Looking for the perfect East End or North Fork getaway? Long Island is full of boutique hotels and reimagined inns that balance vintage character with modern luxury. Once modest motels or historic Victorian homes, these properties have been transformed into destinations that celebrate design, hospitality, and a sense of place. Here are seven stays where history meets style.
Daunt’s Albatross
A Montauk icon since the 1970s, Daunt’s Albatross offers 24 rooms with a coastal-modern feel—think custom woodwork, vintage textiles, and natural stone. Guests can relax by the pool, fire up the BBQ, or explore Montauk on cruiser bikes. Easygoing elegance defines this family-run favorite.
Silver Sands Motel & Beach Bungalows
Retro charm meets beachfront bliss at Silver Sands, where motel rooms, cozy bungalows, and beach houses sit steps from a private beach. The on-site diner, Nookies, adds a playful touch with house-smoked fish and biscuits. Guided oyster tours and complimentary bikes make exploring the North Fork even better.
Hotel Moraine
Perched on a glacial ridge, Hotel Moraine blends elevated design with laid-back comfort. The 20 rooms feature fireplaces, terraces, and access to a heated saltwater pool. Families will love the ice cream socials, while couples can sip wine by the fire after vineyard visits.
The Lin Beach House
This restored Victorian exudes moody charm with soaring ceilings, clawfoot tubs, and chic fixtures. The six-room boutique stay is paired with a cocktail bar, Days Like These, which highlights spirits from Matchbook Distilling Co. Guests can join gin-making workshops, tastings, and seasonal dinners for a truly curated experience.
Aqua Beach Hotel
An adults-only retreat on Peconic Bay, Aqua Beach is the definition of serenity. Beachside saunas, garden Jacuzzis, and in-room massages set the tone. Guests enjoy picnic breakfast baskets and can rent kayaks or paddleboards for exploring the bay. Perfect for unplugging and unwinding.
Sound View
With panoramic views of the Long Island Sound, this 1950s classic has been reinvented with 60 cedar-paneled rooms and private decks. The Halyard restaurant serves fresh seafood, while piano nights and beachfront lounging offer that quintessential barefoot luxury Greenport is known for.
The Chequit Hotel
First opened in 1872, The Chequit has been refreshed with breezy, modern design while keeping its Victorian charm intact. Guests can sip cocktails at The Tavern, browse the on-site boutique, or enjoy farm-to-table dining before strolling Shelter Island’s quaint streets and beaches.
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