There are two competing theories for Nantucket’s historic nickname, “The Gray Lady of the Sea.” It could be named for the thick fog that blankets the island, which captured the imaginations of sailors and whalers first arriving to its port starting in the 17th century. Or, it could be named for the cedar-shingled houses, which pick up their silvery hue from weathering and the salty sea air. Whichever origin story actually came first doesn’t really matter, but it’s this atmosphere of lore that makes visiting Nantucket feel like a particularly special New England escape. A stay in one of Nantucket’s best Airbnbs cements the experience—especially if you’re traveling with a group, and need a lot of space.

Vogue’s Guide to the Best Nantucket Airbnbs

• For the Best Location in Town: Original Gray Lady, from $2,788 per night
• For a Group or Family Stay: Luxury Home with Pool and Water Views, from $3,293 per night
• For a Sprawling Landscape: Sanford Farm Estate, from $1,459 per night
• For a Home Away From Home: Sweet Pea Home, from $1,234 per night
• For Immediate Beach Access: Oceanfront Beach House, from $2,391 per night
• For Charming Design Accents: Duck Duck Goose Home, from $1,953 per night

Summer is undoubtedly the most popular time of year to visit Nantucket. Days are spent sunbathing and swimming at the beach, pedaling to pick up a snack from The Green Market, and exploring the Coskata-Coatue Wildlife Refuge. But a visit the rest of the year is equally worthwhile, especially when activities like stargazing at the Maria Mitchell Observatory hit their stride in autumn and winter. (Fun fact: Nantucket is one of the best places to view the Milky Way with the naked eye.)

As for where to position yourself for your Nantucket holiday? Perhaps you’re feeling a quaint abode close to town that’s a walk—or a quick bike ride—to Cru or the Chicken Box. Or maybe proximity to the beach, whether its Nobadeer or Madaket, is your priority. Whichever way you lean, we’ve sourced an idyllic vacation rental for it. Below, the best Nantucket Airbnbs to bookmark while you’re busy securing your summer plans.

Original Gray Lady

This historic cottage along Hulbert Avenue is in a prime position—across from the beach, a ten-minute stroll to town, and, in direct view of the Great Point Lighthouse from the mahogany deck. The property has been family owned for over a century and is ideal for multi-generational holidays or several couples traveling with kids. Design highlights include Serena & Lily beds and a custom outdoor shower on the deck, plus gardens designed by The Sconset Gardener.

Rooms: 6 bedrooms, 3.5 bathrooms

Amenities: Bathtub, outdoor shower, washer/dryer, beach access, backyard, fire pit, outdoor furniture, BBQ, EV charger.

Location: Brant Point

Chip Chop

Just a short walk from Main Street and an even closer trot to the beach, this six-bedroom home offers a classic Nantucket escape. As one might expect with a property of this size, amenities are well-suited for large groups: a full chef’s kitchen, a patio equipped with a gas grill, and two sets of LG washers and dryers. And if you’d like to bring your precious pet along for the vacation, the owners permit up to two (well-behaved) dogs with pre-approval and a fee.

Rooms: 6 bedrooms, 3.5 bathrooms

Amenities: Washer/dryer, AC, indoor fireplace, heating, beach access, outdoor furniture, BBQ, free parking.

Location: Downtown

Sanford Farm Estate

This massive home sits on 1,200 acres of conservation land that stretches all the way to the oceanfront. Though the setting feels blissfully remote, it’s still just two and a half miles from town, and conveniently situated right by the Madaket Bike Path. There’s a heated pool and hot tub (the latter is on an elevated bluff, which offers sunset views), and an outdoor shower lets guests soak in the surrounding nature as much as possible.

Rooms: 6 bedrooms, 4.5 bathrooms

Amenities: Bathtub, outdoor shower, washer/dryer, central AC, heating, beach access, backyard, outdoor dining area, BBQ, pool, hot tub, gym.

Location: West of Town

Oceanfront Beach House

“Picturesque” doesn’t quite seem to properly encapsulate just how beautiful the views from this beach house are. The Madaket property is located right on the sand, which makes it all too easy to mosey over to the shoreline to take in the ocean breeze and check out surf conditions for the day. Back at the property, cozy up by the fireplace in the cooler months, and relish al fresco meals throughout the summer.

Rooms: 3 bedrooms, 3 bathrooms

Amenities: Outdoor shower, washer, AC, indoor fireplace, beach access, BBQ, fire pit.

Location: Madaket

The Beach Plum

This charming two-bedroom cottage is located in the historic Cod Fish neighborhood and is steps from favorite spots like the Sconset Market and Claudette’s Sandwich shop. The interiors are bright and energetic, complementing the bluestone courtyard patio (which is fashioned with a Kamado grill and trellised outdoor shower for peak outdoor living in the summer).

Rooms: 2 bedrooms, 2.5 bathrooms

Amenities: Washer/dryer, indoor electric fireplace, beach access, fire pit, BBQ, free parking.

Location: Cod Fish Park

Duck Duck Goose Home

This renovated historic home was designed by Samuel Masters and features six bedrooms with four full bathrooms; ideal for groups and families. It’s located on the edge of the historic district, a mere 10-minute walk from town. Enjoy amenities like house bikes and a bluestone patio complete with a gas grill and teak dining set for al fresco dinner and drinks.

Rooms: 6 bedrooms, 4 bathrooms

Amenities: Washer/dryer, central AC, kitchen, backyard, bikes, BBQ.

Location: Downtown

Sweet Pea Home

This bright and cheery renovated home features five bedrooms and three full baths, and is located a 15-minute walk from town. (There is a nearby walking path to town as well as a bike path.) Quintessential Nantucket touches are peppered throughout the property, such as custom cabinetry and a well-curated collection of antiques, lending the house a gentle, lived-in feel.

Rooms: 5 bedrooms, 3 bathrooms

Amenities: Washer/dryer, central AC, heating, kitchen, backyard, BBQ, bikes, outdoors shower, free parking.

Location: Downtown

Mid-Island Home

This recently renovated home sits in the tranquil village of Nashaquisset, situated mid-island. Guests can hop on the complimentary bicycles to ride into town or to nearby Surfside Beach, or stick around the property to enjoy the neighborhood’s unique charm.

Rooms: 4 bedrooms, 2.5 bathrooms

Amenities: Kitchen, free parking, AC, washer/dryer, backyard, indoor fireplace.

Location: Mid-Island

Luxury Home with Pool and Water Views

A half mile from Miacomet Beach is this picture-perfect Nantucket home. There’s a pool! There’s a sky-high flagpole! There are manicured green lawns and waterfront views! Frankly, it could be setting for a movie scene where our young, impressionable protagonist walks into a chic summer soirée and warm-weather hijinks ensue. (But we’re just projecting here.)

Rooms: 5 bedrooms, 3.5 bathrooms

Amenities: Outdoor shower, washer/dryer, central AC, heating, kitchen, waterfront, backyard, fire pit, BBQ grill, free parking, pool.

Location: Miacomet

Three Old Farm

Perhaps it’s a special occasion, or perhaps you feel like indulging yourself—whatever the reason, if you’re considering a blowout beach vacation, look at Three Old Farm. Its pool is lined with beach roses and has a cabana. There’s al fresco dining for eight and a fire-pit meant for roasting s’mores. Oh, and did we mention the outdoor shower?

Rooms: 6 bedrooms, 6.5 bathrooms

Amenities: Pool, hot tub, kitchen, washer/dryer, central AC, heating, outdoor shower, indoor fireplace, fire pit, BBQ grill, pool house.

Location: Downtown

What to Pack for a Nantucket Getaway:

Lean into the East Coast prep of it all with a pair of boat shoes, a classic rollneck, and a very apropos cap to shield you from the sun.