These Branded Nantucket Homes Give You All the Perks of Hotel Life

Last spring, an affluent Manhattan-based family was conducting their annual search for an August rental in Nantucket. They found many contenders for their multigenerational vacation, but each house fell through for different reasons: One was too far from town, another did not allow children under the age of 12. Real-estate agents told the family that most of the prime and sought-after homes had been rented months ago. 

Alas, they were too late. But in late July, a new option came across the transom: three-bedrooms with a yard in the tony Brandt Point area. It checked all their boxes. The family signed a lease. A few days later, however, they learned that the rental had fallen through because the current tenants decided to extend their stay on the island. 

They were back to square one. 

“We felt completely left in the lurch,” said one of the family members, who asked to remain anonymous. At that point in the summer, the rental inventory scarce, so they started looking into hotels, but the economics of individual rooms didn’t make sense. Plus, they all wanted to be together under one roof. But they made a surprising discovery: Some of the properties they were looking at, such as Greydon House, the Wauwinet, and the White Elephant, rented stand-alone residences suitable for families. 

And they came with other perks. For one thing, they didn’t have to pay the 11.7 percent rental tax. Many of these branded homes also came with hotel amenities, such as housekeeping and concierge services at a similar price point, and in some cases, even less than many of the traditional rentals they had been considering. The family ultimately decided to stay five nights at the Greydon House–owned 52 Union, a $2,500-a-night, three-bedroom house in the downtown area with views of the harbor, followed by a weekend at the Wauwinet’s three-bedroom Serena & Lily–decorated Anchorage House. 

“It’s getting to the point where people are starting to book fairly early. Everyone wants the peak weeks in July and August, and we don’t have a ton of availability. I always urge people to lease at least by March,” Bobby Sabelhaus, an agent with Great Point Properties in Nantucket, says. “Nantucket has never been this popular.” The relator has been visiting the island since the 1980s and currently lives there year-round. At Great Point Properties, one of the largest Nantucket real-estate companies, lease activity increased around 1.3 percent from 2023 to 2024, with the average rent of around $13,000 a week. (The average lease term was 12 days.) 

Another factor in the cutthroat Nantucket rental market is the community divide over short-term leases—which broadly boils down to the tension between overcrowding and traffic and being a hospitality town that depends on tourism. The issue of short-term rentals continues to be battled out in town hall meetings and courts. 

Earlier this year, the Copley Group, one of the largest operators of short-term rentals in Nantucket, put close to $40 million of its real-estate portfolio on the market because of a ban on corporate ownership of short-term rentals. Regulations aside, which if enacted and enforced could certainly further squeeze the already ultra-competitive Nantucket rental market, is that hospitality companies, with their full fleet of amenities and services, could push local landlords to up their offerings. 

Nantucket, which has been called a place where billionaires go to escape millionaires, is probably one of the only places in the world where even if you are spending $200,000 a month to rent a $20 million home, you will still be asked to start the dishwasher, strip the sheets, start a load of towels, and sort of the recycling in advance of the cleaning crew’s arrival. (Non-compliance can result in the substantial dinging of your security deposit, which is typically 10 percent of the total rental amount.) 

“We don’t get a lot of push back on these things,” Sabelhaus says. “People will follow instructions, whether it’s a $5,000 or a $50,000 rental.”

Still, hospitality brands are coming in to fill these service gaps, among other parts of the often-rigid Nantucket rental market. Greydon House, which has four standalone guest houses in its portfolio ranging from a bungalow ($2,500 per night) to a five-bedroom house in Madaket with an in-ground pool ($3,000 per night), has the flexibility to offer three-night minimum stays.

“Allowing our customers to come for less than seven days has helped our houses’ popularity and demand,” says Evan Leventhal, revenue manager of Greydon Hotel Group. (During the high season, Greydon’s House occupancy is 80 to 85 percent.) The hotel group’s foray into the home rental market started in 2018 when Greydon House turned a 1,600-square-foot apartment, now called the Bungalow, into a three bedroom and three-bathroom duplex. “The Bungalow was in such high demand, we decided to buy our second house—52 Union—and make it a more upscale version of the Bungalow. Our goal is to make sure our houses are still walkable to town yet retain the quality and services of a high-end boutique hotel,” Leventhal explains. 

For Greydon House, that means offering exclusive experiences to guests, such as booking sailing trips on the Blue Peter, a 65-foot teak 1930s sailing yacht, tours of the Maria Mitchell Association/Loines Observatory, concierges who will book treatments and massages through Lavender Farms Wellness, and private access to the Harvest Garden, an organic farm and event space. (Great Point Properties refers renters to third-party concierges such as Help Me Rhonda, but they don’t book those services directly.)

What many of these hoteliers are tapping is the high-touch, five-star service this younger, well-heeled generation of travelers expects at this price point. 

“The idea of renting a house sounds great until you arrive and realize all the housework and cooking you have to do at home follows you on vacation,” says Jason Brown, CEO of Blue Flag Capital, which recently opened the Beachside hotel in Nantucket. “From our pre-arrival concierge to assist with all your activities and reservations to on-sight F&B and housekeeping, when you stay in the family suites at Beachside or the Federal Suite at Faraway, you are getting the best of both worlds.”

These newer hotel-branded residences are conceived with families in mind. The Manhattan family says they had to pass up at least three rentals because they were not suitable for young children, in one case because of a steep staircase and in the others because of proximity to busy roads.

At Beachside, located walking distance from downtown, there are family suites, starting at $1,299 per night, that can be configured for anything from two bedrooms to five bedrooms. They also have a kids’ club, a guest-only pool, and multiple on-site dining options. The Federal Suite ($3,500 per night), also in a prime location near town, has a kitchen, two patios, and three bedrooms. 

While the Wauwinet hotel is adults-only, the stand-alone cottages, which range from one to three-bedrooms, allow children. At the island’s only Relais & Chateaux property, guests staying in the Wauwinet’s cottages have access to BMW test-drives, tennis courts, a harbor and Atlantic beach, culinary and mixology classes, and guided tours to local destinations. Occupancy from May to September averages above 90 percent for the cottages, where nightly rates range from $3,900 to $7,500 during peak season. 

While that easily totals a jaw-dropping $50,000 tab for a week in Nantucket, a comparable rental with all those amenities would cost as much if not more because of the additional 11.7 percent rental tax and 10 percent security deposit. And it’s extremely rare to find a rental house a stone’s throw from two beaches with a tennis court and that offers twice daily housekeeping as part of the rental price.   

Another hospitality company with a presence on Nantucket, which asked not to be identified because of the unresolved issues over short-term rentals, frames their pitch as: “Don’t separate trash or start laundry.” This luxury group advertises “hassle-free stays” made possible by an on-site concierge team to manage every detail. “Need groceries? They’ll get them. A night out? They’ll book it. Want a massage? A yoga instructor? A private chef? Just ask.”