Milk Street Ext · Nantucket, Massachusetts
Your Nantucket compound
Three homes on one set of private grounds on the Cisco bike path — book one, two, or all three.
Four ways to stay
Pick Your Island Getaway
Choose an option to see it on the map, or tap a house to explore it.
- One houseThe CrewFor the whole gang.13guests
- One houseStowawaysRoom to settle in.12guests
- Two housesHummock HideawayTogether, with a little more privacy.15guests
- All three housesThe FleetThe ultimate Stowaways takeover.27guests
All three houses on one set of grounds — the whole place for a big, multi-family gathering.
A Nantucket compound
Three homes, endless ways to stay
Three full homes share one set of private grounds on Milk Street Ext, Nantucket, Massachusetts, right on the Cisco bike path between downtown Nantucket and Cisco Brewers, with the south-shore beaches a short ride on. It's the rare Nantucket rental where a big group can spread out and still share the pools, gardens and fire pits.
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 long evenings around the fire.
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.
Expansive private grounds
Lawns, gardens and room to spread out between the houses, all private to guests.
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 two fire pits for long evenings.
Outdoor dining & entertaining
Outdoor tables for long dinners together, whether it’s one house or the whole group.
Beach, Cisco & town access
Halfway between downtown and Cisco Brewers, with the south-shore beaches a short ride away.
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.
One house, two, or all three
Compare the ways to stay
Even the single houses come with serious outdoor space. Here's what each option includes, side by side.
For the whole gang.
- Sleeps
- 13
- Bedrooms
- 6
- Baths
- 2
- Houses
- 1 house
- Private pool
- Not included
- Outdoor kitchen
- Kitchen + bar
- Fire pit
- Stone flame bar
- Games & entertaining
- Not included
- Lawn & play
- Garden + hammock
Room to settle in.
- Sleeps
- 12
- Bedrooms
- 7
- Baths
- 5
- Houses
- 1 house
- Private pool
- Heated, private
- Outdoor kitchen
- Porch grill
- Fire pit
- Not included
- Games & entertaining
- Sports bar barn, movie & game room, gym
- Lawn & play
- Play yard + ping-pong
Together, with a little more privacy.
- Sleeps
- 15
- Bedrooms
- 7
- Baths
- 3.5
- Houses
- 2 houses · The Crew + Captain’s Quarters
- Private pool
- Heated, swim-up spa
- Outdoor kitchen
- Kitchen, bar + cabana bar
- Fire pit
- Two fire pits
- Games & entertaining
- Pool volleyball
- Lawn & play
- Croquet lawn + hammock
The ultimate Stowaways takeover.
- Sleeps
- 27
- Bedrooms
- 14
- Baths
- 8.5
- Houses
- 3 houses · the whole compound
- Private pool
- Two heated pools
- Outdoor kitchen
- Three outdoor kitchens
- Fire pit
- Both fire pits
- Games & entertaining
- Everything on the grounds
- Lawn & play
- Every yard + play area
Where you'll be
On the Cisco bike path
Halfway between downtown and Cisco Brewers, with the south-shore beaches a short ride on. Bikes are provided, and our local rental partner can have a car waiting. Just ask when you book.
- Cisco bike path
- At the door
- To downtown
- 5 min ride
- To Cisco Beach
- 10 min ride
Hosted by Mary-Jo & Tom
All three houses · Up to 27 guests
Take the whole compound with The Fleet
Two pools, three outdoor kitchens and every house to yourselves. Built for reunions, weddings and retreats.
Getting around · From the same hosts
Add a Bronco to your stay
Our sister company, Grey Lady Rental Co, rents a 2025 Ford Bronco Nantucket Edition with the Sasquatch package, ready to drive straight onto the island's beaches. Mention you're staying with us when you reserve.
- Oversand beach permit included
- Great Point, Coskata & Smith Point ready
- Removable hard top & roof rack
- Unlimited mileage, pets welcome
Ready to plan your stay?
Check availability, tell us about your group and we'll confirm pricing by email. Questions first? See the FAQ.
Book a Stay