6 Best Hotels in Greenport, Long Island

Deep red walls, antique furnishings, oversized mirrors, and chandeliers make this classic Victorian home a little bit eclectic and a little bit sexy, and place it in a class of its own. The owner—a California transplant who visited Greenport several years ago and loved it so much that she never left—will always welcome you with open arms. It's got a great porch on which you can enjoy a bottle of local wine or beer from the neighboring Greenport Brewery. It's also just steps away from Main Street shops and restaurants. Breakfast includes local farm eggs and vegetarian and vegan options. By design, rooms don't have TVs to allow guests here a true retreat and digital decompression.

Minutes from the Long Island Sound, world-class golf courses, vineyards, and restaurants, this reasonably-priced North Fork inn features a main house and a few nearby properties including family-friendly efficiencies. A lovely Victorian house has three simple but nicely-appointed suites and four efficiencies, further efficiencies out back have fully-stocked kitchenettes, there's a cottage with two bedrooms, and an apartment that sleeps five and has a porch overlooking the neighboring lavender farm. They all share the outdoor pool and picnic area, making it a popular choice for families.

This hotel more than ably demonstrates how an inspired touch can really transform a 1950s motel into a sleek, minimalist lodging—and it's not just down to the cool, modern color scheme. Rooms are spacious, with light-wood platform beds, graphic rugs, and metal accents, and bathrooms are large and right up to date. a block from the waterfront. Cuvee is the on-site farm-to-table restaurant and bar, open in high season for dinner Thursday–Sunday and brunch Friday–Sunday. There's an outdoor pool.

Attracting a high-end clientele, including city dwellers seeking a luxury North Fork getaway, most rooms at this three-story, gray-and-white inn have balconies, some with harbor views. All rooms have high-speed Internet access and flat-screen TVs. Interiors are contemporary and bright, with cherrywood furniture, leather armchairs, and light-color carpeting. Down comforters and Frette linens outfit the beds. For a really big splurge, you might consider the Terrace Suite; at 800 square feet, it's double the size of the regular rooms, and it has a 1,000-square-foot deck.

Here it's all about location—each room in this complex of motel-style buildings has a deck right on the 1,400-foot-long private beach. Interiors, although simple and in need of some updating, are clean and bright. The staff is friendly and accommodating. An outdoor pool, sport courts, and a small fitness room are all on-site.

Built in 1880, this green-certified bed and breakfast is in a good, central location by the water, and just steps from Mitchell Park and the Main Street shops, restaurants, and museums. You can take the train from the city for a quick getaway, and would only need a car for exploring beyond Greenport. Breakfasts are copious, and include home-baked breads, free-range eggs, and treats such as German apple pancakes with raspberry coulis. Each generously appointed room has ensuite bathroom, a flat-screen TV, and free Wi-Fi. Ask about the Vine Time Wine Getaway special.