Another Side of the Hamptons

At The Penny Lane Hotel, the Hamptons feels a little more relaxed, and a lot more local.

By Lisa Loverro

Tucked along a quiet waterfront in Hampton Bays, The Penny Lane, an intimate 18-room hotel offers a more relaxed alternative to the sceneier enclaves farther east. Just about two hours from New York City, The Penny Lane sits on Penny Pond, between Shinnecock Bay, Peconic Bay and the Atlantic Ocean, putting water, beaches and the laid-back rhythm of the East End within easy reach.

I stumbled upon the property while searching for a boutique stay a little closer to New York City. I’ve been a frequent visitor to the East End for years, with Amagansett serving as my summer retreat for many of them. But when looking for a quick escape, I’d rather not spend hours battling the traffic and making the long drive out east.

The property is a thoughtful reimagining of the former Drake Inn, a classic 1960s motor inn overlooking the canal. Today, Lark Hotels has given it a fresh, beachy sensibility while preserving some of that old-school Hampton Bays charm. The result feels intentionally unfussy: a place where you can spend a lazy afternoon by the ocean, take a dip in the pool, or borrow one of the complimentary bikes for a leisurely ride around town. And mornings start easily here. In addition to their complimentary breakfast, you can walk over to Hampton Coffee Company for an early cup of coffee. Add a sandy waterfront along the canal and a warm, attentive staff committed to making guests feel welcome, and The Penny Lane strikes just the right balance between relaxed and refined.

Accommodations range from Queens and Main House Kings to a Waterview King Suite and two-bedroom suites, making the hotel appealing to both couples looking for a weekend escape and families or friends traveling together. Rooms combine coastal simplicity with modern conveniences, including mini refrigerators, coffee stations, and smart TVs along with “Lather” bath products, and plush bedding.  

Perhaps most appealing is the property’s commitment to being a little gentler on its surroundings. Solar panels help power the hotel, while sustainable products and filtered water throughout the property reduce the need for disposable plastic bottles. Complimentary bicycles encourage guests to leave the car behind and explore the neighborhood on two wheels. It’s a fitting approach for a hotel surrounded by so much natural beauty: sustainability here feels less like a slogan and more like part of the everyday experience.

And then there’s Hampton Bays itself. Rather than having to venture far for dinner, guests can settle into the local scene. For a casual meal with a distinctly waterfront feel, take a walk over to the Station Bar, offering the quintessential local bar-and-grill experience, or quick drive to Whales Tale – Hampton Bays, a neighborhood favorite (try the Bang Bang shrimp). Both make it easy to trade the polished restaurant scene for something more relaxed and decidedly local.

The Penny Lane delivers the Hamptons without requiring the Hamptons performance: no need to dress for the occasion, chase reservations or keep up with the crowds. Instead, there are bikes, beaches, boat docks, sunsets and a poolside afternoon waiting to happen. For travelers seeking a slower, more authentic East End escape, the property makes a compelling case for Hampton Bays.