. With immediate beach access and tennis court, this 5-bedroom and 4-bathroom house including a private master suite with a sitting area, a luxurious master bath with spa/soaking tub and a chef’s kitchen. Plus, you are only 5 minutes from Sag Harbor Village. Escape the city and cozy up by the outdoor fire part in this elegant country house. With five bedrooms this would be great for a large group of friends or a family. 

Also check out this modern, waterfront property that offers water views from nearly every room, complete with a private dock for sunset cruises on your boat. 

Luxury Hotels. 

The American Hotel; Baron’s Cove

Favorite Restaurants. 

Le Bilboquet; Lulu Kitchen & Bar; The Beacon; Page at 63 Main; Wolffer Kitchen; Grindstone Donuts, Dockside Bar & Grill

4. Shelter Island.

If you don’t want to be in the Hamptons, but still want to be away for the summer Shelter Island could be for you. Shelter Island is known for its natural beauty – and for being markedly more low key than its flashier neighbors in the Hamptons. Read more about its history here. 

Just north of most of the action, the aptly-named Shelter Island remains one of the most serene locations in all of the Hamptons. You’ll find lovely beaches, sunsets, restaurants, and homes – minus the hustle, bustle, and drama. The downside? You have to take a ferry to get there.

Available Rentals. 

This is the true definition of a beach house. You will feel like you are outside even when you are inside in this 4 bedroom house that features views of Orient Point, Gardiners Bay, and Mashomack Preserv. Have all the summer fun on Primrose Place in this 4 bedrooms, 3 bath home with a beautifully placed pool as well as a firepit, gazebo, and lounges. Fast access to shops, the beach and ferries. Dogges are welcome!

This amazing  historic compound on pastoral grounds has been renovated with all the modern conveniences and tasteful decor. Can someone rent this glamorous 6-bedroom waterfront villa and invite us over for a weekend? Inspired by a nautilus shell, this Frank Lloyd Wright and John Lautner styled 2-bedroom house is incredibly stylish and tranquil, perfect to summer in with another couple.

Luxury Hotels. 

Sunset Beach; The Chequit,  Ram’s Head Inn, The Pridwin. This is the first summer The Pridwin will be fully open after two years of extensive renovations by Cape Resorts. With a  private swimming pool and beach overlooking the 120-foot east and west docks,, it is impossible to have a bad time here. 

Favorite Restaurants. 

Sunset Beach Restaurant; Vine Street Cafe; Whale’s Tale; 18 Bay

5. Montauk.

Furthest east is Montauk, where during the day surfers flock to Ditch Plains Beach for the best waves on Long Island. After dark, the pubs take over with a nightlife scene that draws both hipster and local crowds.  The sunsets and beaches here are unforgettable.

Available Rentals.

There is a reason this house is called Paradise Found. The 4-bedroom bayfront property with direct water frontage on Fort Pond Bay has a  2 bedroom guest cottage, private 60 foot heated saltwater Gunite pool, private stairs to sandy bay beach, outdoor movie screen for summer movie nights on the bluff, outdoor fire pit, outdoor play structure, and a zip line. 

Escape the busyness of the city with this gorgeous house that is an oasis for golf lovers.  The 3 bed 3 bath home is a quick walk from Montauk Downs featuring golf, tennis, pool and dining. Watch golf all day from the 2 large upper decks.

This colorful 1-bedroom retreat with a private staircase to the beach has your names on it. For extended families, this sprawling 5-bedroom home is full of character and designed for entertaining.

Luxury Hotels.  

Montauk Beach House; Gurney’s; Hero Beach Club; The Crow’s Nest; McKinley Bungalow

Favorite Restaurants. 

Ruschmeyer’s; Dave’s Gone Fishing; Arbor; Flagship; Grey Lady; Navy Beach; Inlet Seafood Restaurant; Scarpetta Beach

6. Bridgehampton

Bridgehampton is one of the more low-key spots in the Hamptons. Main Street is filled with unique boutiques, art galleries and lovely restaurants. The equestrian crowd will be out in force here for the annual Hampton Classic Horse Show in late August.

Available Rentals. 

If you are looking for a shorter-term rental with all the luxury amenities and for a large group (perhaps an epic birthday or a combination of families) then you must check out this sprawling 17,000  sq ft estate with 11 rooms that sits on 11.5+/- acres of breathtaking land just south of the highway in Bridgehampton with an olympic-sized pool. For a bit more quaint (though no less luxurious) consider this charming  4-bedroom property with a chef’s kitchen, heated gunite pool and plenty of indoor and outdoor entertaining space.  

Serenity abounds in this contemporary shingled villa with a pool and hot tub and it’s a 5-minute drive from Sagg Main Beach.

Luxury Hotels. 

Bridgehampton Inn; Topping Rose House; Room at the Beach

Favorite Restaurants.

Pierre’s; Almond; Elaia Estiatorio

How to find the best luxury summer rental home in the Hamptons 2023

We hope this helps you find your perfect rental home in the Hamptons this summer. Good luck!