If the North Fork is Long Island’s version of Brooklyn, then Greenport is its Williamsburg. No longer a raffish, undiscovered, locals-only spot, the formerly rundown town — once famous for shipbuilding, bootlegging and oyster processing — now attracts tourists from around the world with its polished restaurants, sophisticated wine scene and upscale shops. As befits a trendy waterside destination, Greenport is also experiencing a hostelry renaissance. Your choices are no longer limited to genteel B&Bs and questionable roadside motels on the outskirts of town. Three nifty hotels are up and running. Another, the Lin Beach House, opened in the old Shady Lady on the North Road. Although the rooms and restaurants at these places are chicly decorated, the vibe at each one is welcoming and inclusive, like friendly, low-key Greenport itself.


Credit: Randee Daddona

Stirling Square, a little U-shaped plaza off Greenport’s Main Street, was always charming. But it took the team of lawyer Bruce Pelton and fashion designer Alex Vinash, to realize its potential as the lodging-dining-shopping heart of town. Pelton purchased the property in 2014, renovating the upstairs lodgings and downstairs restaurant and renaming both after the tree that anchors the collection of buildings. Five rooms located in a former carriage house are decorated in minimalist vintage style, with whitewashed, beamed ceilings and a soothing color palette of gray, black and taupe. Each features a marble-topped kitchenette, stocked mini bar and fluffy bathrobes. A couple of larger apartments can accommodate families and small groups.

The lively restaurant, serving new American fare, offers priority reservations to guests (a must in summer). Indoor and outdoor fireplaces warm guests during the colder months. The outdoor bar, built around that beech tree, is a fun place to sample some North Fork wine or beer. An interesting but unpretentious menu includes plenty of local ingredients (Crescent Farm duck wings), crowd pleasing favorites (buttermilk fried chicken) and forays into the exotic (fish in mushroom dashi). 

Credit: Randee Daddona

The hotel reception area doubles as a showcase for Vinash’s clothing designs. Rattan lounge chairs, boldly striped wall paper, inlaid tile floor and banana trees in pots make the space a playful place to try on a feathered miniskirt. 

WHERE 300 Main St., Greenport

INFO 631-477-6571, americanbeech.com


Credit: Randee Daddona

It’s not surprising that passers-by often enter the The Gallery Hotel under the mistaken impression that it is an actual gallery. Peek through the front windows of the 19th century shingled structure and you’ll be curious, too. The funky thrift shop-pop art décor includes furniture, lighting, paintings, maps and books from owner Carolyn Rusin’s impressive accumulation, decorating the public spaces of what is actually a 10-room boutique hotel. 

Staying here is like staying at the home of a wealthy, stylishly eccentric and hospitable friend. One delightful room leads to the next. The lobby, with its yellow and teal upholstered furniture, abstract art and potted plants, is a comfy place to plop down and page through one of the design books displayed on a midcentury modern bookcase. Breakfast (included in the price of the room) is served in the Salon, a sunny, high-ceilinged area dominated by large striped pink daybeds and French doors. Through those doors is the patio, sporting a black-and-white striped awning and furnished to the hilt for eating, drinking, and lounging during the warm weather. Back inside, there is a darkened screening room for watching old movies, and the Gallery, a sofa- and pillow-filled space that displays more of Rusin’s collections, including a vintage record player and vinyl records that guests are free to enjoy. 

Credit: Randee Daddona

This crazy country house feel has made the Gallery a frequent host of all kinds of private events, from baby showers to bachelor parties to weddings. Small parties are held in spaces that can be closed off to the public. The entire hotel can be booked throughout the year for bigger celebrations.
Snug and comfortable rooms, whitewashed and wood-beamed, are brightened with colorful artwork and accessories as well as stocked minibars. Some have decks. Two larger suites are appointed with Jacuzzis, kitchenettes and private outdoor spaces. 

Kon Tiki, a restaurant off the lobby, serves a variety of authentic Asian dishes including Peking duck, Korean short ribs and pork shumai. Naturally, the drinks menu includes exotic cocktails like the Pineapple Day Dream (tequila, pineapple juice, blood orange liqueur) served in ceramic tiki bar glasses.

WHERE 441 Main St., Greenport 

INFO 631-477-4000, galleryhotelny.com


Credit: Read McKendree

New York-based hotelier Erik Warner and his partners have transformed the Sound View, a vintage 1953 motor court just outside Greenport, into a family-friendly, design-forward beach resort. Yes, the 55 rooms and suites are still directly entered from the parking lot fronted by Route 48. But on the other side of the long, low structure is a quarter mile of private and picturesque beach. Every room has a spectacular view of the water. Each one has either a shared or private deck that gets you even closer to the Sound’s gentle waves. The rooms themselves are soothingly decorated in pared-down nautical style, with cedar shiplap on the walls, ropy navy rugs and rich burgundy bedding. 

Lounge chairs dot the decks and line the beach. A large elevated swimming pool has a water view (and a lifeguard). Bikes and kayaks are available for exploring. There’s yoga outside as well as in. 

Credit: Read McKendree

Warner is determined to make the hotel a year-round gathering place for visitors and locals. The menu at the Halyard restaurant is full of accessible classics employing local ingredients, including lobster mac-n-cheese, lobster sliders, classic fried oyster plate, and fish & chips. An atmospheric piano bar adjacent to the restaurant has featured visiting jazz artists from Joe’s Pub in Manhattan. The Library, a book-lined dining room, can accommodate private parties. Room rates start at $325/night for summer and $195/night for fall, winter and spring.

WHERE 58775 Rte. 48, Greenport 

INFO 631-477-1910, soundviewgreenport.com

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