What It's Really Like to Stay at the Chicest Hotel on Nantucket

What It's Really Like to Stay at the Chicest Hotel on Nantucket originally appeared on Parade.

It's not often a place makes you feel both foreign and right at home, but that's exactly what it's like stepping into the lobby at The Greydon House—and that's very much by design. Inspired by Nantucket's seafaring past and prosperous whaling trade, the boutique hotel (named after a diminutive version of Nantucket's nickname, The Grey Lady), distills everything that's so special about Nantucket in one perfectly curated experience. From its wood-plank-lined rooms and cozy bar to its eclectic artwork and globally inspired plantings, every detail tells a story, and it's one of adventure, art and subtle luxury that attracts those far and wide to Nantucket's weathered, yet buzzing shores. Located across the street from The Whaling Museum, it feels like the hotel took inspiration from the museum itself, blending centuries of history and a global sensibility. It somehow manages to feel like a weathered captain’s house and a Brooklyn art curator’s pied-à-terre all at once. When I learned the design firm behind it also created the Ace Hotels in New York—places I spent years frequenting while working on my own projects—it made sense. That lived-in ethos, the sense of creativity and history—are hallmarks. (Gwyneth Paltrow is a fan.) Here’s everything you need to know about staying at the chicest hotel on Nantucket.

Related: A Beginner's Guide to Nantucket

The Hotel: Coastal Lived-In Inn Meets Euro Boutique Cool

Even though there’s no connection to Vanity Fair’s Graydon Carter, you could be forgiven for thinking so. Every detail—from the abstract art by contemporary American artist and printmaker Terry Winters to the Euro-style room keys behind the desk—feels like it's pulled from the pages of a magazine.

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The living-room-style bar is pure '70s-den-meets-mariner's-library, with velvet flame-patterned sofas, perfectly crowded gallery walls and wool ship paintings that feel lovingly plucked from a grandfather’s attic. The backbar was sourced from a New York City general store; the top was custom-built. The mural behind the bar, depicting an 1800s Chinese port scene, nods to Nantucket’s history and trade routes and was inspired by pieces in the North Shore's Peabody Essex Museum.

The Rooms: Global Details With Local Charm

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Every room is planked in creamy white wood and bathed in soft, glowing light. It's here the sense of place is felt the most—as if the ghost of the original sea captain owner is still in the bones of the Federal-style details. Custom-designed beds with John Robshaw bedding and Indian block-print linens evoke Eastern trading routes; Moroccan-style inlaid furniture and handcrafted Portuguese bathroom tiles tell the story of the global reach the island once held. Vintage phones and curated curios round out the lived-in look without any fussiness.

Related: 17 Things to Do In Cape Cod's Most Charming Town

Via Mare Restaurant: Venetian Tapas With Global Flavor

Technically separate from the hotel,Via Mare still feels like its soulful sibling. With plush velvet banquettes, sea-blue walls and oil paintings that wouldn’t feel out of place in an old Venetian villa, the space invites you to stay awhile.

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We had every intention of hitting the bar afterward—but ended up spending hours lingering over tapas-style small plates instead: octopus charred to perfection, crisped sunchokes, caviar-topped pancakes and spicy cumin lamb with tingly sichuan peppercorn. Dishes come as they’re ready, lending a European rhythm to the meal—and the conversation. There's a whimsical selection of cocktails and the Michelin-starred-chef-driven menu has a a clear love for spice and unexpected pairings.

The Vibe: Sophisticated and Steps From the Best of Nantucket

One of the biggest perks? Its location. Just off Broad and Federal Street, a 10-minute walk from the wharf, across from the Whaling Museum, it's right down town—but removed enough that you’re not woken up by nightlife. It’s the kind of spot your most in-the-know friend would book. It's a perfect spot for wedding parties or out-of-town guests.

Even on a rainy April night, the bar buzzed with stylish locals and guests—a sign of a place that has real staying power (SNL players and Bill Belichick have been known to post up). It’s the kind of space where you could imagine dreaming up your next novel, bonding with the bartender over obscure spirits or just playing a game of backgammon by candlelight.

Unexpected Perks That Made My Stay Even Better

The 20-room property may be small, but it’s filled with gestures that make you feel looked after:

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Fujifilm Instax cameras available for guest use

Le Labo and Grown Alchemist products in the bathrooms

Lands’ End beach totes, towels and flipflops for nearby Jetty Beach

Optional private, 3-hour sailboat charters, complete with lobster rolls and rosé

What Visitors Say

Guests have a lot to say about the rooms, highlighting: "each room is unique and quiet," and "We had three rooms on the front, side and back and we all slept like lambs" comments one on Trip Advisor. Another says, "Petite Queen Number 21 is perfect for the solo traveler."

Guests mentioned some things to know before you go, suggesting that you should "plan to park and walk to the hotel, and there isn't a commisary, so bring water, Tylennol, etc."

Most rooms don't accomodate pets, but the two private rooms with street entrances do. "Perfect room if staying with a pup," said one commenter.

If You Go

Best time to visit: Late spring and early fall offer seasonal deals.

Booking tip: Weekday stays are quieter; book early for summer weekends. Commenters said to ask for Room 16 if available.

Travel tip: Arrive early to the Ferry to grab a seat on the top deck for prime Brandt Point Lighthouse and golden-hour sunset views.

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Visit greydonhouse.com to find available dates and book.

Related: 11 Can’t-Miss Things to Do on Cape Cod, According to a Local Travel Expert

What It's Really Like to Stay at the Chicest Hotel on Nantucket first appeared on Parade on Jul 5, 2025

This story was originally reported by Parade on Jul 5, 2025, where it first appeared.