Guide
The Nantucket summer rental guide
Everything we get asked before someone books a week here: which week is actually the best one, what a house really costs, whether to take the boat or fly, and where on the island you want to be. Written by people who let a house here, so read it with that in mind — but it is honest, and most of it argues against spending more than you need to.
Which week to book
Nantucket’s season runs from Memorial Day to Columbus Day, and the character of the island changes substantially across it. Most people default to the first two weeks of August, which is a defensible choice and also the most expensive and most crowded one. Here is the honest week-by-week.
Late May and early June
Quiet, green and cheap by island standards. The water is still cold — genuinely cold, not bracing-but-fine cold. Restaurants are opening in stages and some are not yet open at all. Good for a couple, a golf trip, or anyone whose priority is the island rather than the beach.
Mid to late June
The sleeper choice. Daylight is at its maximum — light until past 8:30pm — the hydrangeas and roses are at their peak, the island is fully open, and the crowds have not arrived. The water is swimmable on the harbour side and still brisk on the south shore. If you have flexibility and want value, this is where to look.
The Fourth of July week
Fireworks over Jetties Beach, a proper small-town parade, and the island at full tilt. It is wonderful and it is packed. Book this one the previous autumn or not at all.
Mid-July
Reliably warm, fully open, and slightly less frantic than the weeks on either side of it. A good compromise week that often has availability when the ones around it do not.
Late July to mid-August
Peak. The warmest water of the year, every restaurant open, every table booked, Race Week sailing in the harbour, and the Boston Pops on Jetties Beach. This is the Nantucket of the photographs. It is also the hardest to book and the least forgiving of a late decision.
Late August
The water is at its warmest of the whole year, and once the mainland school year starts the island empties noticeably. An underrated week.
September
The islanders’ favourite month, and it is not close. Warm ocean, empty beaches, mild dry days, restaurant tables available on the night, and the light turns. Rates soften. If you do not have school-age children, book September and thank us.
If you are flexible, mid-June and September give you eighty per cent of an August week for meaningfully less money and considerably less company.
What a Nantucket summer rental actually costs
Weekly whole-house rentals are the norm here; nightly bookings barely exist in season. As a rough guide for a peak-season week:
| Type of house | Typical peak week |
|---|---|
| Two or three bedroom cottage, off-centre | $6,000 – $12,000 |
| Four or five bedroom family house | $15,000 – $35,000 |
| In-town or waterfront house, high specification | $25,000 – $60,000 |
| Trophy waterfront estate | $75,000 and up |
Indicative market ranges for orientation only, not quotes. June and September typically sit ten to thirty per cent below the peak-week figures.
The costs people forget
- Short-term rental tax. Massachusetts levies a state room-occupancy excise on short-term rentals, and Nantucket adds local and regional charges on top. Budget for a meaningful percentage above the headline rent and ask for the exact figure in writing before you sign.
- Cleaning and service fees. Booking platforms routinely add both. A direct booking often does not — ours does not — so compare the total, not the nightly rate.
- Getting the car over. A car ferry reservation in season is expensive and must be booked months ahead. Many guests find hiring on-island cheaper and easier.
- Groceries. Everything arrives by boat. Expect island prices, and consider having the house provisioned before you land rather than losing your first afternoon to a supermarket.
- Damage deposit. Standard practice, refundable, usually held until a week after departure.
For what one house charges and precisely what is inside the number, see our rates and availability page.
The booking timeline that actually works
| When | What to do |
|---|---|
| September – October | Returning guests take their weeks. If you stayed somewhere you liked, this is when to claim it for next year. |
| November – January | The real booking window. Inventory is at its widest and you have genuine choice of week and house. |
| February | Peak July and August weeks disappear. Book flights and ferries now; car ferry slots go first. |
| March – April | June and September still open. Make restaurant reservations for peak weeks. Order beach permits if you want Great Point. |
| May | Late availability appears as plans change. Worth asking even about weeks listed as taken. |
| Two weeks out | Confirm provisioning, chef, bicycle hire and any charters. |
Where on the island to stay
Town
The historic district and the streets immediately around it. You can walk to dinner, to the boats, to the museum and to Children’s Beach, and you can leave the car parked all week. The trade-off is that you are not on the water and gardens are smaller. For most groups — and particularly for anyone who does not want to nominate a driver every evening — Town is the right answer. It is where 20 West Chester Street sits.
Cliff and Brant Point
Just north of Town, a short walk or cycle in, with larger properties and closer access to Jetties and Steps. Quieter streets, higher rents, still walkable to dinner if you are willing to do twenty minutes each way.
’Sconset
A rose-covered village at the eastern end of the island, twenty minutes from Town by car. Beautiful, self-contained and genuinely peaceful, with a handful of its own restaurants. You will drive for everything else, which some people consider the point.
Surfside, Cisco and Madaket
The south and west shores, closer to the big Atlantic beaches and the sunsets. Larger lots, more modern houses, a car essential. Good for surfers and for groups whose day is built around the beach rather than the town.
Monomoy, Shimmo, Polpis and Wauwinet
Harbour-side and eastern addresses, often with private beach access and the biggest houses on the island. Serene, expensive, and a drive from everything.
Getting to Nantucket
The ferry from Hyannis
Two operators run from Hyannis on Cape Cod. The Steamship Authority runs the traditional ferry — about two and a quarter hours, carries cars, and is the only way to bring a vehicle. The Hy-Line fast ferry is about an hour, passengers only. Both dock in Nantucket town, within a ten to fifteen minute walk of most in-town rentals.
Two things to know. Car reservations for July and August open months ahead and sell out; if you want one, book it the day it opens. And the drive to Hyannis on a summer Friday can add hours — travelling Saturday morning, with the changeover, is usually smoother than it sounds.
Flying
Nantucket Memorial Airport (ACK) is ten minutes from Town and takes seasonal direct service from New York, Boston, Washington and other East Coast cities, plus year-round Cape Air hops from Boston and Hyannis. Fog is a genuine variable in June and early July; build slack into a tight connection and do not plan to land at 6pm and make a 7pm reservation.
Which to choose
Flying if you are coming a long way, travelling light, or short on time. The boat if you have a big group, a lot of luggage, or children who will treat the crossing as the start of the holiday rather than an obstacle to it. Arriving past Brant Point Lighthouse on the deck of a ferry is, unarguably, the better entrance.
Do you need a car on Nantucket?
If you are staying in Town: no, and you will probably regret bringing one. Parking is tight, the streets are cobbled and narrow, and everything you need is inside a twenty-minute walk. Hire bicycles for the week — the island’s bike path network is excellent and mostly separated from traffic — and take a taxi the two or three times you go further.
If you are staying in ’Sconset, Madaket or out on the moors: yes. Either bring one on the Steamship Authority or hire on-island, which is generally cheaper than the ferry slot plus the ferry fare once you count everything.
For Great Point and Coatue you need four-wheel drive and an over-sand vehicle permit. Both are arrangeable; neither is spontaneous.
Choosing a beach
| Beach | Water | Best for |
|---|---|---|
| Children’s Beach | Harbour, flat, warm | Toddlers, playground, walk from Town |
| Jetties | Sound, calm | Lifeguards, rentals, food, families |
| Steps | Sound, calm | Quieter than Jetties, sunset, no facilities |
| Surfside | Atlantic, real surf | Teenagers, bike path access, lifeguards |
| Cisco | Atlantic, biggest waves | Surfing and surf school |
| Madaket | Atlantic, strong current | The sunset, strong swimmers only |
| Great Point | Open ocean, currents | Fishing, seals, solitude; permit required |
The rule of thumb: north shore for calm and warm, south shore for waves. On a windy day, whichever shore is downwind will be noticeably more pleasant — and on Nantucket, that is worth checking before you load the car.
Eating, and the reservation problem
Nantucket has an unusually good restaurant scene for an island of its size, and in July and August it is fully booked. The mistake visitors make is treating reservations as a holiday-week task. They are a booking-week task.
- Book your two or three anchor dinners the same week you confirm the house.
- Keep two nights free for the outdoor table — a chef at the house is often better than the restaurant you could not get into.
- Lunch does not need booking. The sandwich places and the fish market carry the middle of the day.
- Bar seating at the best restaurants is frequently walk-in, and frequently the better seat.
Our location page lists what is inside a fifteen-minute walk of the house.
The summer calendar
Worth knowing about when you pick a week, because each of these moves demand and availability.
| Roughly when | What |
|---|---|
| Late April | Daffodil Festival — antique car parade, tailgate |
| Mid-May | Nantucket Wine & Food Festival |
| Memorial Day weekend | Figawi race from Hyannis; the season opens |
| Late June | Nantucket Film Festival |
| 4 July | Parade, water fight on Main Street, fireworks |
| Early August | Boston Pops on Jetties Beach |
| Mid-August | Race Week — the harbour full of sails |
| Early October | Nantucket Cranberry Festival |
| Early December | Christmas Stroll |
Dates move year to year. Check the current schedule before you commit to a week around one of them.
When it rains
It will, for at least one day. Nantucket fog is a real feature of June and early July and can sit over the island for a day and a half. The island handles it better than most beach destinations:
- The Whaling Museum is genuinely excellent and takes two hours easily.
- The Nantucket Atheneum, one of the oldest libraries in the country, is a good rainy hour.
- The galleries and shops on Old South Wharf and Straight Wharf.
- Cisco Brewers, which is entirely undeterred by weather.
- A long lunch, which on a foggy Nantucket afternoon is an acceptable plan for the entire day.
This is also the argument for renting a house with somewhere to sit that is not a bedroom. A porch with a fireplace earns its keep on exactly these days.
What to bring
- A warm layer, more than you think. Evenings drop into the fifties even in August, and the porch is where everyone ends up.
- Shoes for cobblestones. Main Street is beautiful and it is genuinely ankle-turning.
- Rain gear. Not an umbrella — it will be windy.
- Something for one smart dinner. Nantucket is relaxed but not that relaxed.
- Reef-safe sunscreen and a hat. There is very little natural shade on the beaches.
- Not beach chairs, towels or bicycles. Ask your house first — most well-run rentals either provide them or will have them waiting.
Five common mistakes
- Booking too late for July and August. By March you are choosing from what is left, not what you want.
- Comparing headline rates instead of totals. A cheaper weekly rate plus a cleaning fee, a service fee and a platform commission is frequently the more expensive week.
- Bringing a car you will not use. An in-town house makes the car an expensive liability.
- Leaving restaurants until you arrive. Book the anchor dinners when you book the house.
- Ignoring June and September. The two best-value stretches of the season, and September in particular is better weather than most people believe.
The house this guide comes from
20 West Chester Street is a 2016 KMS Design house in the heart of Town — four en-suite bedrooms plus a third-floor playroom, sleeping ten, with a three-season porch that opens on folding glass walls and a bluestone patio backing onto protected woods. It lets Saturday to Saturday at $30,000 per week, booked directly, with no cleaning or service fee.