Suffolk occupancy tax and sales tax
Suffolk County charges a 5.5 percent hotel and motel occupancy tax on short-term lodging of under 30 days, and the rule expressly reaches residences, tourist homes, cottages, and the like, web-verified through the Suffolk County Comptroller. New York State and Suffolk County sales tax, a combined 8.625 percent, can also apply to taxable short-term occupancy depending on the services the rental provides. A full-season or monthly lease is structured differently from a sub-30-day stay, which is one reason the season convention exists, and the tax treatment is a question to settle with the broker and your own counsel before signing. The 2 percent Peconic Bay Community Preservation Fund charge that people mention is a transfer tax on a purchase, not a tax on a rental.
Private chef: $900 to $1,500 per service plus food
An in-house chef in the Hamptons runs $900 to $1,500 per dinner service plus food at cost for a group of ten, with food landing at $90 to $200 per head given the local sourcing. A summer week of four chef dinners and a clambake runs $9,000 to $16,000 all in. The best chefs are booked for the full season by spring, so a one-week August booking competes for the talent the season tenants have already locked.
House staff: $4,000 to $12,000 a week
A daily housekeeper, a house manager, and grounds and pool service on a summer estate run $4,000 to $12,000 a week depending on the size of the property and whether staff are live-in. Many season leases fold the grounds and pool maintenance into the rate but bill utilities and any additional staffing on top. Confirm what the lease covers, because the gap between a bare-house rate and a fully-staffed one is one of the largest on the bill.
Manhattan transfers: seaplane $700 to $1,200 a seat, car from $1,200
A seaplane or helicopter from Manhattan to East Hampton runs 35 to 45 minutes and $700 to $1,200 per seat, weather permitting, the fast way past the Friday traffic. A private car for the 95-mile run runs from $1,200 round trip and 2 to 4-plus hours depending on the departure window, web-verified. The Hampton Jitney and the Long Island Rail Road are the ground alternatives. Budget the seaplane only as a weather-dependent option, never the sole plan.
Beach and club access: $1,000 to $10,000 for the season
Public beach access is parking-permit gated for non-residents, and the private beach and tennis clubs run on membership, not nightly entry. A season cabana or club arrangement, where a rental can secure one, runs $1,000 to $10,000 and more. An oceanfront house with its own beach access avoids the question entirely, which is part of what the oceanfront premium buys.