Nantucket, Massachusetts
Pick Your Island Getaway
Four ways to stay on one set of grounds — hover or tap an option to see it on the map.
All three houses on one set of grounds — the whole place for a big, multi-family gathering.
See the whole compound
A Nantucket compound
Three houses on the prettiest grounds on the island
Milk Street Ext is a three-house compound on Nantucket, Massachusetts, set right on the Cisco bike path between downtown Nantucket and Cisco Brewers, with the island's south-shore beaches a short ride on. It's the rare Nantucket rental where a large group can spread out across three full homes and still share one set of private grounds.
Come for a week of beach days and bike rides, a family reunion, or a wedding weekend that needs room for everyone — then trade the crowds of town for a heated pool, deep gardens and long evenings around the fire.
Big gatherings
Multi-family trips, reunions and milestone celebrations that want the whole compound and its heated pool, barn and game room.
Smaller groups
Couples and small families who want the garden guest house — an outdoor kitchen, a fire pit and quiet borders — without a whole estate.
The whole party
Take all three houses together and put everyone on one set of private grounds, with room to gather and room to slip away.
One house or the whole compound
Compare the houses
Rent any one house on its own, pair two for a pool and room to spread out, or take the whole compound for one large group. Here is what each option gives you.
The grand main house — pool, barn, game room and gym, with room for a group of twelve.
- Sleeps
- 12
- Bedrooms
- 7
- Baths
- 5
- Rating
- 5.0· 54 reviews
The intimate garden guest house for smaller groups — gardens, an outdoor kitchen and a fire pit.
- Sleeps
- 13
- Bedrooms
- 6
- Baths
- 2
- Rating
- 5.0· 60 reviews
The owners’ own house, opened to guests — the most personal rooms on the compound, full of the family’s captain’s collection, with a private pool and cabana of its own.
- Sleeps
- 2
- Bedrooms
- 1
- Baths
- 1.5
- Rating
- —
All three houses on one set of grounds — the whole place for a large, multi-family gathering.
- Sleeps
- 27
- Bedrooms
- 14
- Baths
- 8.5
- Rating
- —
Two houses, one pool
The Mini Compound
The Crew + Captain’s Quarters
Captain's Quarters is the owners' own cottage next door, and it books only together with The Crew — so the two go as one Mini Compound. Take the garden guest house and the cottage together and you get a private pool of your own and room for 15 — even more than the 12 the main house sleeps. It's the main-house experience — the space and a pool — split across two cozier houses on the same grounds.
- Sleeps
- 15
- Bedrooms
- 7
- Baths
- 3.5
Private pool included
Renting the whole compound?
Booking all three houses puts up to 27 guests on one set of grounds. Reach out about each house and we'll coordinate the dates.
The whole place
The Compound
Take all three houses and the grounds are yours — endless space to create endless memories for you and your family.
three houses
Two pools
including one set up for pool volleyball
Huge yards
for bocce, cornhole, or a whole family reunion
Three outdoor kitchens
so the cooking spreads out across the grounds
What's included
Everything on the grounds
The houses share one set of grounds and everything on them. Here's what you can count on, whichever house you book.
Three houses, one compound
All three homes share a single set of private grounds — take one, or the whole property for a big group.
Two pools & a cabana
Two pools on the grounds — Stowaways' heated pool and Captain's Quarters' own private pool with its cabana — one set up for pool volleyball.
Barn & game room
A barn and game room for rainy afternoons and after-dinner tournaments.
Movie room
Stowaways' movie room has a big screen, a wraparound sectional and a stocked candy rack for a night in.
Home gym
Keep your routine without leaving the property.
Outdoor kitchens & fire pits
Three outdoor kitchens across the grounds and three fire pits for long evenings.
Bikes on the Cisco path
The compound is right on the Cisco bike path, and bikes are provided for the ride into town or down to the beach.
Car rental partner
A local partner can have a car waiting — just ask when you inquire.
Concierge on request
Provisioning, reservations and trip-planning help are available on request.
Where you'll be
Location & the grounds
All three houses sit together on the Cisco bike path, about halfway between downtown and Cisco Brewers, with the south-shore beaches a short ride on. Whichever house you book, this is the setting.
- At the door
- Cisco bike path
- 5 min ride
- To downtown
- 10 min ride
- To Cisco Beach
Downtown Nantucket
5 min ride
Cisco Brewers
A short ride down the path
Cisco Beach
10 min ride
Bikes are provided for the ride into town or down to the sand. Need a car for the week? Our local rental partner can have one waiting — just ask when you inquire.
Hosted by Mary-Jo & Tom
Good to know
Frequently asked questions
Can I rent just one house, or do I have to take the whole compound?
Either works. Stowaways, The Crew and Captain’s Quarters each book independently, so you can take one on its own — or reserve all three and have the whole compound to your group.
Are the houses on the same property?
Yes. Stowaways, The Crew and Captain’s Quarters sit together on one set of private grounds at Nantucket, Massachusetts, so a larger party can spread across the houses and still gather in one place.
How many guests does each house sleep?
Stowaways sleeps 12 across 7 bedrooms and 5 baths. The Crew sleeps 13 across 6 bedrooms and 2 baths. Captain’s Quarters sleeps 2 across 1 bedrooms and 1.5 baths. Booked together, the compound hosts up to 27.
Are bikes included?
Yes — the compound sits right on the Cisco bike path, and bikes are provided so you can ride into town or down to the beach without a car.
How far is it to town and the beach?
The compound is on the Cisco bike path, about 5 min ride to downtown Nantucket and 10 min ride to Cisco Beach, with Cisco Brewers roughly halfway between.
Is there a pool?
Yes — two, in fact. Stowaways has a heated pool on the shared grounds, and Captain’s Quarters has its own private pool and cabana. The grounds also have three fire pits, plus a barn, a game room and a gym.
Can you help plan our stay?
We can. Trip-planning and concierge help — provisioning, a car rental through our local partner, recommendations and reservations — are available on request; just mention what you need when you inquire.
How do I book, and is there a minimum stay?
Send an inquiry through any house's page and we'll confirm dates and details by email. The typical minimum stay is 3 nights; reach out if your dates are tight and we'll see what we can do.