Westport Point, Massachusetts
A waterfront colonial at Westport Point, in the coastal town of Westport, Massachusetts. Sunrise over the river, sunset over the harbor with sailboats. This is your summer.
The House
A waterfront colonial with modern updates on the Westport Point peninsula. The main house is yours for the summer — wake up to sunrise over the Horseneck bridge flooding into the kitchen, and end the day watching sunset over the harbor with sailboats from the front. Views of both the east and west branches of the Westport River.
You have the run of the main house. The boathouse and barn are ours — you'll see us coming and going for the boats, the lobster traps, the usual summer chaos. The right side of the driveway stays clear for family access. Guest parking is on the left. The large backyard extends to the river.
If you need anything, we're never far. Brothers up the street, family on the water. The Long family is licensed for lobstering, and the dock is an active waterfront all summer. You're not renting from strangers — you're spending the summer with a family that's been on this coast for three generations. That's not a caveat. That's the experience.
We're respectful of your space and you're respectful of ours. But if you want the inside track — where to fish, who to talk to at the dock, where the locals go for dinner, the best spot to watch the sunset — just ask. We've been here a while.
Directly on the water at Westport Point with views of both branches of the Westport River. Sunrise and sunset from the house.
Dock space available at $4/foot/night. Kayaks and canoe available on request. Walk down to the water from the house.
Modern kitchen with gas stove. Everything you need to cook with the fresh catch and farm stand produce Westport is known for.
One king, one room with two doubles, and one double. Three bedrooms, two baths. Comfortable for families and groups.
Large backyard extending to the river. Room to spread out, play, and watch the boats come in. Shared space — the family's summer and yours overlap here.
Brothers up the street, family on the water. If you need anything — a restaurant recommendation, a stuck lock, a lobster — someone is always close.
“Wednesday night folk music at the fishing dock, 100 feet from the house. The oyster bar is walking distance. Sunrise over the bridge into the kitchen. Sunset with sailboats from the front.”
Life at 2042 Main Road
The Fire Pit
When the sun drops behind the harbor and the sailboats go still, the fire pit comes to life. This is where the day ends at 2042 Main Road — with the sound of the water, the glow of the coals, and nowhere you need to be.
Where You're Staying
2042 Main Road sits in the Westport Point Historic District, a designated historic district. The land beneath this house has been walked for centuries. Westport Point was known as “Paquachock” to its Native inhabitants, and Main Road follows what was likely a pre-existing Native American trail down the peninsula to the water.
The Point was settled by the early 1700s. By the mid-1800s, it was a whaling port with twenty to thirty vessels working out of the harbor. During the Revolution, privateer vessels used these waters — the sandbars at the harbor mouth made it nearly impossible for outsiders to navigate, turning Westport Point into a natural stronghold. A fish market building from around 1740 still operates at the Point today.
The Long family has been on this coast for three generations. A grandfather who served thirty years as a Massachusetts State Representative. Letters from Senator Kennedy in the family archive — “Dear Representative and Mrs. Long” on Senate letterhead. 2042 Main Road is where the family gathers: the boathouse, the dock, the fire pit at sunset, the next generation learning to fish off the pier and paddle across the harbor.
When you stay here, you're part of that continuum — a place shaped by centuries of people drawn to this particular stretch of water. This isn't an investment property. It's a family compound that opens its doors for the season, in a historic district that preserves the character of one of Massachusetts' oldest waterfront villages.
Learn more from the Westport Historical Society.
From the family archive — correspondence between Senator Kennedy and the Long family, 1950s
The Location
Westport Point is a small, historic waterfront village at the tip of a peninsula in the town of Westport, Massachusetts — where the east branch of the Westport River meets Buzzards Bay. Lobster boats work the harbor, stone walls line the roads, and summer moves at the pace it should.
The property sits at 2042 Main Road, Westport Point, MA 02791. Walk to the town dock, the fishing pier, the oyster bar. Drive ten minutes to some of the best beaches on the South Coast of Massachusetts. This is Westport at its most genuine — no crowds, no pretense, just the coast.
Westport Point is a walking village. After dinner, Main Road comes alive — families, couples, dogs. Walk up the street to the old graveyard. Walk down to the docks and watch the light change over the harbor. The word for this place is bucolic — rolling, unhurried, gentle. The kind of quiet that makes you slow down without trying.
Things To Do
From Westport Point, you're minutes from beaches, wineries, farm stands, and the best of the South Coast. Here's what a summer in Westport, Massachusetts looks like.
Steps Away
Wednesday night folk music at the fishing dock — 100 feet from the house. Bring a chair, bring a drink, or just listen from the porch.
Walking Distance
Walk to the oyster bar at Westport Point, the town dock, the fishing pier, and Partners Village Store. After dinner, stroll Main Road with everyone else — families, couples, dogs. This is a walking village, and the evening walk is the main event.
Beaches
One of the best beaches in Massachusetts. Miles of sand, strong surf, spectacular sunsets. About a 10-minute drive from the property.
Beaches
A quieter alternative with calm waters — ideal for families with young children. Also just minutes from Westport Point.
Wine & Beer
Award-winning vineyard and winery right in Westport. Tastings, tours, and gorgeous grounds for a summer afternoon.
Wine & Beer
Local craft brewery with a taproom and outdoor seating. A Westport staple.
On the Water
Kayaks and canoe available from the property. Cast a line from the town fishing pier. Dock space for your boat at $4/foot/night.
Local Farms
Westport is farm country. Pick up fresh produce, flowers, and local goods at roadside farm stands throughout the town.
Trails & Conservation
Coastal walks, conservation land, forested paths through working farms. The Westport Land Conservation Trust, The Trustees, and the Buzzards Bay Coalition all maintain public trails nearby.
Explore the Area
From Westport Point, the entire South Coast of Massachusetts and Rhode Island is at your doorstep. Explore the places that make a summer at 2042 Main Road unforgettable.
Summer Availability
Summer 2026 at Westport Point. Select weeks still available in June, July, and August. Westport Point summers fill early — once a week is booked, it's gone until next year.
Guest Reviews
“The hospitality was exceptional from start to finish. The house is warm, welcoming, and clearly cared for. You can feel that this is a family's home, not a rental factory.”
Hospitality · Comfort
“The location is unbeatable — right on the water at Westport Point. We walked to the dock, the oyster bar, and the folk music. Horseneck Beach was a quick drive. Our kids didn't want to leave.”
Location · Walkability · Family
“Waking up to harbor views every morning was something else. The house is comfortable, clean, and beautifully set up. The kitchen had everything we needed, and the indoor spaces felt like home.”
Views · Indoor Spaces · Cleanliness
“Perfect for families. Three bedrooms, plenty of space, and the backyard goes right down to the river. The kayaks were a huge hit. We've already booked again for next summer.”
Family · Comfort · Beach Access
“This isn't a typical Airbnb — it's a real place with real character. The hosts were incredibly responsive, the house was spotless, and Westport Point is one of the most beautiful villages we've ever visited.”
Hospitality · Location · Cleanliness
FAQ
Horseneck Beach State Reservation is about a 10-minute drive from the property. Cherry & Webb Beach is similarly close. Both are among the best beaches on the South Coast of Massachusetts.
Westport Point and the surrounding town of Westport, Massachusetts offer an incredible summer. Walk to the oyster bar, fishing pier, and Wednesday night folk music at the dock — all within steps of the house. A short drive brings you to Horseneck Beach, Cherry & Webb Beach, Westport Rivers Winery, Buzzards Bay Brewery, farm stands, and Partners Village Store. Kayak and canoe from the property, or fish right from the town pier.
Yes. Dock space is available at $4 per foot per night. Kayaks and a canoe are also available on request at no additional charge.
No, pets are not permitted at the property.
Check-in is at 3:00 PM and check-out is at 11:00 AM. Full details are provided after booking through Airbnb. The property has exterior security cameras for guest safety.
Summer is the magic season at Westport Point. June through August offers the best weather for beaches, boating, and exploring the village. The property is available as an exclusive seasonal summer rental — typically June, July, and August, with occasional mid-May availability.
Westport Point is a small, historic waterfront village at the tip of a peninsula in the coastal town of Westport, MA. It's a quiet, residential community where lobster boats still work the harbor, stone walls line the roads, and neighbors wave from porches. Wednesday evenings bring folk music to the fishing dock, 100 feet from the house. The oyster bar is walking distance. This is authentic old New England — not a tourist town.
You have the run of the main house — 3 bedrooms, 2 baths, updated kitchen with gas stove, and views of both the east and west branches of the Westport River. Guest parking is on the left side of the driveway; the right side stays clear for family access. The large backyard extends to the river and is shared space. The boathouse and barn are family areas — you'll see the Longs coming and going for the boats, the lobster traps, the usual summer activity. If you need anything, a family member is always minutes away. You're not renting from strangers — you're joining a family's summer at Westport Point.
Yes. The property is located within the Westport Point Historic District, which preserves the distinctive character of one of Massachusetts' oldest waterfront villages — a place that has been home to fishing communities, whaling fleets, and Revolutionary War privateers since the early 1700s. Learn more at the Westport Historical Society (wpthistory.org).
Yes. 2042 Main Road operates in accordance with Westport's community standards. Westport voters approved a short-term rental bylaw at the 2025 Town Meeting. We are proud to operate in full compliance with the town's guidelines.
2042 Main Road is a residential property in a quiet waterfront village. No parties or commercial events — residential use only. Quiet hours are respected. Maximum 6 guests. Exterior security cameras are in place for guest and community safety. A local emergency contact is available 24/7. We take being part of this community seriously.
The property is listed on Airbnb at airbnb.com/h/2042main. Scan the QR code on this page or visit the listing directly to check availability and book. For questions, message us through the Airbnb listing.
Good Neighbors
The best guests at 2042 Main are the ones who fall in love with the quiet. The harbor at sunset. The folk music drifting up from the dock. The sound of the river. This is what Westport Point sounds like. We ask that you help keep it that way.
Westport Point is a tight-knit waterfront village where the houses are close together and the neighbors are year-round residents. They welcomed short-term rentals back after a hard-fought community process — Westport voters approved a rental bylaw at the 2025 Town Meeting. Honoring that trust matters to us, and it should matter to our guests.
This is not a party house. It's for guests who want to enjoy the coast, the quiet, and the rhythm of a real New England village. Enjoyment is encouraged — this is your vacation. But enjoyment and respect for this community go together here.
Respectful volume at all times. Quiet after 10 PM. The neighbors are close, they're here year-round, and they're the reason this village still feels the way it does.
No parties, no events, no large gatherings. This is a home in a residential village. We host guests who come for the coast, not the nightlife.
Three bedrooms, six guests. The property is sized for families and small groups. Our 4.92-star rating reflects the kind of guests this place attracts.
Exterior security cameras are in place for guest and community safety. No interior cameras — your privacy inside the home is absolute.
A family member is always minutes away. Emergency or otherwise — you're never on your own at Westport Point.
Violations of community standards may result in early termination of the stay. We've never had to enforce this — and we'd like to keep it that way.
This Summer
Reserve your dates at Westport Point. Once a week is booked, it's gone until next year.
Interested in Summer 2027? Message us through the Airbnb listing to get on the list for next season.
Book Your Stay
Scan the QR code to view the listing and book your summer at 2042 Main Road, Westport Point, MA 02791.