Hotel Insider: Quiet Charm at Shelter Island’s The Chequit
The Chequit opened its doors on May 8, and is a luxurious getaway. (Photo: The Chequit)
The Hotel: The Chequit
The Location: Just a 5-minute walk from the Island’s North Ferry, the recently revamped 19th century hotel is in the center of the Heights Historic District in sleepy Shelter Island, New York. The seriously charming — but small — neighborhood boasts cute shops, delicious restaurants, and Victorian gingerbread houses.
The Backstory: Shelter Island is known for being sleepy and laid-back — the opposite of the see-and-be-seen, Manhattan-transplanted-to-the-beach scene of the Hamptons. The one exception to the calm on the island is Sunset Beach, the Andre Balazs owned hotel that attracts the glamorous-crowd in droves. When it was announced that the beloved, chintz-infused Chequit would be revamped with new owners this year, locals were worried they would have another raucous playground (especially since co-owner David Bowd was previously COO for Balazs Properties). However, once the hotel quietly opened up this summer, it was clear that the hotel aims to be a more serene retreat. It’s the perfect year-round addition to the island.
The lobby at Hotel Chequit. (Photo: The Chequit)
First Impressions: Gone is the Victorian-era property’s chintz wallpaper, replaced with a crisp, almost urban palette. Think grey and pink colorblocked walls in the guest rooms and canary yellow and grey upholstery in the sitting room/living room. Beyond the hotel’s shop selling Wampum surf T’s, and Turkish beach towels in the guest rooms, the design feels less beachy and more suited for a cozy year-round escape.
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The Property: Designer and co-owner Kevin O’Shea did a lovely job with the Chequit’s 37-rooms which are spread out over three buildings. There’s the main building and a cottage across the street that feature rooms done in a similar style — handwoven rugs, pink and gray walls, roomy tubs, and divine beds (if ever there was a heavenly bed this is it). Many rooms feature iron daybeds that double as an extra bed.
A daybed seating area and plush custom king bed in the Chequit suite. (Photo: The Chequit)
If you can swing it, The Terrace Suite with its pillow-laden swing and strung lights hung across the space — is magical. The Summer House offers a way more casual vibe with whitewashed walls, iron beds, and vintage art. The Summer House building while cute, is not fancy at all, so it’s best for those looking for fun charm and a deal (rooms start at $195), not those looking for posher accommodations.
Perk for non-drivers: With the hotel walking distance from the ferry, and a prime position in town, city dwellers can easily have a country escape without needing a car. In addition to the hotel’s yummy Red Maple restaurant serving up seasonal New England fare, there are two year-round restaurants, a café, and a small market in town. The Heights also boasts a pilates studio, a chic clothing store Marie Eiffel, and a drugstore with a vintage diner.
The perfect place to relax on a quiet afternoon. (Photo: The Chequit)
What I loved: One of the reasons the hotel has such a serene sensibility, is that with the exception of the bar and restaurant, all the spaces in the hotel are reserved for guests. It’s a smart move, because without a doubt the delightful terrace and the cozy living space would be packed. It’s motivation to check in.
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What I didn’t love: To be honest, it’s hard to come up with any negatives. The staff was warm and accommodating (and endlessly patient with high-maintenance guests). My only thought is that if you are looking for a Hamptons scene, this isn’t going to be your spot. It’s quiet and designed to be an escape. While I loved that aspect, it’s not for everyone. Another small grievance would be that it would be lovely to have check out be at noon rather than 11 a.m.
The Red Maple restaurant has a seasonally inspired New American menu. (Photo: The Chequit)
Who it’s best for: While it is definitely suited for adults, I checked in with my (lively) kids ages 10 and 3. The staff could not have been more accommodating. With most rooms featuring daybeds, it’s an easy fit for a family of three. They added a high air mattress to accommodate 4. Even staying in the entry-level room, a Cottage King could easily accommodate the group. The kids loved having meals on the terrace (rocking chairs were a plus), and the café right downstairs. That being said, there aren’t any kid bells and whistles (game rooms etc.), so it’s best for a family that is eager to explore the island past the hotel.
What’s Not to Miss: While it’s warm enough this fall, the lovely covered porch/terrace is heavenly during the day or night. Vintage furniture piled with colorful pillows include multiple chairs, daybeds, sofas, and rocking chairs to relax in. Enjoy the complimentary breakfast spread (frittatas, homemade granola, fresh fruit, yogurt parfaits, and muffins) while taking in the water view. Sip wine there in the evening, or bring up your dinner from Red Maple. It’s guest-only so it’s never crowded — a huge perk. Once it gets cold, transfer all the above activities to the living area and the fireplace.
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