Plum Point · Chesapeake Bay
A handful of waterfront cottages where the sunsets are loud and the mornings are yours.
Stay. Relax. Repeat.
Waterfront cottages
A handful of homes, each cleaned and styled in-house, never a faceless rental.
Average guest rating
Couples and families return season after season for the quiet and the views.
Local hosts on call
We're minutes away the whole stay, so everything stays effortless.
Featured cottage
Cottage #15
Our most-loved cottage: an open kitchen that spills onto the firepit, the bay just beyond the grass, and evenings that stretch long past sunset.
Our top
cottages
Six waterfront stays at Plum Point: cleaned, styled, and managed in-house for a seamless escape.
Browse by: Pet-friendly · Family · Free kayaks · For couples
Explore
the bay
Plum Point sits on Maryland's western shore, quiet, unhurried, and a short drive from everything good on the Chesapeake.
Full area guide
The story of Plum Point
15 million years underfoot.
The cliffs along this shore are the floor of an ancient sea, and megalodon teeth still wash out of them after a good storm. Before the cottages there was a steamboat wharf three quarters of a mile long, and before that, a 1673 map with our name on it. It's a good story.
Welcome to Plum Point Cottages
Where pure views meet peace of mind.
Your getaway should be as effortless as it is unforgettable. Relax on the shore, unwind in a cozy cottage, or explore the beauty of the Chesapeake and beyond. You've come to the right place.
Every cottage is designed to deliver relaxation, enjoyment and “Pure Views” to your eyes and soul. We take care of the details so you can focus on making memories.
And the tradition runs deep: the colony here dates to about 1940, and families have been trading the city for this shoreline every summer since.
Explore the cottages
Guest reviews · 5.00 average
“The bay was steps away and the sunsets were unreal. We never wanted to leave.”
Maria & James · Cottage #14
“Booking was seamless and the firepit nights were the highlight of our trip.”
The Okafor family · #15
“Pet-friendly, quiet, and beautiful. We've already booked our next stay.”
Dana & Will · #20
“Every detail was thought through. It felt like a home, not a rental.”
Priya & Sam · #3
Your next escape
is on the bay.
Check availability for your dates and let us handle the rest.
Check availability