Beside Fort Pond
Sunrise-facing mornings
Three apartments

Wake up to Montauk.

The Squarerigger is a historic Montauk home with three private apartments beside Fort Pond. Expect calm sunrises, salty air, and an easy rhythm that makes the days feel longer.

Choose your apartment
At a glance
Three stays. One classic Montauk setting.

Ideal for friends, families, and small groups who want lake-side mornings and easy access to beaches and town. Each apartment is separate, with its own living space and personality.

Fort Pond sunrises Watch first light across the water, coffee in hand, before the day begins.
Montauk energy Beach days, boat time, and that end-of-the-island feeling you cannot fake.
Historic roots Originally a schoolhouse, meeting house, and fire department, now reimagined for stays.
Lake-side calm Quiet water, pastel skies, and the kind of morning that resets you.
Beach days Surf, sand, and sunset drives at the edge of Long Island.
Choose your size 3BR, 2BR, or 1BR depending on your crew and your pace.
All-season Summer sun, fall surf, winter quiet, spring light.
Stay options

Three apartments at the Squarerigger

Port (3-bedroom, 2-bath), Starboard (2-bedroom, 1-bath), and Fo’c’sle (1-bedroom, 1-bath), all beside Fort Pond.

Port

A bright, comfortable 3-bedroom retreat made for full-house weekends and sunrise coffee with Fort Pond right there.

3 bedrooms
Sleeps up to 6
Sunrise views
View on Airbnb
Starboard

A well-appointed 2-bedroom stay with that Montauk morning feeling, light, air, and Fort Pond views that make you slow down.

2 bedrooms
Sleeps 4+
Pondfront vibe
View on Airbnb
Fo’c’sle

A snug, calm 1-bedroom base for couples and solo resets, early sunrises, long walks, and a quiet return at night.

1 bedroom
Sleeps 4
Off-season perfect
View on Airbnb
The house

A Montauk original with a real past

The Squarerigger is more than a place to sleep.

Historic detail

A building with local roots, restored for modern stays while keeping its story intact. It has served the community in different ways. Originally used as a schoolhouse, meeting house, and fire department, it's been part of Montauk’s daily life for generations. Today, it offers that same feeling of shelter and belonging, with the comfort guests want.

Year-round

What to do in every season

Montauk isn’t just a summer town. Each season has its own vibe, and the Squarerigger makes a great base for all of them.

Spring

Longer light, quieter roads, and the first real outdoor days.

  • Morning walks by Fort Pond, then coffee in town
  • Hikes and viewpoints with crisp air
  • Easy beach days before summer crowds
Summer

Full Montauk energy: ocean days, boat time, and late dinners.

  • Surf and swim, then sunset drives
  • Marinas, fishing, and salty afternoons
  • Night walks back at the house under big skies
Fall

The locals’ favorite: warm days, cool nights, slower pace.

  • Beach walks with room to breathe
  • Golden-hour hikes and coastal viewpoints
  • Sunrise mornings that feel cinematic
Winter

Quiet Montauk: dramatic skies, empty beaches, real rest.

  • Cold-weather beach walks and lighthouse runs
  • Cozy nights in, books, board games, movies
  • Photography, stargazing, reset weekends
Local guide

Why Montauk

Montauk sits at the eastern edge of Long Island, where ocean, bay, and open sky meet. Come for the beaches and fresh air, stay for the nature, the food, and the feeling that you’re truly out here.

Iconic views

Take a drive to the Point, walk the bluffs, and let the horizon do its thing.

Parks and trails

Hike, bike, wander. Montauk is built for mornings outside and long walks.

Ocean days

Swim, surf, sunbathe, or just walk until your head clears. The beach always works.

Good to know

FAQ

Are the apartments separate?

Yes. The Squarerigger has three distinct apartments: Port (3BR), Starboard (2BR), and Fo’c’sle (1BR).

Is Montauk worth visiting in the off-season?

Absolutely. Fall and winter are quieter and ideal for long walks, hikes, and reset weekends.

How do I choose which apartment?

Port is best for larger groups, Starboard for families and friends, and Fo’c’sle for couples or solo stays.

Do you offer direct booking or only Airbnb?

New guests are encouraged to book via Airbnb. Returning guests and long term renters may contact us directly. Rates and policies may vary slightly by channel.

What’s included in the nightly rate?

Your stay includes linens, towels, stocked essentials (soap, paper goods), Wi-Fi, and access to shared outdoor amenities where applicable.

Do you require a security deposit?

Depending on booking channel and length of stay, we may place a refundable hold or require a deposit for incidentals and damages.

Are long-term rentals or monthly stays available?

Yes. Message us with your dates and we’ll confirm availability, pricing, and a mid-stay cleaning option if you’d like.

Contact

Reach out

For questions, special requests, or longer stays:

Booking