Aerial view of a sailboat off the Cape Ann coast in Massachusetts

Cape Ann's boutique rental manager

We care for your home as if it were our own.

“By keeping our portfolio intentionally small, we provide hands-on care, maximize your revenue, and ensure every guest experience is five-star worthy.”
Allie O'Brien, Owner

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By the numbers

0.00★

Average guest rating

Excellence in hosting.

We devote our full energy to the guest experience, operating under the belief that our most valuable assets are our glowing five-star reviews.

Did you know?

After location and price, guest reviews are the third most important factor in booking decisions.

From our guests

Beautiful stays.
Lasting impressions.

The Neck waterfront boathouse overlooking Gloucester Harbor — The Neck · Gloucester

Wonderful location with beautiful scenic views.Immaculate with gorgeous nautical decor. Two beautiful decks to enjoy. Perfect family spot.

The reviews behind the number.

“Great place, unbelievable host. Beyond accommodating. 100 percent rent from her again.”

Alexis A. · Stay at Smith Cove

“Allie was great. The place was beautiful, the attention to details was amazing. Honestly covered anything you needed and more.”

Jenny B. · Stay at The Neck

“Beautiful, cozy, clean, private. It's my home away from home in Gloucester.”

Mike G. · Stay at Niles Beach

“Wonderful location with beautiful scenic views. Immaculate with gorgeous nautical decor. Two beautiful decks to enjoy. Perfect family spot.”

Al A. · Stay at The Neck

“Allie was responsive and welcoming. The home was beautiful, spacious, and filled with natural light. It was clean and had everything we needed. Would book again.”

Marisa M. · Stay at Beverly Shops

“I thought it was beautiful online, but once we walked in the home smelled good and was so clean and so beautiful and comfortable. We hated to leave.”

Melinda S. · Stay at The Neck

“Allie was a pleasure to work with. Very responsive to all messages.”

Kelly H. · Stay at Niles Beach

“We loved our stay. The place is beautiful. Allie was incredibly responsive. The house was outfitted perfectly for us.”

Meghan M. · Stay at Good Harbor Beach

“We are looking forward to our next stay with Allie.”

Bradley S. · Stay at Beverly Shops

“This is a gorgeous home. Felt very cozy and comfortable. Allie was a wonderful and communicative host. I would definitely stay here again.”

Amoy M. · Stay at Little River

“What a wonderful hidden gem. A memorable stay. Allie was super responsive. We had a delightful time.”

Deborah M. · Stay at Rocky Neck

Aerial view of a Cape Ann harbor on the Massachusetts coast

Our positioning

Boutique.

A small portfolio, held to a standard we can maintain.

Local.

We live on Cape Ann. We know this coast in every season.

Expertly Managed.

Hospitality-driven. Institutionally disciplined.

Where we work

Cape Ann, done right.

10 min

from every home

85 Eastern Ave

Gloucester HQ

Visit our HQ

Featured stays · Stay Cape Ann

Where guests stay.

Stay Cape Ann is our direct booking site for vacation rentals on the coast. Lower fees for guests, higher earnings for the homeowners we work with. Built so the people who live here, host here, and stay here keep more of what they spend.

Gloucester