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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.
The House
A waterfront colonial with modern updates on the Westport Point peninsula. The main house is yours for the summer. Sit in the front room and you see water in every direction. The harbor and fishing boats to the right, the river wide open straight ahead, Westport Harbor to the west. It's one of those rooms where the light changes all day. Sunrise over the Horseneck bridge floods the kitchen. Sunset with sailboats from the front.
Two structures on the property: the main house, which is yours, and the boathouse, which is the family's. Guest parking is on the left side of the driveway. The backyard extends to the river. Plenty of room.
The dock is active all summer. You're not renting from strangers. You're spending the summer at a place that's been lived in for generations. That's not a caveat. That's the experience.
Directly on the water at Westport Point with views of both branches of the Westport River. Sunrise and sunset from the house.
Swim off the dock, climb the ladder, dry off in the sun. Kayaks, a one-person canoe, and a Sunfish sailboat are available for the river and harbor. Just ask so we can get you set up. Full water safety details in the guest guide.
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.
If you need anything, a restaurant recommendation, a stuck lock, or help getting set up on the water, someone is always close.
Summer 2026: select weeks available. Check dates on Airbnb →
★★★★★
“This isn't a typical Airbnb. You feel like you're staying at a friend's family home on the water.”
Guest review
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. The sound of the water, the glow of the coals, and nowhere you need to be.
Our grandfather served in the State House for 24 years. Our father practiced law for forty years down the road in Fall River. We grew up catching crabs off this dock and watching lobster boats come in at sunset.
This house has been in the family for generations. When you stay here, you're part of that for a week. If you need anything, someone is always close.
See you this summer.
— The Long Family
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 or just listen from the porch.
Walking Distance
Walk to the oyster bar at Westport Sea Farms, the town dock, and the fishing pier. 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
State beach with miles of sand and strong surf. Walk west past the crowds and it opens up. About a 10-minute drive. More about Horseneck.
Nine Stories. Four Centuries. One Address.
Whaling ports, privateers, founding families, and the hurricane that changed everything. Explore the history below ↓
Summer 2026: select weeks available. Check dates on Airbnb →
★★★★★
“The location is unbeatable. We kayaked every morning and watched the sunset from the dock every night.”
Guest review
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.
Explore Westport's History
◎Nine clues hidden across nine pages. Find them all.
★★★★★
“We've stayed at dozens of rentals. This is the one we keep coming back to.”
Guest review
Summer Availability
Summer 2026 at Westport Point. Select your dates.
Been here before? Reach out directly for availability.
Guest Stories
Our first guest videos are coming this summer. Had a great stay? Send us your favorite moment.
FAQ
About a 10-minute drive. One of the best beaches on the South Coast of Massachusetts.
Yes. Dock space is available at $5 per foot per night. Kayaks, a one-person canoe, and a Sunfish sailboat are available on request at no additional charge. Ask ahead so we can get you set up.
3 bedrooms, 2 baths, updated kitchen with gas stove, views of both branches of the Westport River. The backyard extends to the river. The main house is yours. The boathouse on the property is the family's private space. Guest parking is on the left side of the driveway.
No, pets are not permitted at the property.
Check-in is at 3:00 PM. Check-out is at 11:00 AM. These times are firm. Cleaners are scheduled around turnovers and there is no flexibility. Full details provided after booking through Airbnb.
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.
The house is fully stocked: linens, towels, kitchen with gas stove, coffee maker, large lobster pot, outdoor grill with propane, kayaks, one-person canoe, Sunfish sailboat, life jackets, floats, fire pit, and beach chairs. Bring beach towels (for the beach, not the house), sunscreen, bug spray, a cooler, groceries (Lees Market is a 5-minute drive), and cash for lobster off the boats.
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. Weekly rates vary by season. Check Airbnb for current pricing and availability.
Good Neighbors
We take being part of this community seriously. This is not a party house. Quiet after 10 PM. Maximum 6 guests. Exterior cameras for safety. A family member is always minutes away.
This Summer
Reserve your dates at Westport Point. Once a week is booked, it's gone until next year.
Interested in summer 2027? Leave your name and email and we'll reach out when dates open.
Book Your Stay
Scan the QR code to view the listing and book your summer at 2042 Main Road, Westport Point, MA 02791.
Where You're Staying
2042 Main Road sits in the Westport Point Historic District, a designated historic district. 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.
The property came to the Longs through the Gifford family. Lafayette Gifford lived in this house. His father Albert kept a whaling log aboard the bark President out of Westport Harbor in 1849. The family's roots on this coast trace back further still, through the Coffins of Nantucket, the Folgers, and the founding families who built the whaling industry from these harbors. Four generations of Longs have gathered here.
A grandfather served 24 years as a Massachusetts State Representative. A letter from Senator John F. Kennedy dated November 1956, congratulating Representative Long on his first election and signed “Jack,” sits in the family archive. A 1966 note from Senator Edward M. Kennedy, who crossed out the typed greeting and wrote “John” by hand.
This isn't an investment property. It's a home 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.
Senator Kennedy, before he became the 35th President.
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 at Westport Sea Farms. 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 with families, couples, and dogs. Walk up the street to the old graveyard. Walk down to the docks and watch the light change over the harbor. Rolling, unhurried, gentle. The kind of quiet that makes you slow down without trying.
