Luxury rentals in Nantucket

Find and book unique accommodation on Airbnb

Top-rated luxury holiday rentals in Nantucket

Guests agree: these stays are highly rated for location, cleanliness, and more.

Luxe
Villa in Nantucket
Hilltop Estate
This exceptional collection of homes offers seclusion and serenity in the Nantucket hinterland. Designed by the renowned Lyman Perry, a trio of houses evoke the island’s colonial splendor with sloped porches, stark pillars and radial windows. Grand social rooms, open kitchens and fine bathrooms are bathed in light. Downtown Nantucket, outdoor recreation and tempting food and drink are all nearby. Hilltop estate incorporates a characterful main house, as well as an additional guest house and separate cottage. Extended families or large groups can thus take advantage of ample privacy and space, while exploring the unified themes between each home. The island’s distinct cultural heritage can be traced through the curved, maritime furniture, ceiling decking, prominent pillars and beams, and rustic, shingle exteriors. A unifying theme of white runs throughout, flavored by nautical art and creative flourishes. An especially grand infinity pool is at the property heart, where guests can congregate and appreciate fine weather, while the lengthy dining rooms, bar, and a warming fireplace are ideal for more inclement days.  Nantucket’s gentle, rolling landscape surrounds Hilltop Estate, offering numerous engaging outings and activities. Choose from an impressive range of eateries, seafood restaurants and bakeries, or embrace refreshing walks in the nearby state forest. Take on a dynamic seaside golfing, visit one of the island’s several stimulating museums, or roll out the estate’s complimentary bikes for a relaxed cycle around the locality. With some of the state’s most beautiful beaches within a short drive, Nantucket is your oyster from Hilltop Estate.   Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone bathtub & rain shower, Dual vanity, Walk-in closet, Television, Private balcony • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone shower, Private balcony Sunrise Hideaway Guest House • Bedroom 3: 2 Queen size beds, Shared access to hallway bathroom with bedroom 4, Shower/bathtub combo • Bedroom 4: 2 Twin size beds, Shared access to hallway bathroom with bedroom 3, Shower/bathtub combo Sunset Cottage • Bedroom 5: 2 Twin size beds, Shared access to hallway bathroom with bedroom 6, Shower/bathtub combo • Bedroom 6: 2 Twin size beds, Shared access to hallway bathroom with bedroom 5, Shower/bathtub combo FEATURES & AMENITIES • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below
$6,721 SGD per night
New place to stay
Luxe
Villa in Nantucket
Eastbound
Ideal for a group or family vacation, this is an idyllic, spacious house replete with colonial flavor and set among Nantucket’s historic streets. Boasting a cheery fireplace, chandelier, and ample dining space, fresh Atlantic air flows over the tended, landscaped garden, complete with flower beds and pool. Numerous museums, sandy beaches, quaint streets and tempting eateries are a short walk away. Swaying trees and the dynamic sky of this famous island backdrop the clean, sloped outline of the house, with a pastoral, flagstone path leading to the cheery entrance. Stepping past the shaded porch seats (a favorite afternoon spot), pass through cool air conditioning as you take a seat amongst the pleasantly-lit, fashionable furniture. Tasteful tiling and classic, clear glass runs throughout the home’s numerous bathrooms, while the straight-forward comfort and simple themes of the bedrooms promise a fine night’s sleep. With a full complement of updated appliances, kitchen space and a lengthy dining table, imagine relaxed, laid-back dinners under the soft yellow glow of the overhead chandeliers. Eastbound’s proximity to the core of old Nantucket will add to the sheer convenience of any visit. Guests are just a short walk from quaint parks, stimulating art galleries, and established museums that delve into the island’s rich history, while a bracing swim or sunny afternoon awaits at nearby Steps Beach and Jetties Beach. Get a feel for the island’s geography with eye-opening cliff walks, or hit downtown for a satisfying evening meal, choosing from international choices or renowned seafood.   Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Walk-in closet, Television • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Private balcony • Bedroom 3: King size bed, Ensuite bathroom with with stand-alone shower, Television • Bedroom 4: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Walk-in closet Sunset Cottage • Bedroom 5: Twin size bunk bed, 2 Twin size beds, Ensuite bathroom with shower/bathtub combo FEATURES & AMENITIES • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below
$5,761 SGD per night
New place to stay
Luxe
Villa in Nantucket
Three Cliff Lane
Discover the ultimate Nantucket retreat! Our 5-BR home with a separate 1-BR guest house is the perfect vacation rental in the coveted Cliff area. Relax by the pool in the spacious yard, or take a stroll to Steps Beach just moments away. With a prime location just 1 mile from downtown, you'll have easy access to shopping, dining, and entertainment. This beautifully appointed, Sophie Metz designed property offers the ideal blend of luxury and prime location for your island getaway.
$2,688 SGD per night
5.0 out of 5 average rating, 5 reviews

Popular amenities for Nantucket luxury holiday rentals

Other great luxury holiday rentals in Nantucket

Luxe
Villa in Nantucket
Three Cliff Lane
$2,688 SGD per night
5.0 out of 5 average rating, 5 reviews
Luxe
Villa in Nantucket
Hilltop Estate
$6,721 SGD per night
New place to stay
Luxe
Villa in Nantucket
Eastbound
$5,761 SGD per night
New place to stay
Luxe
Place to stay in Historic district, Nantucket
Morning Dew
$5,376 SGD per night
New place to stay

All about Nantucket

All About Nantucket

The Little Grey Lady Of The Sea

Once the center of America’s whaling industry, Nantucket island transformed into an elite east coast vacation getaway with an average house price of $2.3 million. Colonial buildings and quaint cottages line the main streets of Nantucket Town, while on the outskirts, some of the country’s most impressive mansions populate this nautical paradise. If you love fresh seafood, days on the beach, and evening walks along Main Street; you already love Nantucket.

How to get to the island

Nantucket Memorial Airport, with only 3 runways, shows off its efficiency in the summertime, logging more daily activity than Logan Airport in Boston. If you’re flying in, it’s quickest and easiest to connect through Boston or New York City. If you’d rather bring a vehicle or simply prefer to travel by sea, Hy-line Cruises and the Steamship Authority offer year-round service from Hyannis, MA. And, Freedom Cruise Line and Seastreak provide seasonal high-speed ferries from New Bedford, New York City, New Jersey, and Harwich Port.

Getting around Nantucket

A rich history in whaling

From the late 1700s to the mid 18s, Nantucket’s growing wealth was defined by its whaling industry. Wives of sea captains would spend nerve-wracking evenings staring off into the horizon, hoping to see their husband’s boats coming into port. The town is entrenched in nautical lore, most famously illustrated by Herman Melville in the American classic, Moby Dick. Today, the Nantucket Whaling Museum, a former spermaceti candle factory, shows off the island’s history in observation halls packed with artifacts, photos, and even a 46-foot sperm whale skeleton. The museum is right downtown, so it’s an easy stop before dinner in the Historic District.

Award-winning wine and unbelievably fresh seafood

From the cobblestone streets of the Historic District to the seaside neighborhood around Brant Point, Nantucket is packed with some of New England’s best restaurants. Needless to say, the seafood is the star of the show. The Lobster Bloody Mary at Brant Point Grill is a brunch staple. The raw bar at Cru is famous for its grilled swordfish, lobster rolls, and sweeping views of the megayachts docked in the harbor. If you’re in the mood to discover a new favorite wine with your seafood dinner, Topper’s is well-known for its perfect pairings, with 1,450 wines on hand, and 23 consecutive Wine Spectator Grand Awards under their belt. After dinner, you’ll surely see the locals flocking towards The Juice Bar for milkshakes, waffle cones, and signature smoothies. It’s a good idea to follow.

Golden hour at the Island’s most iconic lighthouse

Established in 1746, the Brant Point Light Station has had its fair share of growing pains. The first 3 light towers burned down, a few were condemned, and one simply blew over, a testament to the power of the Atlantic. But, in 1901, Nantucket got its most popular, postcard-worthy beacon. Today, the Brant Point Lighthouse, a national historic site, stands tall, proud, and bright at the end of Easton Street, about a 10-minute walk from the Whaling Museum.

Classic cars, independent film, and culinary creativity are on display… It’s festival season.

From late April until the end of June, Nantucket is set in festival mode. It all kicks off with the Daffodil Festival. Celebrate spring with an antique car parade, tailgate picnic, and the iconic Nantucket flower show. Next, join world-famous chefs and winemakers for the Food and Wine Festival in May. Then, get your tickets early for screenings at June’s Nantucket Film Festival, showcasing everything from up-and-coming independents to Hollywood blockbusters.

Daytripping from Nantucket to Martha’s Vineyard

Nantucket’s neighbor island, Martha’s Vineyard, is about an hour west on the Oak Bluffs Ferry. Once you step off the boat, it’s just a short walk to the eclectic shops, seafood restaurants, and ice cream bars on Oak Bluff’s busiest one-way, Circuit Avenue. Next, check out the gingerbread cottages in Oak Bluffs Campground, take the kids to Flying Horses Carousel, or stop for a swim at Inkwell Beach. If you’re up for a little adventure, rent some bikes and ride to the border of Edgartown and Oak Bluffs on Beach Road, where you’ll find “Jaws Bridge.” It’s customary for visitors to jump...into the water where they shot Jaws.

Nantucket Beach Guide

North Shore

South Shore

East and West

Nantucket vacation rentals, in and out of town

Staying close to the action, you’ll find most of our Nantucket luxury rentals in the Town and Brant Point neighborhoods. As you move towards the iconic lighthouse, the scenery becomes more about yachts, beaches, and ocean views, while the downtown area is all about short walks to the ice cream shop and quaint cottage lined streets off the main strip. Both neighborhoods are within walking or biking distance of each other, and most of Nantucket’s attractions. If you’d rather a more secluded getaway, keep an eye on the city skyline from the extremely desirable Monomoy area, just off Nantucket Harbour. Calm waters, uninterrupted ocean views, and the island’s best shell fishing make this area quite the catch.

Destinations to explore