It’s been a bust-and-boom year for the summer rental, hotel and lodging business on the Island, after an early wave of mass cancellations shifted quickly to a last-minute flood of demand for bookings. Many rental agents say the shape of the market is different too, with people who are fleeing urban areas after months of quarantine seeking longer stays than in previous years. And more people than ever are coming from neighboring states in New England and New York, filling a gap left by international and long-distance visitors who opted not to come or have been unable to make the trip due to travel concerns and restrictions.

“It has been a complete roller coaster ride,” said Anne Mayhew of Sandpiper Rentals, Inc., which manages rentals for about 700 properties on the Island. “We have seen cancellations, bookings, more cancellations and more bookings.”

But with strict new guidelines for out-of-state travel set to go into effect August 1, hotels and rental agencies believe the ride isn’t over yet.

Hotels and short term rentals around the Island saw demand climb as the summer progressed. — Jeanna Shepard

At the outset of the pandemic in March, Gov. Charlie Baker imposed sweeping restrictions on travel and business, including a ban on all short-term rentals. At first there was quiet anticipation that the economy, and travel, would reopen in time for summer. But when restrictions were extended into June, the cancellations began flooding in.

“The cancellations were fast and furious,” said Julie Flanders, owner of Flanders Up-Island Real Estate. “That was a shock for me. I have been in the business for 40 years and never experienced anything like it before.”

Business at hotels suffered similarly. Fearing devastating economic impact, in early June, 26 hotel and inn owners on the Island sent a letter to Governor Baker seeking guidance from the state to safely reopen their businesses in time to capture what remained of summer. Meanwhile, some homeowners decided to take their rental houses off the market, swallowing the losses and opting to live in the house themselves this summer, booking agents said.

Then on June 8, phase two reopening began in Massachusetts, allowing hotels and short-term rentals to once again host guests after being shut down for almost three months. Rental agencies and hotels said cancellations slowed to a trickle, and then swiftly shifted in the opposite direction, with a run on reservations.

Justin Mercier, general manager of the Mansion House in Vineyard Haven. — Ray Ewing

“It filled right back up,” said Karen Overtoom, owner of Karen M. Overtoom Real Estate and Vacation Rentals, speaking of her 175 rental properties, more than half of which had canceled or had reservations rescheduled for the following year. “Everyone wanted to rebook.”

“We lost so much business in the spring, I would have been happy with any business at all this summer,” said Mark Snider, owner of the Winnetu Oceanside Resort in Edgartown. “Luckily, it has been quite busy since June.”

Though hotels are reporting some vacancies, the scramble continues for last-minute reservations on short-term rentals.

According to Jim Reese of, a wesbite devoted to rentals on the Cape and Islands, bookings have increased 17 per cent on the Vineyard overall this year compared to last year — a sign that the summer rental market is not only recovering despite the pandemic, but thriving because of it.

Many tourists are traveling from neighboring states. — Ray Ewing

Rental agents said the rush of reservations has come with a few unexpected twists. For one, some vacationers are planning to extend their stays longer than the traditional few weeks and stay on the Island until fall. On the high end of the market, rental agents say they are seeing a trend among people seeking to work virtually rather than return to their year-round homes and offices.

“We are doing a lot of last-minute bookings, for anywhere from six to 12 weeks, in the weeks prior to arrival . . . which is very unusual for the Vineyard,” Ms. Mayhew said.

She added: “A lot of our inquiries have said it is really important to have good, functioning internet because they are going to be working from away.”

Rental agents also said vacationers who once were determined to rent in one of the downtown villages are now considering more remote options up-Island. They said some of the most-sought after listings are larger compounds that can house multi-generational families.

Hotel owners and managers said business also began to pick up in early June, with guests staying for longer times, although not as extended as rental homes. Some hotels have adapted to accommodate guests through no contact check-ins. Because the pandemic has made travel plans tentative, some are also allowing guests to cancel with a full refund up to 24 hours in advance.

“We are definitely busy,” said Tania Pereira, general manager of the Summercamp Hotel in Oak Bluffs. “It could be because of coronavirus, but people tend to want to stay longer, enjoy their time a little more.”

George Franz and Bethany Guen enjoy a moment at the Lambert's Cove Inn. — Ray Ewing

Despite the recent boom, rental agents and hotel owners are cautiously awaiting the response to the recent crackdown by Governor Baker on out-of-state travel. Beginning August 1, anyone coming to Massachusetts from outside New England, New York, New Jersey and Hawaii must register with the state and undergo a 14-day quarantine unless they can show proof of a negative test result within the prior 72 hours. Free testing is available on the Vineyard for people who are asymptom

atic, but currently test results are not available for seven days due to extreme national demand for testing.

Ms. Overtoom said 95 per cent of her clients this year hail from neighboring states. Other rental agents cited similar statistics, and said the scant number of people coming from longer distances plan to schedule tests right away.

Booking agents have begun notifying clients of Governor Baker’s order. So far, they said none have canceled.

“It has caused a lot of questions, and we don’t have any answers yet,” Ms. Mayhew said, speaking of the order. “It has been such a journey already . . . we’ll have to wait and see.”