Cape Ann, MA
60 properties available
Experience river life at its best along the banks of Mill River when you stay at this spectacular waterfront rental home with exquisite water views, a large back yard, and a private tidal dock for swimming and kayaking.River Watch is a charming antique home sun-filled with natural light, and beautiful hardwood floors throughout. From the front door
New for 2026! Stroll to Long Beach or Good Harbor Beach, or simply relax on the large deck. Nestled between the two beaches, it's just a few hundred yards from Long Beach, with Dairy Maid, serving ice cream and sandwiches, just around the corner.This inviting coastal home offers an ideal blend of comfort, space, and proximity to the area’s most bel
Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage Hill is the perfect vacation destination. Walk to Long Beach (about a 5 minute walk), or take a short drive to Good Harbor Beach. Sage Hill is well appointed, with a roomy eat-in kitchen, a breakfast bar and an adjoining deck w
Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect vacation spot. The bright and airy ground floor has many windows, letting in lots of natural light. Upstairs, there are 3 bedrooms and a full bath with clawfoot tub and shower. AC units are in each of the bedrooms and the
The View is a quintessential one-story New England cottage with stunning views of Pigeon Cove. This rental home has two bedrooms, an open plan living/dining room with a wall of windows looking out towards the ocean, a modern kitchen, and a 3-season glassed-in porch offering an extra sleeping space, and a deck. Air conditioning will keep you cool th
Located in Gloucester's Harbortown neighborhood, the name Harbortown Hideaway perfectly suits this vacation rental. A charming historic home, newly renovated features beautiful architectural details and offers visitors the comforts of contemporary living. You'll love the harbor views from both inside the house and from the deck/porch areas. Enjoy t
Sitting high above Rocky Neck, Painter’s Perch offers stunning views of the Neck and picturesque Smith Cove. This charming 2-bedroom, 1.5-bathroom retreat is the perfect getaway for art lovers, outdoor enthusiasts, or anyone seeking tranquility near the heart of Gloucester's vibrant arts district.The home boasts an array of outdoor spaces to enjoy
Please note that The Gallery has a one month (31 night) minimum rental period.Welcome to The Gallery, a stunning waterfront multi-level property on Rocky Neck, America's oldest art colony. Located above a studio run by the Rocky Neck Art Association, this home puts you in the heart of the action. Enjoy views of Smith Cove and the Gloucester skyline
Welcome to Spyglass, a bright and breezy third-floor apartment offering water views and a peaceful perch in the quaint seaside village of Lanesville. This newly updated two-bedroom retreat features a remodeled kitchen and bathroom, and air conditioning throughout; everything you need for a relaxing Cape Ann escape.Enjoy a private entrance at the re
Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two-bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the primary bedroom have sliding doors that open onto a spacio
Escape to this charming 3-bedroom vacation home, nestled among the trees with ocean views. Step out onto the spacious deck complete with outdoor dining, a sectional sofa and umbrellas from where you can enjoy the tranquil surroundings and the ocean breeze.Just .2 miles from Long Beach, there is a public path and footbridge for easy beach access.Fir
Welcome to Dot’s Place, a bright and comfortable one-bedroom apartment in the heart of Rockport. Tucked away on a quiet lane, this freshly renovated space offers a peaceful retreat while keeping you close to everything—beaches, shops, restaurants, and the renowned Shalin Liu Performance Center.Designed for one or two guests, this charming apartment
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