The Chequit Inn



To what began as a simple religious retreat perched atop a knoll in the picturesque historic district of Shelter Island in 1872, today gives way to a re-imagined, cozy 37 room retreat known as The Chequit Inn. The Inn still holds many of its original charms after months of restorations and renovations. The end result is a design that is relaxed and effortless yet meticulously executed. The cozy lobby and large covered porch overlooking Dering Harbor is the perfect spot for a morning breakfast or a late afternoon cocktail. The inn’s hallways call for hushed tones with their dark painted, wainscoted walls and subtle lighting, and the rooms, painted in muted tones of pink, grey and white are breezy and cool. It’s the details we love, breakfast served in bed, Turkish throw rugs, Bigelow and Further bath products and power outlets next to each side of the bed so your gadgets can charge while you sleep. Add a grab and go café called White Hill, serving Jack’s Stir Brew coffees and other tasty treats from Baked in Red Hook Brooklyn labeled “Baked at Salt”, a restaurant aptly named for the shade tree out front, Red Maple, offering both small and large plates, and a local surf and skate shop called Wampum for your surfer chic accessories to the mix and now you know why this is one of our top picks for places to stay this summer.

23 Grand Ave |  Shelter Island Heights | 631-749-0018 | website

Jedediah Hawkins Inn

PHOTOS VIA JEDEDIAH HAWKINSThe Jedediah Hawkins Inn occupies what once was the home of Jedediah Hawkins built during the Civil War in 1863. Driving up the driveway you can begin to imagine what it might have once been and once entering through the doors you know you’ve arrived someplace very special. Check in to one of 6 rooms, each with their own unique design including fireplace, AC, wireless, flat screen TV, Frette linens and Malin + Goez products. For a very unique experience book yourself into the Belvedere Suite which occupies the top three floors of this Victorian mansion, complete with its own private belvedere for stargazing for two.

Room Rates $250-$600

Best Rooms The Cider Room, Cocoa Room and Belvedere Suite


400 South Jamesport Ave | Jamesport | 631.722.2900 |

The Fordham House

PHOTOS BY DAVID KORCHINThis stately home, conveniently located on the edge of the village in Greenport, was built in 1901 by master shipbuilder H. Fletcher Fordham. The Fordham House retains many of its original details like hand carved woodwork, stained glass windows, even a vintage pull chain loo, all gracefully mixed with modern amenities. Each of the three rooms are generous in size, furnished with either a cozy chaise or over stuffed club chair, queen size beds with plush bedding, central air, wifi and docking stations. Rise to breakfast served each morning of freshly squeezed juice, local farm fresh eggs and fresh roasted coffee served either inside or out on the veranda. This comfortable, gracious home allows you ample space to simply relax or if you’d like, grab a mallet for a game of croquet out on the lawn.

Room Rates $250 - $375

Best Room The largest room with its chaise lounge, chandelier and ballroom sized bath.


817 Main Street | Greenport | 631.477.8998 |

Shelter Island House



Shelter Island House is a welcoming retreat located on a quiet lane on Shelter Island. The house, dating back to the 1800's, is beautifully restored and houses 8 tastefully decorated rooms all done in soft muted tones. All are equipped with modern amenities to make you feel right at home like a well stocked mini bar, LCD TV, free Wi-Fi and iPod docking station. There's an on site bakery plus restaurant serving up house specialties year round. Add on a fireside bar, complimentary bikes, pétanque courts and a pool making this the top pick when staying on Shelter Island.

Room Rates $225- $525

Best Room Room No. 8, which has a king-size bed, sofa and giant bathroom with Jacuzzi tub.

11 Stearns Point Road | Shelter Island | 631.749.1633 |

Harborfront Inn

PHOTOS BY DAVID KORCHIN & JONI RENTZFor those who break out in hives at the thought of sharing breakfast with complete strangers and all else that comes with staying at a B&B there's an alternative. The Harborfront Inn located right in the village of Greenport. The rooms are clean but spare, great for you non B&B types, but what it lacks in charm it makes up for with its amazing views of Greenport Harbor and the Peconic Bay. The 35 rooms, most with balconies, feature Frette bed linens and robes and amazing glass enclosure showers with massaging body sprays coming at you from all angles. The Terrace Suite, located on the third floor, offers a king-sized bed, separate living room and Jacuzzi tub. But the pièce de résistance is the private 1,000 square foot terrace, complete with lounge chairs and panoramic views.

Room Rates $299-$759

Best Room The Junior Suite with private balcony and unobstructed views of Peconic Bay and Shelter Island or break the bank and go for the Terrace Suite.


209 Front Street | Greenport | 631.477.0707 |

Shinn Estate Farmhouse

The Shinn Estate Farmhouse is conveniently located on the Shinn Estate Vineyard. The idyllic 1880’s farmhouse is not your typical B&B. Cozy and chic, each room is beautifully appointed and decorated in either earth or jewel tones offering beautiful views of either farmland or vineyard.  All rooms have private baths along with modern amenities like flat-screen TVs.

Check into this B&B through the vineyard tasting room. Once settled make yourself at home in the cozy sitting room and enjoy a glass of Shinn Merlot while thumbing through the hundreds of cookbooks lining the farmhouse’s bookshelves. Owners David Page and Barbara Shinn are no strangers to culinary know-how, being the once owners of Home restaurant in Manhattan. Wake up to a hearty breakfast, served at a large communal farm table. Orange and cranberry scones, Crescent Farm duck adobo, corn pudding, soft scrambled eggs in a whole wheat tortilla. Paired with freshly brewed coffee and a fresh fruit smoothie. No better way to start the day.

Room Rates  $289.

Best Room  Vineyard West. Cedar paneled cathedral ceiling along with a beautiful view of the vineyard.


200 Oregon Road | Mattituck | 631.804.0367 |

Morning Glory Bed & Breakfast: CLOSED


The Morning Glory is a charming, restored farm-style home on the edge of town in Greenport. Snuggle in to one of three beautifully decorated rooms of white, beige and taupe with overstuffed feather-beds and tons of fluffy, luxurious pillows. It's like walking into a 4-star hotel. All rooms have private baths and modern amenities like flat screen TVs and DVD players. You’ll be greeted by innkeepers Klaus and Renate Wilhelm who are both welcoming and knowledgeable on all the North Fork has to offer.

Breakfast is served in their elegant dining room filled with a collection of silver and porcelain. Fresh fruit, croissants, farm fresh scrambled eggs, bacon and sausage are served. But be sure to save room for Renate’s famous German pancake. 

Room Rates  $225-$320

Best Room  “Love Deeply” with its king size four poster bed and cozy sitting area.


912 Main Street | Greenport | 631.477.3324 |

Some Other Favorites

The North Fork Table & Inn | Perfect for food lovers. Located above the highly acclaimed restaurant of the same name, the four rooms here are simple and elegant. Each has a queen size bed, private bath, flat panel TV with cable and wireless internet access. Continental breakfast included. Room Rates start at $250. Reservations 631.765.0177 | 57225 Main Road | Southold |

The Orient Inn | Back to nature. An arts and crafts, turn of the century home offers five airy and spacious rooms all with private baths. Large, cozy living areas on the main floor. A full breakfast is served daily in the dining room or on the front porch. Easy on-line booking. Room Rates start at $245. Reservations 631.323.2300 | 25-500 Main Road | Orient |