Revamped Victorian inn


Slow-mo Shelter Island

The Chequit is a restored 19th-century clapboard-clad inn, set in a serene harbourside hamlet on Shelter Island. The rooms are subtly styled in pastel pink and grey, with Native American patterned rugs on the floor and Turkish towels hanging from rustic ladders next to the claw-foot bath tubs. The vintage-print veranda daybeds are all set for a snooze, but don’t forget to explore the island too; there are clearwater coves for kayaking, nature trails for hiking and country lanes for biking. A wholesome breakfast is included, and in the evenings signature cocktails flow at the bar and dinner is served around the wise old maple tree in the garden.

Smith Extra

Get this when you book through us:

A bottle of wine in your room, or over dinner at Red Maple


Photos The Chequit facilities

Need to know


36, including 6 suites.


11am. Earliest check-in, 4pm, but flexible, subject to availability.


The building dates back to 1872, and was converted from a Methodist community hall into a hotel in 1874. In its 1960s heyday, the likes of Marilyn Monroe and the Kennedy family stayed here, but it later fell into a state that was a bit… err… shabby-without-the-chic. David Bowd and Kevin O’Shea (head honchos of the Salt Hotels minigroup) came to the rescue in 2014. They restored the building to the lofty standards of their Provincetown boutique hotels – Salt House Inn and Eben House – and they’ve since repeated the trick at The Asbury in New Jersey.

Hotel closed

Annually on Thanksgiving and Christmas days. From November 2017 to March 2018, the hotel will only be open on Fridays and Saturdays.

At the hotel

Café, car park. In rooms: Free WiFi, air-conditioning, minibar, free bottled water, C.O. Bigelow bath products.

Our favourite rooms

The Garden Suite boasts two bathrooms and is flooded with light from its large bay window; outside, it has a private terrace with a table and sofa built for two. The bedroom in the Loft has a claw-foot bath tub under its vaulted ceiling, almost splashing distance from the king-size bed.

Packing tips

Boots and binoculars if hiking in the Mashomack Preserve is your bag. If not, a straw sunhat and a good book – John Steinbeck lived across the water at Sag Harbor, and his Travels with Charley begins with a trip to Shelter Island.


The hotel’s White Hill Café has you covered for stir-brew coffee, sweet treats from Brooklyn-based Baked, and grab-and-go picnics for the beach.


All ages are welcome. Most rooms have space for a travel cot, but it’s best to check when you book. Highchairs are available in the restaurant.

Food and Drink

Photos The Chequit food and drink

Top Table

On sunny summer days, there’s no beating a table under the maple tree on the front lawn.

Dress Code

Anything at ease, and that includes shorts, t-shirts and those shoes you only really wear on holiday.

Hotel restaurant

The dinner and Sunday brunch menus at Red Maple feature American favourites expertly crafted by chef Gayle Scarberry using seasonal local produce. There’s market-fresh fish every day, and the Red Maple burger is the signature pick for carnivores. Veggies are well-looked-after too, with homestyle mac ‘n’ cheese and portobello mushroom with quinoa and goats’ cheese. Brunch is wholesome and hearty – think syrup-soaked pancakes and fillet-steak eggs Benedict. Inside, the restaurant has dark-wood floorboards, statement wallpaper and vintage furniture. Out on the lawn, tables and chairs are clustered around the mighty maple tree, and light bulbs are strung between old-world lamp posts. 


Hotel bar

The Red Maple bar shakes up its own takes on classic cocktails; try the punchy Ginger Cosmopolitan or Red Maple Margarita. The reception desk moonlights as the Lobby Bar each evening, serving a selection of wines by the glass and bottle. 

Last orders

Breakfast is from 8am until 10.30am. Red Maple is open for dinner and drinks from 5pm to 10pm; brunch is on Sundays only, from 10am to 3pm. The Lobby Bar serves drinks from 4pm until 9pm.

Room service

For breakfast-in-bed, just ask.


Photos The Chequit location
The Chequit
23 Grand Ave
Shelter Island Heights
Shelter Island Heights
United States


New York’s JFK airport is the largest international hub, and it’s actually on Long Island, between the city and the Chequit – it takes just under an hour to drive from the airport to the hotel. Many major airlines also fly into LaGuardia airport (also on Long Island) and Newark airport, which is on the other side of the city.


From New York, take the Long Island Railroad from Penn Station to Greenport (the journey takes two and a half hours), then cross the street and hop on the North Ferry to Shelter Island. If you’re coming straight from JFK, all trains stop at Jamaica station, next to the airport.


If you plan on exploring Shelter Island and the Hamptons nearby, a car will come in handy. The area is well-connected to New York (a three-hour drive away), and the ferries to Shelter Island take cars as well as foot passengers. The best deals on car hire are usually at New York’s airports, rather than in the city. The Chequit has its own car park, which is free to use during your stay.


The little boat trip is part of the charm on any trip to Shelter Island. There are two crossings, each taking just a few minutes: the North Ferry from Greenport docks just down the hill from the Chequit, while the South Ferry links the other side of the island with the Hamptons. For longer-distance roadtrippers headed north to Boston and beyond, there’s the nifty Cross Sound Ferry from nearby Orient Point to New London in Connecticut, which cuts out the drive back down Long Island.

Worth getting out of bed for

The best of the beaches are: Hay Beach for sweeping views of Gardiners Bay and Bug Light Lighthouse; Shell Beach for activities including kite-surfing and paddleboarding; Crescent Beach for pink-tinged sunsets and an excuse for cocktails at Smith-approved Sunset Beach hotel. Stop by Picozzi’s bike shop and pick up a two-wheeler for a day of island-exploring; the roads are almost all yours and energy-sapping hills are mercifully few and far between. Or, ask the hotel to book you an activity nearby: golf, fishing, sailing and kayaking are some of the most popular. Mashomack Preserve nature reserve draws hikers, bumpkins and birdwatchers to its wetland trails. Check the concert schedule at the Perlman Music Program, an academy for string musicians run by renowned violinist Itzhak Perlman. The Hamptons are just over the water on Long Island; Sag Harbor, Southampton and East Hampton are the places to see and be seen.


Local restaurants

Follow the winding road inland to Vine Street Café, a quaint cottage restaurant serving high-grade American classics made with produce straight from local farmers and fishermen. Modern trattoria 18 Bay, on North Ferry Road, is something of a Shelter Island institution. The four-course set menu changes weekly, but is always Italian-inspired, including an antipasti quartet and handmade pasta.


Local cafés

Down by the harbour, Marie Eiffel Market is Shelter Island’s own little piece of Paris. The breads and pastries are baked in-house, and the artisan cheese selection is the star of the gourmet-grocery show at the deli. The lobster roll is small but oh-so-perfectly formed, and the best spot to enjoy it is out the back on the over-water decking.


Local bars

For DJ-sets and seaside cocktails with the hip Hamptons crowd, head to Sunset Beach hotel. Salt is a buzzy dockside bar and grill on the south side of the island; try the house beer or signature Dark ‘n’ Stormy.



Photos The Chequit reviews

Anonymous review

Every hotel featured is visited personally by members of our team, given the Smith seal of approval, and then anonymously reviewed. As soon as our reviewers have returned from this boutique hotel in Suffolk County and unpacked their souvenir clam shells and beach pebbles, a full account of their waterside break will be with you. In the meantime, to whet your wanderlust, here's a quick peek inside the Chequit on Shelter Island…

This is what a stay at boutique hotel the Chequit is all about: a little provincial ferry chugs across the sparkling channel from Long Island, drops you at the village harbour, and after a walk along a sun-dappled lane, you reach a Victorian-era white-clapboard inn overlooking storybook boats bobbing in the bay. Each morning, take your breakfast in bed or on the veranda, and then set off to explore the island by bike, kayak or just on your own two feet. One day, grab bait and tackle and cast a line into the gently lapping waves – if you’re lucky you’ll catch a weakfish, or chequit (‘chee-kwit’), as the local Native American tribe used to say. In the evening, clink signature house cocktails at the bar, and pick a table for dinner under the mighty maple tree in the garden. The hotel may be just across the water from the glitzy hedonism of the Hamptons, but the Chequit on Shelter Island has a charm all of its own.

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