Cape Cod, Martha's Vineyard and Nantucket Direct Booking Best Practices
You’ve just received a booking request for your vacation rental. The guests are a good fit, the dates work, and they’re ready to move forward. What comes next?
For vacation rental owners—especially those taking direct bookings—one of the most important decisions is how to structure your payment schedule: how much to collect, when to collect it, and how those payments align with your rental agreement and cancellation policy.
There are no single, statewide rules that dictate vacation rental payment schedules. Instead, best practices are shaped by local norms, seasonality, and state law. In highly seasonal markets like Cape Cod, Martha’s Vineyard, and Nantucket, payment schedules tend to be more structured and conservative than in many other vacation destinations.
Below is a practical guide based on long-standing practices in these markets, with notes on Massachusetts law and flexibility for other regions.
The Most Common Payment Schedule on Cape Cod and the Islands
In Cape Cod and Island markets—where prime summer weeks are limited and often booked far in advance—the most common payment structure looks like this:
- 40–50% of the rent due at booking, along with a signed rental agreement
- Remaining balance due 60–90 days before arrival
- All applicable taxes and fees collected with the final payment
- Security deposit or damage protection required before arrival
Today, most owners collect these payments online at the time the rental agreement is electronically signed. This provides immediate confirmation for guests and reduces administrative work for owners.
Because summer weeks are difficult to rebook if canceled late, final payments on Cape Cod, Martha’s Vineyard, and Nantucket are often due earlier than in less seasonal markets. Many owners require full payment for summer rentals by early spring.
An Alternative: Smaller Booking Deposits
Some homeowners choose to collect a smaller initial booking deposit—often a few hundred dollars—to temporarily reserve the dates. The full rental agreement and a larger payment (commonly 40–50%) follow shortly thereafter.
Pros:
- Confirms serious intent early
- Avoids drafting agreements for guests who may back out quickly
Cons:
- Adds an extra step for guests
- Creates multiple payments instead of one clear booking transaction
In Cape and Island markets, this approach is less common today, as most guests expect to confirm a reservation with a signed agreement and a substantial deposit upfront.
Late and Last-Minute Bookings
For bookings made within 60 days of arrival, it is standard practice to require:
- 100% of the rent at booking
- A signed rental agreement at the same time
This is especially important on Cape Cod and the Islands, where a last-minute cancellation during peak season can be very difficult—or impossible—to replace.
Early Bookings for the Following Season
It’s common for guests to book summer rentals many months in advance, sometimes as early as the prior fall.
For early bookings, many owners require:
- 25–50% of the rent at booking
- A signed rental agreement
- A clearly defined balance due date later in the year (often winter or early spring)
Some owners offer split payment schedules, such as:
- One-third at booking
- One-third mid-winter
- Final balance 30–60 days before arrival
This approach can work well when guests are booking far in advance and want flexibility, while still giving owners meaningful financial commitment.
Returning Tenants and Holding Weeks
On Martha’s Vineyard and Nantucket in particular, repeat guests often expect the opportunity to reserve the same week year after year.
A common approach is to:
- Allow returning tenants to hold their week with a small deposit
- Require a signed rental agreement and full deposit by early winter
- Open unclaimed weeks to new guests after a set date
Some owners also offer returning tenants the prior year’s rate as an incentive to commit early. This system rewards loyalty while giving owners clarity before the booking season begins.
Security Deposits in Massachusetts: What Owners Should Know
Short-Term Rentals (Under 100 Days)
Most vacation rentals on Cape Cod, Martha’s Vineyard, and Nantucket are for fewer than 100 days. These short-term stays are not governed by Massachusetts’ residential security deposit law, which gives homeowners flexibility in how security deposits are collected and returned.
Common practices include:
- Refundable security deposits
- Credit card holds
- Non-refundable damage protection policies
Regardless of method, the terms should be clearly spelled out in the rental agreement.
Longer Stays (100+ Days)
For rental arrangements of 100 days or more, Massachusetts security deposit law does apply. In these cases, deposits are capped at one month’s rent and must follow strict handling, accounting, and return requirements.
While long-term stays are uncommon in Cape and Island vacation markets, owners should be aware of the distinction.
Payment Schedules, Cancellations, and Clarity
Your payment schedule should always align with your cancellation policy. Guests should clearly understand:
- When payments are due
- Which payments are refundable
- How cancellation timing affects refunds
Clear, written policies reduce disputes and build trust—especially for direct bookings where guests are not relying on third-party platforms.
Local Rules and Taxes
Massachusetts does not have a single statewide system governing vacation rentals. Instead, local cities and towns may impose registration requirements, safety rules, and occupancy taxes.
Owners on Cape Cod, Martha’s Vineyard, and Nantucket should always confirm local requirements and ensure taxes are collected and remitted properly, either at booking or with the final payment, depending on local rules.
How Payment Schedules Differ in Other Regions
While Cape Cod and the Islands tend to require earlier payments due to seasonality, practices vary elsewhere:
- Year-round or shoulder-season markets may allow balances closer to arrival
- Urban or weekend destinations often require full payment at booking
- International destinations frequently use stricter non-refundable deposits
No matter the location, the most successful owners communicate expectations clearly and collect payments in a way that protects both parties.
Final Thoughts
There is no one-size-fits-all payment schedule for vacation rentals—but in high-demand, short-season markets like Cape Cod, Martha’s Vineyard, and Nantucket, clear and structured payment timelines are essential.
By setting expectations upfront, aligning payments with cancellation policies, and using reliable booking management tools, owners can reduce risk, avoid confusion, and create a smoother experience for guests.