Guide

What to ask a Martha's Vineyard caretaker before you hire one

Last reviewed October 20, 2026

For much of the year, a caretaker may be the only person who sees your house on Martha's Vineyard. This guide covers what caretakers do, the questions to ask before you hire one, and what to check in your own insurance policy, with a short checklist at the end.

What a caretaker does

A caretaker looks after a house while the owner is away. The usual work is a house check on a set schedule, storm preparation and a walk-through afterward, opening and closing the house at each end of the season, letting in the trades and deliveries you have booked, and getting the house ready before you arrive.

Plumbing, gas, electrical and alarm work is for licensed trades, covered below. A caretaker checks the house on a schedule and does not patrol the property or respond to alarms. A property manager usually does more, such as hiring and paying contractors and keeping a budget for the house. A rental manager finds guests, takes bookings and collects rent. MV Caretaking does not handle rentals of any kind, so if you rent the house out you will need a separate arrangement for that.

Insurance: what to ask for

Start with general liability. A commercial general liability policy covers the business's legal liability for injury or damage to others arising from its operations [1]. Ask whether the caretaker carries it, with which company, and at what limits.

Then ask about your things while they are in the caretaker's hands. The standard general liability form excludes damage to personal property in the care, custody or control of the insured, and whether it applies to a given loss depends on the facts [2]. Think of the outdoor furniture carried into the garage before a storm. Ask the caretaker's agent what the policy would pay if something of yours were damaged while the caretaker was responsible for it, and get the answer in writing.

Ask about workers' compensation if the caretaker has employees or brings helpers. Every employer in Massachusetts must carry it for its employees, whatever the number of employees or hours worked, while sole proprietors and LLC members are not required to cover themselves [3]. A caretaker who works alone may lawfully have no such policy, but one who sends a crew should. General liability does not cover it [1]. Ask your own insurer how your homeowners policy would treat an injury to someone working at the house.

For proof, ask the caretaker's agent to send you a certificate of insurance. Check the names, policy types, limits and dates, and ask for a new one each year. Under Massachusetts law, a certificate is not a policy, does not change the coverage in the policy it describes, and gives you no rights beyond what that policy expressly provides [4]. If a particular risk matters to you, ask the agent whether the policy covers it.

References from other owners

For contractors, the state suggests asking for written references for the three most recent jobs, with the homeowners' names and phone numbers, and then calling them [5]. Do the same with a caretaker, choosing owners whose houses they have looked after through at least one winter, ideally in your town. Ask each one whether a report came after every visit, what happened after the last big storm, and whether the bills matched what was agreed.

House checks and reports

Ask how often the caretaker will check the house in each season and what a check includes. A useful check notes that the heat is running and the indoor temperature, looks for water on floors and ceilings and for a damp smell, tries doors and windows, and walks the outside after wind. Ask for a dated note with photos after each visit, agree on how it reaches you, and keep the reports. If something goes wrong later, they show when the house was last seen and in what condition.

Your own policy: vacancy and freeze conditions

Your homeowners policy has its own conditions for an empty house. Massachusetts law sets out a standard fire policy under which, unless the policy says otherwise in writing, the insurer is not liable for a loss while a residential building of three units or less has been vacant or unoccupied for more than sixty consecutive days [6]. A sample standard homeowners form published by the Insurance Information Institute drops cover for vandalism and glass breakage once the dwelling has been vacant for more than 60 consecutive days. It also excludes freeze damage to plumbing, heating and air conditioning systems unless you used reasonable care to maintain heat, or to shut off the water and drain all systems and appliances [7]. The Massachusetts Division of Insurance warns that most homeowners insurance covers sudden and accidental water damage from a burst pipe only if the home was properly heated and not left unoccupied [8].

Your policy may be worded differently, so read it. Ask your agent what it requires while the house is empty: a minimum temperature, a water shut-off, how often someone must check the house, and whether you need an endorsement. Get the answers in writing and give a copy to your caretaker, so the check schedule matches the policy.

Storms and winter response

Ask how soon the caretaker can reach the house after a storm and how many other houses they look after. In the February 2026 blizzard, all boats to and from the island were canceled on the day of the storm, and the governor's office issued a travel ban for Dukes County that evening [9]. A caretaker who lives on the island can get to the house once the roads are safe. One who comes over from the mainland may have to wait for the boats. Agree on when they call you before calling a plumber or electrician, and how much they may spend in an emergency without asking.

Keys, codes and access

Ask who will hold your keys and how they are stored. A key tag should not carry your address. Ask where alarm and lockbox codes are kept and whether anyone besides the caretaker can reach them. Agree on what happens to keys and codes if you stop working together, and change the codes when that happens.

Which work goes to licensed trades

Ask which jobs the caretaker does and which go to a licensed trade. In Massachusetts, only a licensed master or journeyman plumber, with a permit from the local plumbing inspector, can do plumbing work in your home, and the same state board licenses gas fitters and propane installers [10]. Electrical work needs a licensed electrician, and only licensed systems contractors or technicians can install or repair security or fire alarm systems [11]. Both boards let you check a license [10] [11]. If the caretaker books trades for you, ask whether they add a fee and whether you will see the trade's own invoice.

Contractors working on an existing, owner-occupied home of one to four units must register as home improvement contractors, and structural work generally needs a construction supervisor license. That registration law does not cover vacation or secondary homes [5], so for a seasonal house its arbitration program and guaranty fund may not be open to you. A clear written agreement matters more for that reason.

The agreement and the bill

The state's advice for plumbing and electrical work is to agree in writing on scope and price [10] [11], and the same holds for a caretaker. The agreement should list the services, how often visits happen, what a visit includes, how reports reach you, and the price per visit or per month. It should say what is billed extra, such as storm visits, trips to let trades in, waiting time and supplies, and how either side can end it. Prices vary, and each caretaker sets their own.

When they are off-island or sick

Ask who covers the house when the caretaker is away or ill. Get the backup's name and number, find out whether the backup has keys, and ask whether you will be told when someone else is covering.

Checklist for the first conversation

• Certificate of insurance from the caretaker's agent, with general liability limits and dates [4].
• A written answer on damage to your property while it is in the caretaker's care [2].
• Workers' compensation if they have employees or bring helpers [3].
• Three references from owners they have served through a winter [5].
• How often they check in each season, and what a check covers.
• A dated report with photos after every visit.
• How soon they can reach the house after a storm.
• Who holds keys and codes, how they are stored, and what happens to them if you part ways.
• Which work goes to licensed plumbers, gas fitters, electricians and alarm contractors [10] [11].
• A written agreement with prices, extra charges, an emergency spending limit and notice terms.
• A named backup for when they are away.
• Your own insurer's requirements for an empty house, in writing [6] [8].

Sources

1. Insurance Information Institute, Commercial general liability insurance.
2. Craig Stanovich, Care, Custody, or Control Exclusion in the CGL, IRMI, October 1, 2008.
3. Massachusetts Department of Industrial Accidents, Workers' Compensation Insurance Requirements.
4. Massachusetts General Laws, Chapter 175L, Section 2 (certificates of insurance).
5. Massachusetts Office of Consumer Affairs and Business Regulation, HIC Homeowner Resources.
6. Massachusetts General Laws, Chapter 175, Section 99 (standard fire insurance policy).
7. Insurance Services Office, Homeowners 3, Special Form (HO 00 03 10 00), sample policy, published by the Insurance Information Institute.
8. Massachusetts Division of Insurance, Massachusetts Cold Snap: Don't Let Frozen Pipes Become Your Next Insurance Claim, January 21, 2026.
9. Hayley Duffy, Blizzard buries Island, The Martha's Vineyard Times, February 26, 2026.
10. Massachusetts Board of State Examiners of Plumbers and Gas Fitters, Plumbers and gas fitters consumer fact sheet.
11. Massachusetts Board of State Examiners of Electricians, Electricians consumer fact sheet.