Second Home Insurance in Connecticut

By Jon Merwin, Founder and CEO, Licensed Insurance Advisor

Connecticut has two kinds of second-home country. Along the eastern shoreline, families keep summer places in Old Lyme, Old Saybrook, Madison, Guilford and Stonington. Inland, the Litchfield Hills draw weekend owners to Salisbury, Washington, Roxbury and Sharon, and the lakes, from Candlewood to Waramaug and Bantam, fill with seasonal houses. Many of the owners live in New York or elsewhere in New England and visit a few weekends a month. Insuring a house that sits empty most of the week takes different questions than insuring the place you live.

Portsmouth Atlantic Insurance is an independent agency, family-owned since 2005, that shops 40+ carriers. We serve Connecticut from our Connecticut office and by phone, email and online. Phone (603) 431-4020 or email insure@portsmouthatlanticins.com.

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Where Connecticut second homes cluster

The Census Bureau’s 2020-2024 American Community Survey counts more than 1,200 homes held for seasonal, recreational or occasional use in each of Old Saybrook and Old Lyme, and several hundred each in Madison, Salisbury, Guilford, Stonington and New Fairfield. These are also some of the state’s more affluent towns: median income in Madison, Old Lyme, Lyme and Guilford runs well above the state figure, and the median home value in Salisbury, Roxbury and Washington is roughly twice the Connecticut median.

• Eastern shoreline: our Madison, Guilford and Lyme pages, plus coastal home insurance in Connecticut: flood, wind and storm deductibles.
• Litchfield Hills: Litchfield Hills high-value home insurance, Roxbury and Bridgewater and Goshen.
• Candlewood Lake: Sherman high-value homes and New Fairfield.

Unoccupied or vacant: the distinction that matters most

Second-home claims often turn on whether the house was occupied. A report from the legislature’s Office of Legislative Research sets out the usage insurers follow: an unoccupied dwelling has furniture and personal belongings and is visited periodically, while a vacant one has been emptied. The report notes that policies commonly restrict vandalism, water and burst-pipe claims after a stretch of vacancy, and that insurers treat unoccupied homes case by case, especially when they have been told about the situation and the owner keeps the heat on, has an alarm and has someone check the house.

The Connecticut Insurance Department’s homeowners FAQ lists physical changes that make a property uninsurable among the reasons a policy can be canceled, giving a home vacant for more than 60 consecutive days as its example. The state’s FAIR Plan, the insurer of last resort, says in its producer manual that a dwelling vacant or unoccupied for 60 or more consecutive days does not meet its underwriting standards. Our post on whether homeowners insurance covers a vacant property goes into more detail.

What this means in practice:

• Keep the house furnished and visited. Log visits by you, a caretaker or a property manager, especially after storms and cold snaps.
• Tell us before a long gap, a sale or a major renovation. Carriers have endorsements and policy types for each, and telling them first is what keeps a claim from becoming a dispute.
• Keep the heat on through the winter, and install a low-temperature alert and an automatic water shutoff valve. Many carriers ask about both on a seasonal home.

Shoreline second homes: flood, hurricane deductibles and disclosure

Long Island Sound houses face two storm questions. The first is the hurricane deductible. Connecticut lets an insurer use one only for damage during a window that opens with a National Hurricane Center hurricane warning for any part of the state and only if the storm brought hurricane-force sustained winds to some part of Connecticut. Our guide to hurricane deductibles in Connecticut walks through the trigger and how to find the dollar amount on your declarations page.

The second is flood, which no homeowners or dwelling policy covers. Public Act 25-33 added six flood questions to the seller’s property condition report starting July 1, 2025, and since July 1, 2026, lenders and insurers must give written notice that homeowners insurance does not cover flood. If you are buying a cottage on the water, read the flood answers before you sign; our post on the Connecticut flood disclosure law explains each one. For Connecticut flood coverage, we offer NFIP policies through Selective and private flood through Flow Flood, Neptune Flood, Beyond Floods, The Flood Insurance Agency, CatCoverage and Aon Edge. See our flood insurance page.

Hills and lakes: winter, wells and water

• Burst pipes. A Litchfield County house left at a low thermostat setting over a January week is the classic second-home claim. Insulate exposed pipes, have someone check after an outage, and consider a whole-house shutoff that closes when it senses a leak.
• Wells and pumps. Most hill-town houses run on private wells and septic. Equipment breakdown and service line endorsements pick up some failures that a base policy leaves out, though wear and tear is never covered.
• Wood stoves and fireplaces. Tell the carrier about every wood or pellet stove, keep it cleaned and inspected, and let guests know the rules.
• Long driveways and response times. A house at the end of a dirt road far from a fire station is underwritten differently than a village home. Monitored smoke and heat alarms help.
• Docks and boats. A dock, a boathouse or a boat on Candlewood or the Connecticut River needs attention on both the home and boat policies; see boat insurance in Connecticut.

Renting the house when you are not there

Renting a Connecticut second home changes both the taxes and the insurance. The Department of Revenue Services’ special notice on short-term rentals explains that since October 1, 2019, short-term rental platforms that meet the state’s threshold must collect and remit room occupancy tax on the Connecticut stays they book. An owner who rents only through such platforms is not liable for collecting the tax on those stays, but an owner who also books guests directly is the retailer for those stays and must register and file through the room occupancy tax process.

On the insurance side, a homeowners policy for a secondary residence is not designed for paying guests. A few weeks a year may be handled with an endorsement; a house rented for most of the summer season is better on a policy built for vacation rentals, such as Proper Insurance. Year-round tenants move to a landlord policy; see landlord insurance in Connecticut. Some shoreline and lake towns regulate short-term rentals by zoning, so check with the town before you list.

Liability for a house you are not always at

Guests, contractors, caretakers and neighbors’ children on the dock are all part of second-home liability. The liability on the second home policy should match the limits on your primary home, and your umbrella carrier needs to know the second home exists so the umbrella sits above both. Our umbrella insurance in Connecticut page explains how that works. Owners who hold the house in an LLC or a trust should make sure the named insured on each policy matches the deed.

Carriers for Connecticut second homes

Our Connecticut home carriers include Vermont Mutual, Andover, Providence Mutual, Liberty Mutual, Foremost, Openly, Stillwater, Cincinnati, National General and Hanover, and Chubb writes in every state where we are licensed. Each sets its own rules for secondary and seasonal homes, so we ask which will write the house and on what form. Cincinnati and Chubb both write homes at any dwelling limit, so we quote both on larger houses; our Connecticut high-value home insurance page covers that market. For a primary residence, start with homeowners insurance in Connecticut.

Get a quote on your Connecticut second home

Tell us where the house is, how it is used and who looks after it. We compare carriers for the right fit, and we don’t charge any fees. If a storm or a burst pipe leads to a claim, we stay involved until it is paid. Request a quote. There’s no obligation to buy. Start with the form below or our quotes page, or call (603) 431-4020. The office is open 9 to 5 Monday to Thursday and 8 to 4 on Friday, Eastern time. Other owners share their experience on our client feedback page.

Frequently asked questions

Can my Connecticut second home go on my primary homeowners policy?

Usually not on the same policy. Carriers write a second home as a secondary or seasonal residence, often on its own homeowners or dwelling policy, because nobody is there most of the week and the risks are different. Your liability coverage and umbrella should still be coordinated across both homes, which is easier when one agent handles them.

What is the difference between a vacant and an unoccupied house?

A report from Connecticut’s Office of Legislative Research explains the industry usage: an unoccupied house has furniture and belongings and is visited periodically, while a vacant house has been emptied of contents. A furnished weekend house is normally unoccupied, not vacant. Vacancy is what triggers restrictions, and the Insurance Department lists a home vacant for more than 60 consecutive days as a reason a carrier may cancel.

Does Connecticut require flood insurance on a shoreline second home?

State law does not require it, but a lender will if the home is in a FEMA special flood hazard area and carries a federally backed mortgage. Since July 1, 2025, Connecticut sellers also answer six flood questions on the property condition report, so a buyer can see past flood claims before closing. A homeowners or dwelling policy never covers flood; that takes a separate NFIP or private flood policy.

When does a hurricane deductible apply in Connecticut?

Only during a window tied to a National Hurricane Center hurricane warning for part of Connecticut, and only if the storm produced hurricane-force sustained winds somewhere in the state. Otherwise the regular deductible applies. The deductible is figured on the dwelling limit, not the size of the loss, so check the dollar figure on your declarations page.

Do I need to collect room occupancy tax if I rent my Connecticut house?

If you rent only through a platform that collects the tax for you, the Department of Revenue Services says you are not liable for collecting it on those bookings. If you take any bookings directly, you are treated as the retailer for those stays and need to register, collect and file. Check with a tax adviser for your situation, and tell us about any rentals so the insurance matches.

Which carriers do you use for Connecticut second homes?

We start with our Connecticut home carriers, including Vermont Mutual, Andover, Providence Mutual, Liberty Mutual, Foremost, Openly, Stillwater, Cincinnati, National General, Hanover and Chubb, and ask which will write the house as a secondary residence. Cincinnati and Chubb both write homes at any dwelling limit, so we quote both on larger houses. Proper Insurance handles homes rented short term.

What do you need to quote a Connecticut second home?

The address, how many weeks a year someone is there, who checks on it when you are away, the heating system, whether it has a well, a wood stove, a dock or a pool, and whether you rent it. Your current declarations page helps. Request a quote. There’s no obligation to buy. Reach us at insure@portsmouthatlanticins.com, through the form on this page, or at (603) 431-4020.

Sources

• U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates, tables B25004, B19013 and B25077 (via Census Reporter)
• Connecticut Office of Legislative Research, Insurance on Vacant Property (2001-R-0731)
• Connecticut Insurance Department, Homeowners Insurance FAQs
• Connecticut FAIR Plan, Producer Manual (rev. June 2025)
• Connecticut Department of Revenue Services, SN 2019(9), Room Occupancy Tax on Short-Term Rentals
• Connecticut Department of Revenue Services, Room Occupancy Tax Information

This guide is general information for Connecticut second-home owners and is not legal or tax advice. Policy wording, endorsements and each carrier’s underwriting decide what is covered. Tax rules and town ordinances change, so confirm current requirements with the Department of Revenue Services and your town. To review your own house, call (603) 431-4020.