You can Google “Hamptons summer rental” and get a number. What you won’t find is what it actually costs to live the life those rentals promise. The private chef. The beach club. The right surf camp for your kid. The landscaping that keeps your hedges from becoming a neighborhood scandal.
This guide strips away the vague “it depends” answers and delivers the specific numbers that separate Hamptons insiders from everyone else. Consider it the pricing intelligence you’d get from a well-connected friend who’s been summering out East for twenty years.
The House: What Summer Rentals Actually Run
The rental market has fundamentally shifted since COVID. According to CNBC reporting, summer rentals are down 30% from previous years, with ultra-high-end properties seeing drops between 50% and 75%. Thousands purchased Hamptons homes during COVID’s low-rate window, and 75% of pandemic-era buyers now rent their properties rather than sell.
2026 Rental Price Tiers
Entry-level (Hampton Bays, Springs): $50,000-$75,000 for a 3-bedroom without pool for the Memorial Day to Labor Day season. Springs offers the best value-to-location ratio, pricing 30-40% below East Hampton Village for comparable properties.
Mid-market (Sag Harbor, Bridgehampton): $150,000-$225,000 for a 4-bedroom with pool. Sag Harbor properties move faster than comparables elsewhere due to year-round village appeal.
Premium (Southampton Village, East Hampton Village): $250,000-$500,000 for turnkey properties with heated pools, finished basements, and walkable locations.
Trophy oceanfront: $900,000+ for the season, with some properties commanding $2 million per month for exceptional waterfront estates on Further Lane or Meadow Lane.
Timing matters more than ever. Landlords with unrented properties drop prices 10-20% as summer approaches. Properties listed at $200,000 in February are now negotiable at $160,000-$175,000. July outperforms August in rental activity, a shift from traditional patterns.
The Private Chef: From Dinner Party to Full-Season Staff
The private chef question separates casual renters from serious Hamptons players. Here’s how the economics actually work.
Per-Event Pricing
Services like Take a Chef offer per-person pricing: $100-$175 per guest depending on group size. A dinner party for 8 runs approximately $900-$1,400 including shopping, cooking, serving, and cleanup. Larger gatherings of 13+ average $100 per person. Expect to pay $170 per person average in East Hampton for a customized multi-course experience.
Full-Season Private Chef
This is where the real numbers get interesting. According to salary data and BuzzFeed reporting on Hamptons private chefs, full-season salaries range dramatically: $70,000 on the low end to $500,000 for experienced chefs serving billionaire families. The median sits around $90,000-$120,000 for the season.
Elite placement agencies like Montclair Chef specialize exclusively in ultra-high-net-worth families across Further Lane and Georgica properties. These placements include chefs experienced in Sag Harbor yacht provisioning and multi-residence coordination between NYC, Aspen, and Palm Beach properties.
What a full day looks like: Breakfast, lunch, and dinner averages a 3-4 hour work day, varying with guest count and menu complexity. Schedules flex around client needs, sometimes planned a week ahead, sometimes day-by-day.
Beach Club Access: The Hidden Status Markers
The Hamptons beach club landscape divides into two worlds: places that take your money and places that require your pedigree.
Gurney’s Montauk: The Accessible Option
Gurney’s operates the only on-beach dining experience in the Hamptons open to non-members. Their Beach Club offers cabanas accommodating up to 8 guests with private daybeds, picnic tables, and beach chairs. Lounge daybeds near the DJ booth accommodate up to 6 guests. Pricing requires direct inquiry through their request form, but expect premium rates during peak summer weekends. Resort rooms start around $588/night in low season, climbing past $1,400 during peak periods.
The Elite Private Clubs
Maidstone Club, the Bathing Corporation of Southampton, the Meadow Club, National Golf Links, and Shinnecock Hills Golf Club represent the five most elite private clubs in the Hamptons. These institutions don’t sell memberships; they accept applications from people with the right lineage and connections. Maidstone initiation fees are estimated between $500,000 and $1 million, though the club doesn’t publicly list pricing because, as the saying goes, if you have to ask, you can’t afford it.
Discovery’s Dune Deck Club
For those with significant capital but without generational Hamptons ties, Discovery Land Company’s Dune Deck Club offers an alternative. Beach club membership starts at $350,000. Lodging memberships granting access to 33 Beach Club Suites run $1 million. The club operates Memorial Day through Labor Day with limited hours before and after season.
Golf Club Economics: Where Money Meets Old Money
Four Hamptons courses rank in Golf Digest’s Top 40: Shinnecock Hills (#4), National Golf Links (#8), Friar’s Head (#15), and Sebonack (#39). Maidstone ranks #67. Accessing them requires understanding the two-tier system.
Old-Line Clubs
Shinnecock, National, and Maidstone maintain relatively low initiation fees (under $75,000 historically) but require social pedigree that unlimited checkbooks can’t purchase. Shinnecock’s green fee runs approximately $350 per round for those fortunate enough to secure an invitation. Donald Trump was a temporary member at Maidstone in the early 1980s but was denied permanent membership.
New Money Alternatives
The Bridge (Bridgehampton): $550,000-$1,000,000 initiation. Contemporary glass clubhouse, jeans and backwards caps welcome. Low membership density means rarely crowded rounds.
Sebonack (Southampton): $550,000 initiation. Jack Nicklaus and Tom Doak design with panoramic water views.
East Hampton Golf Club: $260,000-$400,000 initiation.
Friar’s Head (Baiting Hollow): $250,000 initiation. Considered comparable to Shinnecock and National in course quality.
Noyac Golf Club (Sag Harbor): $100,000-$150,000 initiation. More family-oriented atmosphere.
Getting Your Kid Into the Right Surf Camp
Surf camp selection in the Hamptons signals more than athletic interest. It indicates which social circles your family moves in and whether you understand local culture.
Surf Camp Options
Hamptons Surf Co.: Led by professional surfer Kurt Rist, offering daily lessons and camps. Pro surfers provide instruction at premium surf beaches in Southampton and Bridgehampton, with locations chosen based on daily conditions.
Loving Adventures Surf Camp (Amagansett): Monday-Friday, 9am-12pm at Atlantic Drive. Ages 7-14. Features 2:1 student-to-instructor ratio with first-aid certified watermen and waterwomen. Financial aid available for families who qualify.
Austin’s Surf Camp (Montauk): Run by Montauk native and pro surfer Austin Avery Eckardt at Ditch Plains. The original local’s choice.
Expect to pay $25-$40 per hour for private lessons, with week-long camps running $500-$1,200 depending on daily duration and instructor-to-student ratios.
Summer Nanny Economics
Full-time Hamptons summer nannies command $1,500-$2,100 per week for live-in positions, translating to $35-$40 per hour. Many Manhattan families bring their regular nanny out East, requiring additional housing arrangements. Weekend nannies (Friday-Sunday) in the Hamptons earn $40/hour with guaranteed 30-35 hours.
Au pairs offer a more economical option at approximately $195-$250 weekly stipend plus room, board, and agency fees totaling $21,000-$27,000 annually. The limitation: 45 hours maximum per week, making them insufficient for heavy entertaining schedules.
Dining: The Real Cost of Being Seen
Restaurant selection in the Hamptons is less about food and more about positioning. Where you eat signals who you are.
The Power Tables
Nick & Toni’s (East Hampton): The 36-year institution remains the most sought-after reservation in the Hamptons. Ed Burns and Christy Turlington spotted regularly. Menu prices: salads $22-$28, pastas $28-$36, wood-fired whole fish market price. They now offer a two-course prix fixe Sunday-Thursday at $32 per person. Bread basket costs $8.
Sant Ambroeus (East Hampton & Southampton): The Milan import owns the Aperol spritz and people-watching scene. Fifty seats, Loro Piana fabric banquettes, dim lighting from sconces and candles. Perfect pasta, refined eggplant parmigiana. Expect $75-$150 per person before drinks.
Budget per dinner (two people, wine, tip): $250-$400 at top establishments. A weekend of proper dining easily runs $1,500-$2,500.
Property Maintenance: The Costs Nobody Mentions
Owning or renting in the Hamptons comes with maintenance obligations that separate serious players from weekend tourists.
Pool Service
Weekly pool maintenance from established services like Hampton Pool Company or Tri-M Pool Care runs $150-$350 per week depending on pool size and chemical requirements. Season opening: $400-$600. Season closing: $400-$600. Heated pools add significant costs to utilities.
Custom gunite pool installation ranges from $40,000-$60,000 for basic designs to $60,000-$90,000 for customized features like lighting, tiles, and water elements. Premium installations with full landscape integration exceed $150,000.
Landscaping
Full-service landscape maintenance from firms like Groundworks, Harmonia, or Mahoney Associates includes irrigation, lawn care, tree pruning, and tick control. Monthly maintenance for a 1-2 acre property runs $2,000-$5,000 depending on complexity. Tick and mosquito control applications occur multiple times throughout season.
Landscape design and installation for pool areas and outdoor living spaces: $50,000-$200,000 depending on scope. A Sagaponack client recently received rental income increase equal to the cost of a new gunite pool, patio, and outdoor kitchen within one summer.
Fitness and Wellness: Maintaining Appearances
Equinox Hamptons: 3-month non-member access runs $750/month. Season access (Memorial Day through Labor Day) costs $700/month. Individual group fitness classes for non-members: $60 per class. Class booking opens one week in advance.
Private pilates, yoga, and personal training sessions command $150-$300 per hour with sought-after instructors booked weeks in advance during peak season.
The Real Calculation
A “modest” Hamptons summer for a family of four renting in Hampton Bays with minimal staff and occasional dining out runs $80,000-$120,000 all-in. A proper Southampton Village experience with private chef, club memberships, and appropriate maintenance easily exceeds $500,000 for the season.
The difference between tourists and residents isn’t just money. It’s knowing which numbers matter, which clubs to pursue, and which expenses signal sophistication versus desperation. This guide provides the intelligence. The application is up to you.
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