The 14 day rental rule in the Hamptons is real, and it works. If you use a dwelling unit as a residence and rent it for fewer than 15 days, you don’t report any of the rental income and you don’t deduct any expenses as rental expenses. Two summer weeks of Amagansett rent, off your federal return.

Here’s what nobody tells you across the desk until it’s too late. That federal break does nothing about the Suffolk County occupancy tax, nothing about New York sales tax, and nothing about whether your town will even let you rent for two weeks in the first place. In Bridgehampton, it mostly can’t be done at all.

October is the right month to work this out. Summer 2027 bookings get talked about now, and the permits, registry numbers, and tax registrations all have to be in place before a guest shows up.

What the federal 14-day rule says

Two conditions, both required.

First, you have to use the place as a residence. You’re considered to use a dwelling unit as a residence if you use it for personal purposes during the tax year for more than the greater of 14 days, or 10% of the total days you rent it at a fair rental price. So if you rent 14 nights, 10% is 1.4 days, and the test lands on 14. You need at least 15 personal-use nights in that same calendar year.

Second, the house has to be rented for fewer than 15 days. Fourteen nights is the ceiling, not the target.

Miss the first test and the rule doesn’t apply at all. We see this with owners who bought recently, spent a long weekend out east, and rented the house for two weeks in July. Ten personal nights and fourteen rental nights is not a 280A(g) situation. That’s a taxable rental with prorated expenses.

One more piece worth knowing: mortgage interest, property taxes, and any qualified casualty loss are still reported as normally allowed on Schedule A. You lose the rental deductions, not the itemized ones.

Local rental rules by town and village

This is where East End owners get tripped up, because the same number 14 shows up in local codes pointing the other direction.

Amagansett and the rest of unincorporated East Hampton Town

Under the Town Code, a property owner can rent a residential property up to twice in six months if the rental period is less than two weeks. Rentals of two weeks or longer have no limit.

Owners who rent by the week, month, season, or year must register with the Town and obtain a Rental Registry Number. The registry number has to appear in rental ads, and the Town checks for it.

Bridgehampton and the rest of unincorporated Southampton Town

The minimum length of stay under the Southampton Town Code is currently 14 days. Anything shorter is a transient rental and isn’t allowed. There is no maximum stay. The code itself defines “transient” as a rental period of 14 days or less, and a rental permit is required for any home rented for any period of time.

Read those two together and you’ll see the problem. The code bans 14 days or less, while the Town’s own FAQ says the minimum is 14 days. Either way, a two-week whole-house rental in Bridgehampton sits right on a line the Town enforces, and a 15-night stay to be safe puts you over the federal limit. Call the Town before you plan around it.

Sag Harbor Village

Village Code Chapter 215 defines a short-term rental as a rental period of 14 days or less, added by Local Law No. 8 of 2024. No one may collect rent without a valid rental permit, and no rental permit is granted for a non-owner-occupied short-term rental. So for a village house you don’t live in, the federal 14-day play isn’t on the table.

The village also straddles both East Hampton Town and Southampton Town, so confirm which set of rules covers your address before you book. See our Sag Harbor service area page for more on the local rules.

Taxes that still apply: county occupancy tax and sales tax

Every facility providing short-term lodging of less than 30 days for a fee in Suffolk County must collect occupancy tax at 5.5% of the per diem rental rate, effective June 1, 2023. The law applies to all lodging facilities, including residences and tourist homes. There’s no 14-day carve-out. The only way out is the 30-day permanent resident rule.

Lodging facilities must register with the County within ten days of their first rental. Returns and payments are quarterly.

Then there’s sales tax. For rent collected by an operator or booking service on and after March 1, 2025, New York State and local sales tax applies to short-term rental unit occupancy. Suffolk County raised its local rate from 4¼% to 4⅜% on the same date, which puts the combined rate at 8.75%.

So your “tax-free” two weeks still carries roughly 14.25% of tax on top of the rent.

Amagansett example: 14 nights rented vs. 15 nights rented

Made-up inputs, real rates. Say an Amagansett owner lists at $1,800 a night for summer 2027 and uses the house themselves for 21 nights.

Item	Plan A: 14 nights rented	Plan B: 15 nights rented
Gross rent	$25,200	$27,000
Reported on Schedule E	$0	$27,000
Allocable expenses (15/36 of $40,000)	None deductible	$16,667
Net rental income	$0	$10,333
Federal tax at a 24% example rate	$0	$2,480
Kept after federal tax	$25,200	$24,520

The 15th night brought in $1,800 and cost about $2,480 in federal tax, before New York State income tax. You netted roughly $680 less for doing more work.

The $40,000 here stands for utilities, insurance, cleaning, landscaping, repairs, and depreciation, not mortgage interest and property taxes, which follow their own allocation rules. If your allocable expenses are high enough to swallow most of the rent, the extra night is closer to a wash. Run your own numbers before you decide.

On top of either plan, the guest pays more. On $25,200 of rent, the 5.5% county occupancy tax is $1,386 and 8.75% sales tax is $2,205, so the guest writes a check for $28,791. The county tax is computed on the per diem rate without sales tax included. Whether the occupancy tax belongs in the sales tax base is a detail worth confirming with your preparer.

When the 14-day rule doesn’t fit

Skip the 14-day plan if the house is a pure investment property you never stay in. No residence, no exclusion, and you’re better off running it as a real rental with full deductions.

Skip it if you’d have to shave a booking down to make it fit and the house is in Southampton Town, where short stays are the problem rather than the solution.

Skip it if you’re already renting the whole season. Rentals of 30 or more consecutive days make the occupant a permanent resident, exempt from the 5.5% tax, and the income is taxable either way. A June-through-August tenant is usually the simpler business.

And don’t let the tax tail wag the dog. Fourteen nights of rent on a house you love, with strangers in it twice, is a lifestyle decision first.

Frequently asked questions

Does the 14-day rule mean my Hamptons rental income is completely tax free?

No. It’s free of federal income tax, and because New York starts from your federal adjusted gross income, it generally stays off the state return too. The 5.5% Suffolk occupancy tax and 8.75% sales tax still apply to any stay under 30 days.

Can I do a 14-day rental in Bridgehampton?

Probably not as you’re picturing it. Southampton Town treats anything shorter than a 14-day rental as a transient rental that isn’t allowed under the Code, and the code’s own definition of transient reaches 14 days. Confirm with Town code enforcement before you book.

How many nights can I rent in Amagansett and still qualify?

Two one-week stays work. That’s 14 rental nights, which fits the federal ceiling, and two short rentals, which fits East Hampton Town’s limit of twice in six months for rentals under two weeks. You’ll need a registry number first.

Who collects the occupancy tax if I book through Airbnb?

Suffolk County approved a voluntary collection agreement with Airbnb in June 2025, under which Airbnb remits the lodging taxes. If you rent privately or through a broker, that’s on you, and registration is due within ten days of your first rental.

Will I get a 1099-K for two weeks of rent?

For 2026 the federal threshold is back to more than $20,000 and more than 200 transactions, and both have to be met, so a couple of bookings won’t trigger one. If a form arrives anyway, keep it with your records and tell your preparer.

Talk to MyCleverCPA before you book summer 2027

We’ll count your personal-use nights against the rental nights, tell you whether the 14-day exclusion actually applies to your house, and sort out who is collecting the county occupancy tax and the sales tax so nothing lands on you in April. See our tax preparation and planning in Sag Harbor.

Call (516) 845-9969 or use our contact page to set up a short call. We’re at 30 Lincoln Street in Sag Harbor.

If you also own a business out here, our post on fixing S corp payroll before December 31 is worth ten minutes this month. And if you hire a caretaker or cleaner for turnovers, that’s payroll and tax compliance territory too.

This article reflects federal, New York State, Suffolk County, and local town and village rules as of October 2026. Talk to a tax professional about your situation.

The 14-Day Rule: When Hamptons Rental Income Isn’t Taxed