The conveniently located boutique hotel—with enchanting interior design by Roman and Williams—offers an array of options for winter guests

Each summer, the population of Nantucket swells, roughly, to 80,000 individuals looking to bask in the island’s natural beauty and its quaint New England village environs. In the off-season, those numbers dip to 14,000. While some of the upscale shops, restaurants and bars shutter for those months—some accommodations, like Greydon House, not only remain open but schedule thoughtful programming to support guests and tap into the splendors of a destination that just so happens to be magnificent all year long. Greydon House, a boutique luxury property (that was once the home of a sea captain), embodies 20 distinct guest rooms and an intimate, elegant Venetian-inspired restaurant—all designed by Roman and Williams. Not only is the hotel conveniently located (a quick walk from the ferry), but it’s also a partner of Tradewind Aviation, which offers guests discounted private charters on their fleet of Pilatus PC-12 aircraft during the winter months.

To step into Greydon House is to understand the charm of Nantucket. An eclectic assemblage of design establishes a whimsical and enveloping environment. The warmth of natural wood complements nautically themed artworks and numerous patterned textiles. Roman and Williams struck a balance between classic and contemporary, cozy and elevated in the guest rooms and public spaces. But Greydon House is more than timeless design.

For the winter months, the hotel has looked both inward for packages and programming and across the island for partnerships on behalf of its guests—including a bike and helmet initiative with the Nantucket Chamber of Commerce. A “Long Stay Package” for bookings beyond 14 days includes unique perks like being able to check your phone at the front desk for a digital detox, and a suite of complimentary services. A collaboration with nearby Lavender Farm Wellness encompasses everything from cold plunges and massage therapy to juice cleanses and guided mindfulness meditation.

Whether heading to Nantucket to slow down or to seek out adventure in the often blustery wintertime weather, Greydon House is an enchanting place to return home.

Garison Beale—the General Manager of Greydon Hotel Group (which includes Greydon House and a series of guest houses like the standalone three-bedroom Craftsman-style property named, 52 Union, and the five-bedroom renovated farmhouse with a pool, 23 Madaket, as well as sister properties the Periwinkle Inn, Martin House Inn and Anchor Inn)—says, “I love the gray lady, our name for the fog that comes in during the off-season. It’s super-romantic and a lot of people get it. People write stories about it. For me, being on island in the off-season is so great. It’s when my wife and my boys get to explore for ourselves, hiking snow-covered paths. There are still great restaurants open, too. There’s nothing like going to Via Mare and sitting in front of the fireplace. There’s even a better sense of community than in the summer.”

In the off-season, Greydon House maintains the same standard of service—with friendly, helpful staff. “We make sure that the staff delivers the highest end level of service because we clearly have the highest end product and design,” Beale says. He adds, “We have general contractors walk into Greydon House all year long to see the bathrooms in guest rooms because they had clients stay with us and ask them to replicate what we’ve done. It’s exactly what they want in their house. We know we have a great design. And we know we have a great team that augments that.”

The food at Via Mare is as comforting as the atmosphere. The restaurant is operated by a team that’s well-established across Nantucket. “We’ve been with them since the beginning of 2019, the end of 2018,” Beale says. “They were already established on the island with Ventuno. They took over 21 Federal and established their own beloved Italian restaurant there. The chef and co-owner, Andrea Solimeo, is from Italy. All of his concepts come from Italy. They’re based on his family’s recipes. Their team is really clued into the island. They recently took over The Corner Table, the cafe across the street from Greydon House, too.”

“We love to have people in the off-season,” Beale says. “It’s obviously romantic but it’s a fun time to come visit, too. There are so many little things that people can do. In many ways, you can almost get more value in the off-season because everyone is willing to give you one-on-one attention.” With the ease of access through Tradewind Aviation, the opportunity to explore without summertime congestion and accommodation as pleasing and pleasant as Greydon House, the off-season opens Nantucket to travelers looking for something different than beach days.