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Four white chairs on a lawn above the water. The reunion week is mostly this: a big house, a lawn, and the people you came with.
A family reunion on Martha's Vineyard: what a whole-family house costs with the 11.7 percent tax and cleaning fee, why bedrooms decide how many it sleeps, the cheaper alternatives, walking twenty people onto the ferry instead of bringing cars, feeding the group, the one restaurant night to book a year out, and the free week.
A family reunion on Martha’s Vineyard is a wonderful idea and an expensive one, and the difference between the two is made in January. The island’s big houses are rented by the week, Saturday to Saturday, and the ones that genuinely sleep fourteen are gone for August by early spring; the restaurants that can seat forty book a year out; the car ferry sells its summer weekends within hours of opening in February. Get those three things right and the rest of the week runs itself: the bus is free, the beaches are free, the sunsets get applause, and there is a carousel older than the Statue of Liberty for the cousins. This is our guide to doing it properly: what a house for the whole family actually costs with the tax and the cleaning fee on top, the honest alternatives when a single house will not do, how to move eighteen people onto the island without eighteen cars, where to feed them, and the one night out that everyone will remember.
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The island’s vacation rentals are old houses, and old houses have their own arithmetic. Septic systems are sized for a number of bedrooms, and the towns now cap occupancy to match; Oak Bluffs’ draft rule is two people per bedroom plus two. A house that sleeps eight is not a house for a reunion of fourteen, whatever the sofa bed suggests, and an agency will say so. For a big family the honest choices are one large house of five or six bedrooms, which exist mainly up-island and in Edgartown and start well above $10,000 for an August week, or two smaller houses within walking distance of each other in a village, which is often cheaper, gives the generations their own front doors, and is easier to find. Book through the island agencies (Tea Lane and Sandpiper up-island and in Edgartown, MV Vacation Rentals in Vineyard Haven, Ocean Park Realty in Oak Bluffs) or the platforms, and read our rental guide for the lease terms, the town registrations and the scams before you wire a deposit. Ask what is in the shed: some owners leave bikes, kayaks, beach chairs and a grill, and for twenty people that is real money.
The stair hall of a captain’s house in Edgartown. The island’s big rentals are houses like this: old, handsome, full of stairs, and sized by their bedrooms, not their sofas.
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The Camp Meeting Association rents a four-bedroom, two-bath apartment inside the Oak Bluffs Campground by the week, Saturday to Saturday, June through mid-September, at $3,500 to $4,025, plus three one-bedrooms at $1,750 to $2,100. The quietest address in Oak Bluffs and the cheapest big unit on the island. Booking for 2027 opens in October.
A condo-hotel steps from Main Street where every studio and one- or two-bedroom unit has a full kitchen, with a pool, a playground and free parking, from about $160. Book a block of units and the family has its own doors and a shared pool.
Fifty-one units in Oak Bluffs with a pool, tennis and a playground, $350 to $550 and up: the resort option for a family that would rather not cook every night.
The Franklin Hotel in Edgartown has a penthouse loft that sleeps six, one of the few in-town setups for a larger family without renting a house.
The Winnetu at Katama, $925 to $995 in season, the closest resort to South Beach, ten to fifteen minutes over the dunes on foot. The splurge, with the beach thrown in.
The where to stay guide has every one of these with the current rates and the walk to the ferry.
A backyard deck over the water in Vineyard Haven, table and chairs waiting. This is the reunion dining room; the restaurants are for one night.
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Do not bring the cars. One vehicle on the Steamship Authority is $127 midweek or $168 on a summer weekend each way, its reservation opens in early February and the weekend slots go within hours, and standby has been suspended since November 2024. Everyone else walks on for $11 with no reservation at all, and from the terminal the fare-free VTA buses reach every town, the big beaches and the airport. Bring one car for the grandparents and the grocery run, or leave it at Woods Hole and rent one on the island for the two days you need it; our car rental guide has the agencies and the van options. Coming from far away, the ferry guide covers the boats from Falmouth, Hyannis, New Bedford and New York, and the bus page gives every route and minute. A reunion arriving over two days on the boats from different cities is normal here; the Vineyard Haven terminal is the meeting point.
Know Before You Go
Stop & Shop at 50 Water Street in Vineyard Haven is across from the ferry; send two people with the car straight there. Or use Ahead of Arrival, the island service that shops and stocks the house before you land; our grocery guide has the stores, the prices and the delivery zones.
Buy off the boat in Menemsha or at the fish markets and cook at the house. Grace Church in Vineyard Haven sells lobster rolls on Friday evenings, May to September, for about $20, and takes a crowd without a reservation.
Book it the summer before. The wedding guide is blunt: a party of forty in season is arranged a year out. For a smaller table, Nomans in Oak Bluffs has lawn games, live music and a free shuttle from the harbor, and Sharky’s stays open late with a kids’ menu.
Tilton Tents and Party Rentals in Vineyard Haven does tents, tables, chairs, linens and lighting, and the island’s caterers are the same people who do its weddings. Twenty people under a tent on the lawn beats any restaurant.
The Vineyard Preservation Trust rents the Old Whaling Church, Union Chapel, the Grange Hall and the Daniel Fisher House for parties. A fiftieth anniversary in the Daniel Fisher garden is the kind of night people fly in for.
A tent on the lawn of the Daniel Fisher House on Main Street in Edgartown, one of the landmarks the Preservation Trust rents for parties. The reunion dinner with a roof over it.
Know Before You Go
State Beach, calm and shallow with the bus stopping along it, or the Inkwell in Oak Bluffs. A group of more than fifty, or anything with a caterer, needs a permit from the county for the state beach. Up-island houses often come with a beach sticker; West Tisbury renters get Lambert’s Cove.
The three-hour narrated island tour from Oak Bluffs, about $55 to $70 a person, is the one afternoon that shows the grandparents and the teenagers the whole island without anyone driving.
A private charter takes six for $500 on a two-hour sunset cruise; the MV Skipper party boat takes a crowd fishing for $100 a head, gear included. Split the family across two sailings and compare catches at dinner.
Menemsha, from the beach by the fish markets, where the crowd applauds. Bring the lobsters and the chairs and make it the first night.
The Agricultural Fair in West Tisbury returns in August 2027 (dates post in spring), Grand Illumination Night in the Campground is a Wednesday in mid-August, and the Sunday band concerts, Tuesday dock dance and Wednesday community sing are free all summer. Our August guide and September guide cover the two months most reunions pick.
A backyard at dusk, pink sky over the fence. The nights of a reunion week happen here, not in town, and the town rules say quiet after ten.
The island is a place where people live, and a house with twenty people in it is noticed. Quiet after 10 PM, cars in the driveway and not on the verge, no fireworks (illegal in Massachusetts), trash bagged and windows shut at departure by 10 AM, and a tick check on every child every night; the rules and etiquette guide and the tick guide are the two pages to send to the group chat. Up-island, West Tisbury, Chilmark and Aquinnah restaurants serve beer and wine only with meals and Chilmark sells no alcohol at all, so the package store run happens in Oak Bluffs or Edgartown before you head up. Price the whole week for your own family, with the house, the boat and the one restaurant night, in the trip cost calculator; our budget guide and family guide fill in the rest.
Step 1 · WhenMonth PickerTwelve months compared on NOAA numbers, crowds, prices and what is open. 
Step 2 · DaysDay-by-Day Trip PlannerMorning, afternoon and evening sketched for every day, events dropped in, emailed to you. 
Step 3 · CostTrip Cost CalculatorFerry, beds with the rooms tax, meals, getting around and activities in one honest range. Our own footage, so the family can see where the house is.
Four or more bedrooms in peak season start around $6,000 a week and in-village Edgartown or waterfront houses in August commonly run $12,000 or more, plus 11.7 percent tax on the rent and the cleaning fee, a $650 to $1,000 cleaning fee and linens. June and September are 30 to 50 percent lower. The Campground’s four-bedroom apartment at $3,500 to $4,025 a week is the cheapest big unit on the island.
Rarely, and the towns now cap occupancy by bedroom (Oak Bluffs’ draft rule is two per bedroom plus two), because the septic systems are sized that way. Two houses within walking distance in a village is the usual answer for twenty, and it is often cheaper and easier to find.
No. One car is $127 to $168 each way with a reservation that opens in February and sells out within hours for summer weekends. Walk everyone else on for $11, ride the fare-free bus, and rent a car or van on the island for the days you need one.
At the house, most nights: Stop & Shop is across from the ferry, Ahead of Arrival will stock the house before you arrive, and the fish markets sell lobsters off the boat. For the one restaurant night, book the summer before; the good rooms take a party of forty a year out. A tent, a caterer and the backyard is the reunion dinner that works.
September if the group can travel then: warm water, open businesses, the resident beaches open to all from mid-month and houses 30 to 50 percent below August. Mid-August if you want the Fair and Illumination Night, at August prices and with the house booked by early spring.
Rental price bands, tax, cleaning fees, lease terms and the occupancy rule are from our September 2026 rental guide research (island agency listings, the Massachusetts short-term rental tax tables and the Oak Bluffs draft bylaw); the Campground apartments, Edgartown Commons, the Island Inn, the Franklin and the Winnetu are from the properties’ own 2026 rates; ferry fares are the Steamship Authority’s published 2026 rates; the county beach permit rule is from the Dukes County beach regulations; tour and charter prices are the operators’ September 2026 rates. Book the house and the boat before anything else; both are decided in winter.
Island tip of the day Transport No. 11 of 86 New tip at midnight, island time
Uber and Lyft operate on MV but surge hard in peak season. Local taxis are often steadier: a typical cross-town ride runs about $28, van-pool style, and airport pickups add a small rideshare surcharge.
Martha's Vineyard with teenagers: the free buses and 35 miles of bike path that let them roam, surf lessons, the night glow kayak, jet ski tours, the arcade and mini golf open late, the Jaws locations, Chappaquiddick by bike, the Derby's junior division, the free outdoor music, and the honest notes on ticks, surf, mopeds, the last bus and the rules a rental house lives by.
Martha's Vineyard with a baby or toddler: rent the crib, stroller and car seat from the island service instead of packing them, the three calm beaches with somewhere to change (Owen Park first), the alpacas, the free farm, the platform carousel, a nap-proof day, the town to sleep in, and the honest cautions on ticks, surf and the hospital.
Martha's Vineyard for seniors and slower travelers: the level towns (Oak Bluffs and Vineyard Haven, not Edgartown's brick), the free kneeling buses and the Lift, the ferry's elevators, the beaches with mats and beach wheelchairs, the hotels with lifts, the museum, Felix Neck and Mytoi, the island bus tour, and what we would not pretend is easy.
Oak Bluffs or Edgartown: where to stay on Martha's Vineyard, compared on the ferry (the summer boat lands in Oak Bluffs), room rates ($200 to $400 vs $250 to $450 in August), nightlife (Circuit Avenue to 12:30 vs a 10 PM bylaw), restaurants, beaches, parking, children and couples, with the honest middle answer.
The practical guide for J-1 students, H-2B workers and summer staff on Martha's Vineyard: Social Security sessions at the Oak Bluffs Library, the free bus and its live map, the two laundromats (yes, one is by the airport), cheap bikes, groceries, Wi-Fi, pay rules, health, food help if money runs short, and free days off. Checked September 2026.
The Martha's Vineyard honeymoon guide from a local: the best month to come (September), the eight inns that are actually romantic with 2026 rates, a five-day plan from Edgartown to the Aquinnah cliffs, the dinners worth a Resy reservation, the catboat and tall-ship sails, the dry-town bottle rule, and a worked budget for five nights.
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