Hotel Stays: The Roundtree, Amagansett
I’ll be honest: I’ve never been a fan of the Hamptons. To be fair, I’ve only been a few times—and only in summer. I’ve visited the North Fork many times throughout the year, and I love going upstate.
Between the overcrowding and the overpricing, the Hamptons never held much appeal for me. Until I went in February.
February is one of my least favorite months. The weather is terrible. (And yes, it snowed the night before we had to drive home, but thanks to plenty of snowplows—both on the main road and at the hotel—that became a nonissue, thankfully.)
Winter in the Hamptons is a different experience. This is when locals settle in, and travelers looking for a quieter weekend have their moment. Many restaurants and bars shut down for the season, but hotel rates drop, and it’s easier to get a reservation at the spots that remain open.
Amagansett sits comfortably between Southampton, Bridgehampton, and East Hampton to the west and Montauk to the east on the southern coast of Long Island.
The Roundtree, part of the Small Luxury Hotels collection, is a fully restored boutique hotel open year-round. Both family- and pet-friendly, the homestead-style retreat has 14 accommodations, including cottages, barn rooms, and suites in the main house, plus a meticulously decorated beach house once owned by playwright Neil Simon.
Since this is a pet travel blog, I have to emphasize just how pet-friendly this place is. The Roundtree had been recommended to me for years, but I hadn’t made it there until now. My only regret is waiting so long. We all had a wonderful time—especially Dash. He was treated like royalty, starting with a new toy at check-in.
A bone chew toy waited in the cottage kitchen, along with Yeti food and water bowls and an oversized dog bed. (Not that he needed it—Dash loves a couch, and there were three. He sampled them all, but our bed won in the end.)
By luck—likely a low-occupancy weekend—we were upgraded to the front house, a two-bedroom, two-story cottage. One funny thing about staying there: People mistake it for reception, even though a sign directs them to the actual office down the driveway. If you stay there, keep the deadbolt on—someone will walk in by accident.
It was fun pretending to be homeowners for the weekend, though running up and down the stairs constantly felt like a bit much. Sometimes, too much space really is too much.
Except for the kitchen. A kitchen can never be too big, and this one was glorious, with cleverly hidden drawers and Miele appliances. It was also fully stocked. After a stop at Amber Waves Farm, Market & Cafe—because three hours in traffic getting out of New York City left us starving—we ate like civilized people on CB2 dishware.
A bottle of Bordeaux was waiting for us, along with curated snacks, Saratoga bottled water (still and sparkling), sodas (Coke, Diet Coke, ginger ale), and Harney & Sons bottled peach tea. All of it was included and replenished throughout our stay. A gourmet breakfast of yogurt parfaits and local pastries (do not skip the everything bagel) was delivered to our room daily. Laundry service was also included.
In many ways, it felt like a boutique luxury all-inclusive. The stay wasn’t cheap, but the experience wasn’t designed to nickel-and-dime guests. Once you’re here, you’re meant to feel at home.
Parking is free—one car per cottage. A Tesla-specific charging station sits next to the front house cottage. Other EVs can charge through DC outlets, but they’re slow, gaining only 2% per hour. It’s fine for an overnight top-up, but for a real charge, I’d recommend a supercharger. We used one in Bridgehampton, approximately 10 minutes away by car, and went from 48% to nearly full in 30 minutes for under $30.
Winter guests can book in-suite wellness treatments (one of the few things not included) and enjoy fine-dining room service from Il Buco al Mare, just a few steps down the street. The hotel swaps out summer’s ice cream cart for a bonfire pit with s’mores at sundown.
Being on the main road that runs through the Hamptons—and just steps from a Hampton Jitney stop—also makes this a great home base to explore popular spots that are packed in the summer, like Wölffer Estate Vineyard for wine tasting or LongHouse Reserve for its eclectic outdoor art and sculpture garden. These places draw hundreds of visitors per day when it’s warm, but in the off-season, you can actually enjoy them rather than rush through.
All in all, my winter weekend in the Hamptons was so nice…I’m tempted to come back here in the summer—crowds, prices, and all. If it’s anything like this, it just might be worth it.
