The Guide to the Local Way of Life on Cape Ann & Boston’s North Shore

How to Sleep in a Stranger’s House Tonight

How to Sleep in a Stranger’s House Tonight


For centuries, Gloucester, Rockport, Essex, and Manchester-by-the-Sea have attracted a wide variety of visitors, from pleasure-seekers to pilgrims to artists.

Still, today’s visitors will note with some relief that quaint Cape Ann, for all its fairytale allure, has firmly entered the 21st century in at least one regard — we’ve heartily embraced the modern convenience that is Airbnb.

Founded in 2008, and now worth $1.7 billion, Airbnb, the ‘unicorn’ start-up that allows ordinary people to turn their guest bedrooms and summer homes into accommodations and an extra income stream, has finally found solid footing on Cape Ann.

Here, permanent residents and summer owners alike appreciate the ease of the platform for arranging rentals and short-term stays.

Meanwhile, the Airbnb system provides a stylish, budget-friendly option for would-be visitors that want to experience our community from their very own home base.

With that in mind, we’ve rounded up a few of our favorite local Airbnb options, all of which combine comfort, style, and undeniable Cape Ann charm and quirkiness.



If you’re seeking the seclusion of an island getaway in a wide-open bucolic setting, the Quarry Master’s House in the Lanesville section of Gloucester is ideal.

Set on an expansive lawn complete with ornamental garden beds and native granite outcroppings, this beautiful clapboard Colonial home boasts a rich history as part of the Cape Ann granite industry.

Gracious sweeping windows light the interior of the 4-bedroom house, whose wide-plank-floored rooms are furnished in almost Shaker-like simplicity, though very comfortably — a paean to Yankee sophistication.

Also: no extra charge for the outdoor shower, the piano, or the toasty wood stove, either.

Details: $402/night; to book, contact Johanna.



Searching for a spot to host an extended family vacation or a reunion with old friends? Look no further than this scenic, well-appointed estate in Essex.

A waterfront beach lodge overlooking the dramatic vista of salt marsh conservation land, Clamshell Landing is the ultimate in group vacation getaways.

The understated salt-swept exterior belies a spectacular space with every amenity on offer; this 30-acre vacation home is fully equipped with a tennis court, private gym, half-basketball court, and much more.

The sprawling estate sleeps fourteen across its expanse of cozy bedrooms, and is also fitted with ample communal living space, from the open plan sitting area to the wrap-around porch.

This is a must-book for anyone looking for an active, outdoorsy vacation with all of your favorite people.

Details: $1900/night; to book, contact Atlantic Vacation Homes.


The Forge, Gloucester


A quaint stone cottage nestled in the larger expanse of a Gloucester estate, the Forge is a private escape overlooking the natural beauty of Dogtown Commons in the town’s Lanesville neighborhood.

This historic 1930s bungalow is beautifully constructed from local stone, and combines rustic, rough-hewn charisma with stately history and abundant modern conveniences.

Outside, the pastoral facade of the stonework pairs with blue wooden accents and barn doors; inside, a lofted sleeping nook tucked under the eaves looks out over the expanse of the living area and kitchen.

The cozy space is ideal for a writer’s retreat or for a romantic couples’ getaway; it’s a charming pastoral escape for any season.

Details: $140/night; to book, contact Deborah.


Modern Cottage, Gloucester


This lovely clapboard cottage combines an urbane contemporary aesthetic with the secluded privacy of Gloucester’s Annisquam Village.

The 2-bedroom home is a modern update on traditional 19th century home, and perfectly marries an antiquarian sensibility with updated fixtures and zeitgeist-ready style.

Inside, the comfortable cottage features an open-plan kitchen and living space, flanked on the ground floor by a master bedroom and full bath. A lofted second bedroom tucked back behind discreet shelving looks out over exposed beams into the space below.

No matter the season, this is an ideal retreat for a family getaway, and in the summer, it comes with the added bonus of a private beach within walking distance.

Details: $299/night; to book, contact Lauren.


The Glenacre, Rockport


Cape Ann is teeming with culture, art, and ample opportunities for retail therapy, but that doesn’t mean that there’s any shortage of pastoral vistas.

The Glenacre is a prime example; this quiet country home is set back from the hustle and bustle with characteristic subdued romance.

The home, which sleeps four, is located in Rockport’s Pigeon Cove neighborhood, and boasts a calming solace of an interior framed by exposed beams, and furnished in plush white linens and gleaming granite.

Details: $200/night; to book, contact Lina.


Stucco Oceanside, Gloucester


A four-bedroom just minutes walking distance from Gloucester’s popular Good Harbor Beach, this beautiful home is ready to host you.

This gracious stucco home with vivid turquoise accents fits seamlessly into the quirky, creative neighborhood of the Rocky Neck Art Colony, and boasts a sophisticated, colorful interior to match.

Inside, the home features a large, gracious living area and sunroom perfect for relaxing with friends and family. The updated kitchen will be a major draw for home-cooks, and the two serene, stylish baths make for the perfect escape from quotidien chaos.

In summer, spring, and early fall, gardeners will appreciate the landscaped lawn and flourishing garden beds studded with native flowers.

Details: $450/night; to book, contact Patricia.


ArtHouse, Manchester-by-the-Sea


Creative types who yearn for a quiet artist’s retreat will love this pristine Victorian in Manchester.

Located steps from Manchester’s bustling downtown, this home combines easy access to commerce and culture with plenty of peace and quiet.

The four-bedroom is home is great for families and couples alike, and is finely decorated in the characteristic expressive style that gives ArtHouse its name and calling card.

Peppered with unique fixtures and unexpected works of art, this bastion of creative sensibilities is ideal for anyone looking to soak in the rich culture and history of Cape Ann’s art scene, and is conveniently located just steps from the community’s many galleries.

Details: $675/night; to book, contact Jeremy.


The Haskell House, Gloucester


Next time you’re feeling that Crucible/Scarlett Letter vibe, we’ve got the perfect place for you. You can experience the 1600s firsthand with a stay at West Gloucester’s renowned William Haskell House.

This exquisitely preserved historic home, one of the oldest in the area, was built in 1680 and, at nearly 340 years old, dates back to the earliest days of the American Colonial Period.

Today, a stay in this home combines traditional architecture, lovingly preserved, with the latest in modern amenities.

There are few spaces left that so authentically preserve historical details, from the many working, brick-lined fireplaces to the abundance of antique furniture on display — it’s a history buff’s dream.

Details: $600/night; to book, contact Pam.



A minimalist masterpiece, this quaint and cozy loft over Rockport’s Bearskin Neck is the ultimate seaside getaway.

Come for the enviable view out over Rockport Harbor and both Front and Back Beaches, stay for the serene comfort of this stylish apartment.

This space combines a taste for old New England aesthetics — think exposed brick and lots of wood detailing — with modern sophistication.

The first floor includes a pocket kitchen and comfortable living space, while the second-floor loft is a tidy sleeping nook with an unbeatable view.

Best of all, you’re just steps from top-notch dining and shopping on the Neck.

Details: $140/night; to book, contact Wendy.

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