2025 Vacation Rental Bookings on the North Shore are behind (And what you can do to increase bookings)
At Wilkuma, we manage vacation rentals across Massachusetts, from Gloucester and South Shore towns like Bourne and Marion, MA. This summer, we’re seeing something unusual: a slower-than-normal start to the short-term rental season.
If you own a vacation rental in this area and you’re wondering why your calendar isn’t filling up yet—or why bookings seem delayed—you’re not alone. Here’s what’s behind the shift and how Wilkuma keeps booking momentum across our portfolio.
The Cold and Rainy Spring has Delayed Demand
Rainy/cold weather from April to June didn’t feel like summer. When the weather doesn’t cooperate, neither does guest behavior. Many travelers pushed off plans until later in the summer or skipped early bookings altogether. This should change as the weather improves.
What we're doing: At Wilkuma, we proactively update listings with flexible check-in windows, local weather perks (like covered porches or indoor games), and real-time photo updates when the sun finally does come out.
Market Saturation + Decreased Early Bookings
In recent years, more homeowners have entered the short-term rental market, and Coastal MA is no exception. But demand hasn’t kept pace, especially not in the shoulder season. That means your listing is competing with more homes for a smaller pool of early-summer travelers. If your vacation rental isn’t being rated as a top rental and your property isn't set up correctly, you’ll have trouble with bookings.
What we're doing: To help with this, we use Pricelabs to adjust rates based on real-time market demand. Lower rates now can mean more 5-star reviews and repeat bookings.
Economic Uncertainty Is Shaking up The Vacation Rental Market
High interest rates, inflation, and general uncertainty have made some travelers cautious. Bookings that would typically occur in April or May are now arriving at the last minute, or not at all.
What we're doing: We keep your listing visible across all major platforms (Airbnb, VRBO, and more), and adjust your rates daily to make sure you're always competitive but we ARE NOT dropping rates to our pricing floor because we are seeing alot of last minute bookings as we progress through the year.
Town Regulations
Some towns on the North Shore and South Shore of Massachusetts have tightened local short-term rental rules, resulting in delays in permitting and increased operational costs. If you're trying to self-manage, it's easy to get caught off guard.
What we're doing: Wilkuma stays on top of local requirements and helps owners remain compliant, so your property isn’t held up waiting for paperwork.
Shift Toward Day Trips, Not Stays
Tourism hasn't disappeared—but how people vacation has shifted. Some travelers are skipping overnight stays and opting for day trips instead, especially when weather or budget constraints are a factor.
What we're doing: We highlight the unique overnight experience your home offers—peace, space, walkability, and that irreplaceable “live like a local” feeling guests can’t get on a quick day trip.
So, What Can You Do as a Vacation Rental Owner?
Don’t panic. A slow June doesn’t mean a bad summer.
Get strategic. If you’re not using dynamic pricing or actively optimizing your listings, you’re falling behind.
Partner with a pro. Wilkuma specializes in Massachusetts vacation rentals. We understand the market, weather patterns, guest expectations, and regulations, and we make your home stand out.
Ready to make the most of your rental—even in a weird season?
Let’s talk. Wilkuma is currently onboarding a limited number of properties in Massachusetts for the 2025 season. Schedule a call to see how we can help you maximize your rental revenue.
