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Stay at Little River

Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Waterfront setting on peaceful Little River with private dock access ✓ Sleeps 7 across 4 bedrooms: king, queen, and 3 twins ✓ Fully renovated with bright interiors, central AC, and modern comforts ✓ Outdoor patio with dining, lounge seating, grill, and river views ✓ Minutes to Stage Fort Park, downtown Gloucester, beaches, and trails See more photos, video tours, and local recommendations on IG

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Blue Magnolia

High in the treetops, this spacious apartment is only two blocks from the Atlantic Ocean! You'll enjoy 1400+ square feet with beautiful hardwood floors, an all-new kitchen, and your choice of two comfortable bedrooms -- one king and one queen. With a sleeper sofa, the apartment can sleep six total. This is a 2-flight walkup with private entrance, plus access to a large patio and well-established plantings including roses & a grassy yard. Offstreet parking in back if needed, thru driveway gates.

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

The Artist Suite by Toi Moi

Welcome to Toi Moi's latest addition to AirBnb. This art-filled and chic suite with its own entrance and parking area blends influences from the Wabi-sabi philosophy, minimalist design, and old world treasures collected from our trips to create a unique aesthetic experience unavailable anywhere else on the North Shore. The Artist Suite is attached to our private home deep in the woods, creating a space for the solo traveler or romantic couple looking for serenity and inspiration.

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

Parsons at Stage Fort

Our historic home is steps from so many things that Gloucester has to offer. We are located across the street from the Stage Fort park, which includes Cressy and Half Moon beaches, tennis courts, large open green spaces, and beautiful scenic views. Walk along the boulevard lined with flowers! Stop at the cut bridge to see boats going out to sea and the famous fisherman statue. Continue downtown to enjoy one of Gloucester’s many gourmet restaurants. So much to do in Cape Ann!

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

William Haskell House First Period Colonial Home

A First Period Colonial American experience in beautiful Gloucester, Massachusetts! As you step through the threshold of this sensitively restored 1680 residence, you are transported to an earlier time—immersed in the history of the home and the area. This listing reserves all four rooms in the house: Parlor Chamber, North Ell, the Spinning Room and The Gambrell Bedroom. As well as access to the kitchen and lounge area that has a television.

Ipswich Waterfront Getaway

Welcome to Eagle Hill House in beautiful Ipswich, perched on a waterfront bluff, with amazing views of Plum Island Sound. Watch herons wade and osprey dive for fish as you relax. Private stairs lead down to a rocky beach. It’s the perfect place to bring a kayak or SUP board. You have exclusive use of lower level walkout apartment with private entrance.

New Design - Walk to DNTN, Beauport, Beach, Train

🌊 The Crows Nest! | Coastal Balcony Retreat • Walk to Beach & Downtown Gloucester Welcome to The Crows Nest! — your elevated seaside escape in the heart of beautiful Gloucester, Massachusetts. Perched above it all, this bright and inviting retreat offers the perfect blend of coastal charm, walkability, and modern comfort.