There are two main theories about why Nantucket is nicknamed “The Gray Lady of the Sea.” It might come from the thick fog that often covers the island, which caught the imagination of sailors and whalers arriving at its port as early as the 1600s. Or, it could be because of the cedar-shingled houses, which turn a silvery gray from weathering and salty sea air. It doesn’t really matter which story is true, but this sense of mystery makes visiting Nantucket feel like a special New England getaway. Staying at one of Nantucket’s best Airbnbs makes the experience even better—especially if you’re traveling with a group and need plenty 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 definitely the most popular time to visit Nantucket. Days are spent sunbathing and swimming at the beach, biking to grab a snack from The Green Market, and exploring the Coskata-Coatue Wildlife Refuge. But visiting during other seasons is just as rewarding, especially when activities like stargazing at the Maria Mitchell Observatory are at their best in autumn and winter. (Fun fact: Nantucket is one of the best places to see the Milky Way with the naked eye.)
As for where to stay on your Nantucket trip? Maybe you want a cozy place near town, within walking or biking distance to Cru or the Chicken Box. Or maybe being close to the beach—whether it’s Nobadeer or Madaket—is your top priority. Whatever you prefer, we’ve found the perfect vacation rental for you. Below are the best Nantucket Airbnbs to keep in mind while you plan your summer getaway.
Original Gray Lady
Courtesy of Airbnb
This historic cottage on Hulbert Avenue is in a great spot—across from the beach, a ten-minute walk to town, and with a view of the Great Point Lighthouse from the mahogany deck. The property has been family-owned for over a century and is perfect for multi-generational trips or several couples traveling with kids. Design highlights include Serena & Lily beds, a custom outdoor shower on the deck, and 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
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Chip Chop
Photo: Airbnb
Just a short walk from Main Street and even closer to the beach, this six-bedroom home offers a classic Nantucket escape. As you’d expect from a property this size, it’s well-equipped for large groups: a full chef’s kitchen, a patio with a gas grill, and two sets of LG washers and dryers. If you want to bring your pet, the owners allow up to two well-behaved dogs with prior 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
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Sanford Farm Estate
Courtesy of Airbnb
This large home sits on 1,200 acres of conservation land that stretches all the way to the ocean. Although it feels wonderfully remote, it’s still only two and a half miles from town and right next to the Madaket Bike Path. There’s a heated pool and hot tub (the hot tub is on a bluff with sunset views), and an outdoor shower lets guests enjoy 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 areaHere’s the rewritten version in fluent, natural English:
Beachfront Property with BBQ, Pool, Hot Tub, and Gym
Location: West of Town
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Oceanfront Beach House
Courtesy of Airbnb
“Picturesque” doesn’t quite capture how stunning the views are from this beach house. The Madaket property sits right on the sand, making it easy to stroll over to the shore and enjoy the ocean breeze or check the surf conditions for the day. Back at the house, you can cozy up by the fireplace in cooler months and enjoy outdoor meals all summer long.
Rooms: 3 bedrooms, 3 bathrooms
Amenities: Outdoor shower, washer, AC, indoor fireplace, beach access, BBQ, fire pit
Location: Madaket
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The Beach Plum
Photo: Airbnb
This charming two-bedroom cottage is in the historic Cod Fish neighborhood, just steps from popular spots like Sconset Market and Claudette’s Sandwich Shop. The interiors are bright and lively, matching the bluestone courtyard patio, which features a Kamado grill and a trellised outdoor shower—perfect for summer outdoor living.
Rooms: 2 bedrooms, 2.5 bathrooms
Amenities: Washer/dryer, indoor electric fireplace, beach access, fire pit, BBQ, free parking
Location: Cod Fish Park
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Duck Duck Goose Home
Photo: Courtesy of Airbnb
This renovated historic home was designed by Samuel Masters and has six bedrooms and four full bathrooms—ideal for groups and families. It’s on the edge of the historic district, just a 10-minute walk from town. Enjoy amenities like house bikes and a bluestone patio with a gas grill and teak dining set for outdoor dinners and drinks.
Rooms: 6 bedrooms, 4 bathrooms
Amenities: Washer/dryer, central AC, kitchen, backyard, bikes, BBQ
Location: Downtown
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Sweet Pea Home
Photo: Courtesy of Airbnb
This bright and cheerful renovated home has five bedrooms and three full baths, and is a 15-minute walk from town. (There’s also a nearby walking path and bike path.) Classic Nantucket touches are scattered throughout, like custom cabinetry and a well-chosen collection of antiques, giving the house a warm, lived-in feel.
Rooms: 5 bedrooms, 3 bathrooms
Amenities: Washer/dryer, central AC, heating, kitchen, backyard, BBQ, bikes, outdoor shower, free parking
Location: Downtown
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Mid-Island Home
Photo: Courtesy of Airbnb
This recently renovated home is in the quiet village of Nashaquisset, located mid-island. Guests can use the complimentary bikes to ride into town or to nearby Surfside Beach, or just stay and 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
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Luxury Home with Pool and Water Views
Courtesy of Airbnb
Half a mile from Miacomet Beach, this picture-perfect Nantucket home has a pool, a tall flagpole, manicured green lawns, and waterfront views. It could easily be the setting for a movie scene where a young, impressionable character walks into a chic summer party and warm-weather fun follows. (But that’s just our imagination.)
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
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Three Old Farm
Photo: Courtesy of Airbnb
Maybe it’s a special occasion, or maybe you just want to treat yourself—whatever the reason, if you’re thinking about a big beach vacation, check out Three Old Farm. Its pool is lined with beach roses and has a cabana. There’s outdoor dining for eight and a fire pit perfect 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
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What to Pack for a Nantucket Getaway:
Go for the East Coast prep style with a pair of boat shoes and a classic roll.A neck, and a very fitting cap to protect you from the sun.
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Polo Ralph Lauren
Chino Sport Cap
$55 – SHOPBOP
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L.L.Bean
Boat and Tote Bag
$50 – L.L.BEAN
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J.Crew
2025 Rollneck Sweater
$98 – J.CREW
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Leset
Kyoto Pants
$280 – NET-A-PORTER
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Chimi
Lex Sunglasses
$200 – BLOOMINGDALE’S
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Gianvito Rossi
Vandée Boat Shoes
$845 – NET-A-PORTER
Frequently Asked Questions
Here is a list of FAQs based on the topic 10 best Nantucket Airbnbs for a classic New England getaway
1 What makes an Airbnb a classic New England style on Nantucket
A classic New England Airbnb usually has gray shingle siding white trim cozy fireplaces nautical decor and a big porch with rocking chairs Think lighthouses cobblestones and beachy vibes
2 Is it cheaper to stay in an Airbnb or a hotel on Nantucket
It depends on your group size For couples hotels can be similar in price For families or groups an Airbnb is almost always cheaper because you get multiple bedrooms a kitchen and a living room for one price
3 How far in advance should I book a Nantucket Airbnb
Book as early as possibleideally 6 to 12 months ahead for summer stays Nantucket is tiny and very popular from June to August If you wait until spring most of the best places will be gone
4 Do these Airbnbs come with bikes or beach gear
Many do but not all The articles top 10 often highlights properties that include complimentary bikes beach chairs umbrellas and coolers Always check the Amenities section before booking to confirm
5 Where are these Airbnbs usually located
The best ones are either in Town or Sconset Midisland options are also common but require a bike or car
6 Is it easy to get around Nantucket without a car
Yes especially if you stay in Town Most of the top Airbnbs provide bikes and the island has a reliable shuttle bus If you stay in Sconset a bike is essential but you dont need a rental car
7 What is the biggest mistake people make when booking a Nantucket Airbnb
Booking a place that looks beautiful but is far from everything without realizing you need a car Another common mistake is not checking if the listing has air conditioningmany historic cottages dont and summer can get muggy