Cape Ann,
feel at home.
Vacation rentals looked after by neighbors.
Picked by hand. Looked after by neighbors.
We live here.
You should too,
for a week.
Stay Cape Ann is owned and run by Rising Tide, a small Gloucester team. We live here year round, and we look after these homes through the off season so they're ready the day you walk in.
Every home is one we know personally, and one we'd send our family to for a week.
Notes from the coast.
Mid-October on Cape Ann: Peak Light, Thinning Crowds
The leaves inland are turning hard this week, the harbor is cold and clear, and the kitchen at your favorite spot is finally not slammed. This is the week to come.
Late September on Cape Ann: The Best Water Week
The crowds are gone and the ocean is still warm from August. This is the week we've been waiting for all summer.
Mid-September on Cape Ann: The Coast Exhales
The Schooner Festival crowd has gone home and the water is still warm. This is the week the coast starts feeling like it belongs to us again.
Quick answers for first-timers.
Is booking direct cheaper than Airbnb or Vrbo?
Yes. Every Stay Cape Ann home is also on Airbnb and Vrbo, where platform fees add roughly 14 to 20 percent to the guest's total. Booking direct at staycapeann.com skips those fees and gets the guest our best available rate plus direct access to our Gloucester-based team.
When is the best time to visit Cape Ann?
Mid-June through early October is the heart of the season, with warm ocean temperatures, open beaches, and headline events like Saint Peter's Fiesta in late June and the Gloucester Schooner Festival over Labor Day weekend. Spring and autumn are quieter with cooler weather and dramatic coastal light. A handful of homes remain open year-round for winter stays.
How far is Cape Ann from Boston?
About 35 miles, which typically translates to 35 to 50 minutes by car via Route 128, depending on traffic. Boston Logan Airport is roughly 40 minutes south, and the MBTA commuter rail runs to Rockport and Gloucester.
What is there to do on Cape Ann?
Cape Ann's signature experiences include Good Harbor Beach, Wingaersheek Beach, and Old Garden Beach; the Rocky Neck art colony; downtown Rockport's Bearskin Neck and Motif No. 1; Hammond Castle, the Cape Ann Museum, and Maritime Gloucester; and day hikes at Halibut Point State Park and Ravenswood Park. The Weekly covers rotating picks for restaurants, shops, and seasonal events.