Hi, I’m Allie O’Brien.
Stay Collections started because I couldn't find what I was looking for: a small, trusted collection of genuinely special homes on Cape Ann, where you could book directly, skip the fees, and actually talk to someone who knew the house, the beach, and the best place to grab chowder on a Tuesday night.
So I built it.
What We Actually Believe
Cape Ann is different. Gloucester isn't the Vineyard. Rockport isn't the Cape. It's grittier, more real, and — if you know where to stay — more beautiful than either of them. Every home in Stay Collections is one I've personally vetted, because I live here and I care what you think when you wake up and walk out the door.
No middleman.
Booking direct means better prices, real communication, and no Airbnb service fee eating 15% of your trip budget.
Local knowledge.
If you’re wondering which beach has the best parking at 9am in July, or which lobster rolls are worth it, I’ve got you covered.
Cape Ann Is the Best-Kept Secret on the East Coast
Thirty minutes north of Boston, Cape Ann sits at the edge of the Atlantic — fishing boats in the harbor, granite ledges dropping into the sea, beaches that make you forget you're in Massachusetts. Gloucester is America's oldest seaport. Rockport's art colony has been drawing painters since the 1800s. And somehow, neither of them ever gets as crowded as they deserve to be.
That's the secret. And staying here, really staying, in a home that belongs to this place, can make all the difference.
