Looking for a Last-Minute Labor Day Getaway? This Boutique Hotel Was Half the Price of My Go-To Hamptons Stays

Located in the heart of Greenport Village, The Harbor Front Inn is a boutique waterfront property that feels like a well-kept secret. Right off the bat, the lobby strikes a balance between cozy and curated: velvet club chairs in rust and mossy green, kilim ottomans, rattan lounge seating and natural fiber rugs that make you want to kick your shoes off and stay a while. The palette is earthy and muted—terracotta, driftwood, sage, and deep denim blue—with soft morning light filtering through oversized windows that overlook Greenport’s harbor.

Our king suite felt equally airy and understated: pale seafoam walls, a blue-gray ceiling, vintage-inspired brass bedside lamps and a chic little desk (which happened to be great for writing a hotel review when it started downpouring). To that end, we had a private balcony overlooking the harbor, and all the thoughtful details made a difference when the weather wasn’t ideal: plush bedding, soft lighting and blackout curtains that actually worked.

As for the extras, there’s a heated seasonal pool with bay views, daily continental breakfast and you can rent cruiser bikes (or moke!) upon request. They also loan out kite kits and Laguna Beach blankets for picnics in nearby Mitchell Park and offer author talks, art nights and other cultural programming—though we were there on an off weekend. Bonus: It’s pet-friendly, with a "pawesome" package that includes a dog bed, treats and a waived fee. (Our next trip will 100 percent include my parents’ dog.)

Where to Eat

Greenport isn’t sprawling, but it’s packed with gems—all walkable from the inn. For breakfast, we grabbed bagels and coffee at Goldberg's (a staple I love from the South Fork). Then, we split a delicious buttery hot lobster roll at PORT while watching ferries pull in and out of the harbor—easily one of the most scenic lunch spots in town. 1943 Pizza Bar had thin-crust pies and margheritas under string lights—bonus points for its chic Tulum-style interior. And if you’re an ice cream person Amazing Flavors on Front Street delivers exactly what the name promises. The oatmeal cookie scoop is a must.

Dinner, though, was the star. We drove five minutes to The Halyard, inside the Sound View hotel, and ordered local oysters, a breadcrumb-loaded Caesar salad, tuna tartare toast, and a perfectly charred NY strip steak that felt indulgent but not excessive. The cocktails tasted like summer—even in a storm—and the adjacent wooden piano bar sealed it. It was the kind of scene that played right into my New Yorker roots—only with a salt breeze and zero pretension. 

While we would've loved to lounge poolside at the Harborfront all day (it has an amazing view of the water), weather wasn't on our side. So instead, we started with the obvious: walk the harbor, grab a book (or a kite), and wander through Mitchell Park, which is directly across the street. At first, we debated a rainy afternoon at the Greenport movie theater next door—an old-school staple, with popcorn that costs less than $10 and handwritten showtimes taped to the glass. It felt like being 14 again, in the best possible way.

Then of course, we eventually decided to head out to the wineries. Our favorite was Kontokosta, which offered a gorgeous view of its sprawling vineyard, crisp bubbly rosé, and a rustic-chic patio setup. Back in town, we stumbled into a few local art galleries, most of which featured work from North Fork-based painters and photographers. Then there was the vintage furniture store on Main Street (I’m still dreaming about a leather armchair I saw), where my boyfriend quite literally had to drag me out before I talked myself into strapping it to the top of my Dad’s Jeep.

There are also farm stands, tasting rooms, and tucked-away boutiques scattered throughout the area, but honestly, we could’ve spent the whole weekend doing absolutely nothing and still felt like we’d gotten away.

When I think about the Hamptons now, I mostly think about what’s been lost—charm traded for clout, bookstores for Balenciaga. But in Greenport, I found something that felt familiar in the best way: a version of Long Island that’s still a little wild around the edges. There’s no velvet rope, no valet line and no one asking what brand your beach bag is. Just cozy harbor views, down-to-earth people and a piano bar that made my New Yorker heart swoon.

After just one weekend at The Harbor Front Inn, I can officially say I’ve crossed over: consider me a North Fork convert. Not to mention that, unlike so many South Fork stays, it won’t drain your savings account. I’ve stayed at the Sea Crest in Amagansett for years—where prices can hit $600+ per night during peak season—and this was not only cleaner and quainter, but came in at $330 for a last-minute Memorial Day weekend booking. A rare gem: charming and financially sane.