Cape Ann’s
Best Stays.
No Markup. No Middleman
Handpicked homes in Gloucester, Rockport & Beverly.
Featured properties
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![Aerial view of a residential neighborhood with multiple houses, trees, and greenery, under a clear blue sky.]()
Good Harbor
Steps from Gloucester’s most beloved beach, Good Harbor is the perfect blend of relaxation and adventure. Wake up to ocean breezes, sip coffee on the deck, and spend your days sinking your toes into soft white sand or exploring nearby coastal trails. Whether you're catching the sunrise over Salt Island or unwinding after a day in town, this seaside retreat offers the ultimate New England escape.
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![A waterfront house with large windows and a wooden deck, situated on rocks and water, with neighboring houses on a hillside surrounded by trees.]()
Rocky Neck
Set in the heart of America’s oldest art colony, Rocky Neck is a vibrant coastal retreat where creativity meets seaside charm. Wake up to harbor views, sip coffee on the deck, and spend your days wandering through galleries, waterfront cafés, and boutique shops. Whether you're soaking in the local culture or relaxing by the water, this artistic enclave offers the ultimate New England escape.
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![A view of a lake with a wooden dock extending into the water, surrounded by green grass and trees under a blue sky with fluffy clouds, and part of a house on the left side of the image.]()
Little River
Nestled along the peaceful banks of Little River, this waterfront retreat is a perfect balance of nature and relaxation. Wake up to the sound of the tide, sip coffee on the dock, and spend your days kayaking through winding waterways or lounging by the water’s edge. Whether you're exploring nearby trails or simply soaking in the river views, this secluded haven offers the ultimate New England escape.
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![Bright living room with white walls, a white sofa with blue and beige pillows, a white coffee table with a vase of white tulips, framed bird artwork on the wall, a wicker chair with a cushion, a sliding glass door, and skylights in a vaulted ceiling.]()
Niles Beach
Tucked away along Gloucester’s scenic coastline, Niles Beach is a serene retreat with sweeping harbor views. Wake up to the gentle sound of waves, sip coffee on the deck, and spend your days strolling the quiet shoreline or paddleboarding on calm waters. Whether you're watching the sailboats drift by or exploring downtown’s vibrant scene, this hidden gem offers the ultimate New England escape.
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![A two-story mint green house with black shutters and a white picket fence, accompanied by a small matching garage and landscaping with trees and shrubs.]()
Beverly Shops
In the heart of North Beverly, this property blends everyday convenience with relaxed comfort. Start your mornings with coffee on the deck, spend the day exploring local shops, dining, and unwind at home in bright, welcoming spaces made for gathering. Whether you're here for work, family time, or a weekend reset, this centrally located retreat offers an easy, well-connected North Shore stay.
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![Living room with large windows revealing a view of a marina and boats, featuring a brick and wood interior with a fireplace and a sliding glass door leading to a balcony.]()
Smith Cove
Perched above Gloucester’s scenic Smith Cove, this rare waterfront retreat offers front-row harbor views and effortless coastal charm. Wake up to boats gliding by, sip coffee on the expansive deck, and spend your days immersed in the beauty of Rocky Neck. With soaring ceilings, sun-filled spaces, and sweeping water views, this one-of-a-kind escape captures the essence of life on the harbor.
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![A two-story modern house with gray vertical siding, dark window frames, and a wooden front door. The house is surrounded by lush greenery and blooming pink flowers, with a brick walkway leading to the entrance.]()
Old Garden Beach
Tucked between downtown Rockport and Old Garden Beach, this architect-designed retreat offers the perfect balance of coastal access and quiet privacy. Wake up to morning light, sip coffee on the deck, and stroll to the beach or into town for shops and dining. With clean modern design, open living spaces, and thoughtful details throughout, this elevated escape makes it easy to settle in and unwind.
“A memorable vacation isn’t just about where you stay—it’s about the care and hospitality that make you feel at home.”
-Allie O’Brien
Guest Experience Lead | Stay Collections
Hundreds of guest stays. Hundreds of 5-star reviews.
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![A smiling woman with curly hair wearing glasses, hoop earrings, and layered necklaces, indoors with a blurred background.]()
"We had a wonderful stay. The house was very clean, comfortable and exactly as described in the listing. It had everything we needed!"
★★★★★
Swetha | Providence, RI
Stay at Niles Beach
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![A man with curly dark hair, glasses, and a beard, wearing a dark green sweater and white shirt, looking to the side with a slight smile in an indoor setting with a plant in the background.]()
"...this booking hit all of the boxes. Warm, intimate, fun... beautiful location. It was just beyond what we could have expected."
★★★★★
Doug | Dublin, OH
Stay at Lighthouse Beach
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![A woman with shoulder-length black hair smiling in front of green foliage.]()
“The home is lovely and set-up for every need you have. Allie was a pleasure to work with. The location and views are beautiful."
★★★★★
Barbara | Durham, NC
Stay at Good Harbor
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![A young woman with wavy brown hair wearing a red turtleneck sweater, smiling broadly with red lipstick, outdoors.]()
"We spent a lovely extended weekend at Allie's place. The house was spotless, the furnishings are casual chic, and the neighborhood is full of fun restaurants."
★★★★★
Mary Ann | Potomac, MD
Stay at Black Rock Harbor
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![A woman with brown hair and bangs smiling outdoors, wearing a black shirt and a colorful embroidered jacket with red, yellow, and black patterns.]()
"We had a wonderful time and enjoyed the spaciousness the house offers to a big group. I thought the house was one of the cleanest I've stayed in and had everything we needed."
★★★★★
Andrea | Wilmington, MA
Stay at Good Harbor
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![A man with dark hair and a beard, wearing a light blue shirt, standing on a beach with boats in the water and houses in the background.]()
"The house itself is beautifully designed, very clean and comfortable, and had everything we needed. Allie always responded quickly to the couple of questions we had, and was very friendly and helpful."
★★★★★
Dan | Los Angeles, CA
Stay at Lighthouse Beach
