Seasonal Home Insurance: Preparing Your Martha's Vineyard Property for Time Away
Leaving your Martha's Vineyard home for the winter isn't just about locking the door and heading south. Island life means island risks and when a storm catches you off guard 500 miles away, the consequences can compound fast.
Nor'easters Don't Always Give You Warning
Unlike hurricanes, which can be tracked for a week or more, nor'easters often form within just 100 miles of the coastline and can intensify explosively, sometimes becoming "bomb cyclones" where barometric pressure plummets and winds spike within 24 hours. A quiet forecast on Monday can become a major island-wide event by Wednesday. For a home you're not physically checking on, that speed is exactly what makes off-season damage so dangerous, trees down, roof damage, or a failed heating system can go unnoticed for days.nesdis.
When the Boats Stop, Everything Slows Down
Martha's Vineyard is an island, and that matters enormously during storms. The Steamship Authority routinely cancels or delays trips once sustained wind gusts exceed roughly 30 mph, and cancellations aren't rare, they happened repeatedly this past winter and even during Hurricane Erin's approach in August 2025. When the boats stop running:
Emergency response can slow down. Medevac flights and off-island ambulance transport can be grounded or delayed by the same high winds that cancel ferries, meaning a health emergency at your property could face longer response times than you'd expect on the mainland.
Freight stops moving. Building materials, propane, heating oil, and even everyday groceries largely arrive by boat. A multi-day wind event can leave contractors without materials and grocery shelves thinner than usual, a real complication if repairs are urgently needed after a storm.
Tradespeople get stuck. Many contractors, plumbers, and electricians commute to the island for work. If the boats are cancelled, a repair that seems simple can be delayed for days.
Why a Trusted Caretaker Matters More Than You Think
If you're a seasonal homeowner, a reliable, professional caretaker isn't a luxury it's your first line of defense. Look for someone who will:
Perform a proper seasonal close-down (not just a quick walkthrough)
Physically check the property after major storms, not just periodically
Stay reachable and responsive throughout the entire winter — not disappear for months at a time
Communicate clearly and promptly if something looks wrong
If a dedicated caretaker isn't in the budget, a trusted network of neighbors or friends who can do storm-check visits is the next best option. The point is the same either way: someone needs eyes on your property, especially right after high-wind events.
Heating: A Critical Winter Decision
Frozen and burst pipes are among the most common off-season insurance claims for coastal second homes, and proper planning goes a long way toward reducing that risk. Generally, homeowners choose one of two approaches, and mixing the two is where problems tend to arise:
Option 1: Maintain heat all winter.
Many professionals recommend keeping the thermostat at a minimum threshold, often cited around 50–55°F, to help protect interior pipes from freezing, though the right setting depends on your specific home's insulation, pipe locations, and construction. Talk to a licensed contractor about what's appropriate for your property.
If you rely on mini-splits for heat, ask your HVAC provider about protecting outdoor condenser units from snow accumulation, buried or snow-packed units can stop functioning right when you need them most.
Confirm with your propane or oil provider that they can actually reach your tank throughout the winter. Deliveries typically won't happen if the driveway or path to the tank isn't cleared. Most providers require a clear, unobstructed path (often cited as at least 3 feet wide) and won't push through snowbanks or shovel for you. If a plow contractor buries the tank while clearing your driveway, that's worth catching before it becomes a problem.
Arrange in advance who will clear your specific tank access, not just your driveway, this is a common gap that leads to missed fuel deliveries in the exact week you need heat most.
Option 2: Fully shut the house down for winter.
A full shutdown typically involves shutting off the main water valve and draining the plumbing system, including water heaters, washing machines, and outdoor spigots.
Drain traps and toilet tanks are often treated to prevent freezing and sewer gas issues.
If there's a forced hot water heating system, that too generally needs professional draining or treatment.
Because every property, heating system, and plumbing configuration is different, this decision, and the specific steps involved, should be made with a licensed contractor or plumber who can evaluate your home directly. A partial approach, such as leaving heat on low without confirming tank access, or shutting off plumbing but leaving the thermostat active, is where many preventable claims originate. Whichever route you choose, put the plan in writing with whoever is executing it.
The Bottom Line
Island living means storms can hit hard, help can arrive slower, and small oversights — an unshoveled tank path, an unmonitored mini-split, a caretaker who goes quiet in February — can become expensive fast. A quick call to your agent before the season closes can help confirm you have appropriate coverage in place as you plan for the winter ahead.
This article is provided for general informational purposes only and does not constitute professional, technical, plumbing, or legal advice. Winterization and heating decisions should be made in consultation with a licensed contractor, plumber, or HVAC professional familiar with your specific property. Please contact Sterling Insurance Group to discuss your individual policy and coverage needs.