How to Weekend in the Hamptons: where to stay and what to do

A classic cedar shingled beach house in the Hamptons on Long Island

A classic cedar shingled beach house in the Hamptons


If you don’t have your mansion, summer share house or cottage, it can be difficult to access the Hamptons for just a weekend. Luckily there a few new artful country inns and boutique hotels so now we can all escape New York and enjoy a Hamptons weekend getaway. Here is the rundown on where to stay and what to do.

I checked out a couple recently with my oldest daughter, grown up and living in New York, to see if the weekend boutique hotel experience is all its cracked up to be. They may be a bit pricey but it’s nothing compared to summer house rentals.

Prices in the Hamptons can really take your breath away….Beyonce paid US$400,000 to rent a 14-bedroom mansion for one month; if you were so inclined, you could have bought the same five hectare estate with pool, tennis court, bowling alley, theater and eight-car garage for US$43.5 million. Yet, in spite of its excesses, much of The Hamptons’ appeal is priceless.

Vistas of translucent light over dune grasses to the sea attracted artists more than a century ago to this 50-kilometer stretch dotted with a handful of villages on the eastern end of Long Island. New York Society followed, building grand cedar-shingled mansions on the potato fields and riding horse buggies down its rose-rimmed country lanes to the beach.

In addition to Hollywood celebrities and New York’s elite, plenty of regular folk rent cottages for the summer season.  I did just that with my young family for many years, biking to

East Hampton style

East Hampton style

beaches that stretch for miles (with no hotels or condominiums thanks to those expansive estates), picking strawberries, buying produce at farm stands, toasting marshmallows over beach bonfires, and visiting yard sales.  Now there’s a fascinating Hamptons activity. You may not meet the celebrities but you can  find their discarded treasures. Once I scored a silver bowl from Martha Stewart’s daughter.  On the bottom, it had a sticker: “first prize, premier bitch class.” I kid you not.


C/0 The Maidstone boutique hotel

C/o The Maidstone exudes a relaxed Bohemian ambiance that is a perfect antidote to manic Manhattan. We love the quirkiness from the moment we step onto the porch of the historic two-story building. It is decked out with sheepskin-draped Swedish metal garden chairs and doggie water bowls. The cozy bar and dining area is a smorgasbord of bright florals and black and white photographs while each of the 19 rooms, including three cottages, is designed after a Scandinavian luminary. Think Karen Blixen and Hans Christian Anderson.

Sag Harbor

We head out to Sag Harbor, a former whaling town and delightful year-round community that still has a soul as well as a bookstore, hardware store and even a five and dime. It manages to balance the extremes of East Hampton, where Ralph Lauren, Gucci and Tiffany have elbowed out many authentic local spots. Stopping first at retro-heaven LT Burger, we feast on hamburgers and fries with classic shakes from the soda fountain, then explore the likes of Donna Karan’s Urban Zen and check out what’s playing at Bay Street Theater, run by Julie Andrews daughter.

Grabbing a table on The American Hotel exudes old world charm in the old whaling town of Sag Harborthe terrace of the 1842 American Hotel, on Main Street, we toast the summer breeze at this clubby spot, which is popular with the literary and chatty set. Back in the bijou Living Room at c/o The Maidstone we savor chef James Carpenter’s trailblazing slow food delights like salmon tarte flambée with crème fraiche, washed down with an organic wine from Long Island.


C/o The Maidstone lends guests classic tomato-red Kronen bicycles and next day we pedal along country lanes to Southampton, passing many a colossal mansion but also one-room schoolhouses, horse farms, a rickety bridge, and fields brimming with corn, zucchinis, strawberries and sunflowers. Southampton oozes Old Money with historical mansions tucked behind trimmed hedges. Its white weatherboard main street mixes old-style fixtures such as Hildreths (America’s oldest home goods store still delivering classic Hamptons beach style) with the uber-hip Tripoli Gallery.

East Hampton

Returning to c/o the Maidstone we collect a gourmet picnic basket along with deck chairs, umbrella and the essential beach parking sticker.  Heading to East Hampton’s uncrowded Egypt Lane Beach beside the manicured fairways of the genteel beach-side Maidstone Club, we then walk for miles along East Hampton Main Beachbusy Main Beach with its classic bathhouse, to Georgica Beach and its pretty pond dotted with wooden sailboats.


That evening, we head east to Montauk, formerly a daggy beach town but now tricked up with retro joints popular with New York’s 20-somethings. Ruschmeyer’s is the epicentre, a sort of family camp for East-End hipsters (now called Hampsters, get it?) and their groovy offspring.  The place is packed. Kids are painting in a tepee pitched in a magic garden draped with lanterns. We order Electric Eel vodka, pineapple and sage cocktails and check out ping pong and bocce on an outdoor sandpit. The verdict: Ruschmeyers is perfect for my daughter’s age, but for me, c/o The Maidstone has everything you need for an ideal Hamptons weekend.

Where to Stay:

C/o The Maidstone in East HamptonEclectic, quirky and colorful defines the personality of c/o The Maidstone  which blends bold Scandinavian design with a classic 1800s clapboard building across from the East Hampton town pond.

Ruschemeyers is a cleverly re-imagined 50s-style motel in Montauk that offers cabins with cedar-planked walls and suspended Macrame hanging chairs. Beware the bar scene can get pretty boisterous but the food is excellent.

The new Topping Rose House located in a beautifully restored Greek Revival-style mansion in Bridgehampton is the first full-service luxury boutique hotel to open in The Hamptons. New York chef Tom Colocchio, of Craft restaurants fame, is running the restaurant.

What to do:

If you are so inclined, shop till you drop. East Hampton has all the big name brands such as Tiffany, Gucci, and Ralph Lauren.

Explore The Longhouse Reserve’s 16 acres of sculpture-dotted gardens in East Hampton owned by textile designer Jack Lenor Larsen and the Madoo Conservancy in Sagaponack, with its Tudor, Early Greek and Oriental gardens designed by artist and writer Robert Dash.

Farm stand in the Hamptons

Check out American craft furniture at Pritam and Eames in East Hampton and, for classic Hamptons beach style,Hildreths in Southampton.

Visit the Parrish Art Museum’s brand new space in Watermill, designed by New York World Trade Center architects Herzog & de Meuron, to see work by American Impressionist William Merritt Chase plus artists who call/ed the Hamptons home including Jackson Pollock, Willem de Kooning, Roy Lichtenstein, and Eric Fischl.

Visit Jackson Pollock’s house and studio in The Springs and see where Blue Poles was created.

Watch the latest exploits of some of New York’s finest writers, actors, musicians and artists at East Hampton’s Guild Hall.

Get down at the funky Stephen Talkhouse in Amagansett renowned for its live soul and blues, rock and reggae and where the likes of Mose Alison, Billy Joel, and Patty Smith have dropped in to play.



East Hampton

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East Hampton 40.963434, -72.184801

Sue Gough Henly

Sue Gough Henly is award-winning travel writer and photographer whose bi-line has appeared in The New York Times, Travel & Leisure, The Guardian, The Toronto Star and all the major Australian publications. Her travel blog, Genuine Journeys, is full of insider tips on the best places for authentic experiences and luxury splurges. She is also the author of Australia’s Best Places travel app. When she doesn’t have sand between her toes or a pack on her back, she writes about food, wine and culture.

3 comments to How to Weekend in the Hamptons: where to stay and what to do

  • will stanton  says:

    I’ve always wanted to visit the Hamptons but never known how to figure out where to stay just for the weekend. This blog post is a real help. Thanks!

    • Sue Gough Henly  says:

      I’m glad you found this post helpful. It really is possible to have a marvellous time in the Hamptons even if just for the weekend. I’m happy I could show you how!

    • Sue Gough Henly  says:

      I’m pleased you found it helpful. It really is possible to have a wonderful time in the Hamptons even if just for the weekend.

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