Hilltop Estate

Entire villa in Nantucket, Massachusetts, United States

10 guests
6 bedrooms
10 beds
5.5 bathrooms

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Extraordinary homes, vetted for quality.

Hosted by Lois

6 years hosting

Listing highlights

Now accepting reservations

Be the first to discover this home.

Breathtaking views and the prettiest pool on the island. Just bring your swimsuit- we provide everything else! Rent for 31 days and avoid the Nantucket tourism tax.

A sprawling "post & beam" property, impeccably maintained & professionally decorated. The home is surrounded by landscaped grounds and features abundant outdoor living spaces. With three buildings, the house is perfect for your extended family.

Please contact me directly about 2026.

The space
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.

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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

Registration details
029616