| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Annisquam Lookout
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| Name: Annisquam Lookout | Bedrooms: 4 | Bathrooms: 1 | SleepsMaximum: 7 | $1200/month plus utilities* |
| This is a delightful find tucked into a lovely corner of Gloucester's Annisquam district. The bright and airy ground floor has lots of light and great views of Ipswich Bay.
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Windward
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| Name: Windward | Bedrooms: 4 | Bathrooms: 3 | SleepsMaximum: 8 | $7500/wk summer* |
| Beachfront! The white sands of Long Beach await you just steps from this spectacular four bedroom three bath contemporary treasure! Boasting expansive views of the world famous Twin Lighthouses of Rockport and beyond to the open Atlantic...
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Good Harbor Getaway
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| Name: Good Harbor Getaway | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 4 | $650/wk summer* |
| This simple but private apartment is located on the ground floor of a summer home in Gloucester's prestigious Briar Neck neighborhood. From its shaded patio, you look out to its lovely perennial garden.
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Brightside Cottage
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| Name: Brightside Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 6 | $1000/month+ winter* |
| Only a half-mile (an easy walk) to the pristine white sands of Gloucester's Good Harbor Beach, this immaculate 2 bedroom ranch house comfortably sleeps six. Located in a quiet neighborhood the cottage is the perfect place to wind down after a long day at
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Beacon Hill
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| Name: Beacon Hill | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1200/mo+ YR* |
| YEAR ROUND: A charming little house set back from the street in downtown Gloucester offers a short walk to the train station, city hall, library, restaurants, harbor and so much more.
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Eden Lights
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| Name: Eden Lights | Bedrooms: 7 | Bathrooms: 2.5 | SleepsMaximum: 14 | $6000/wk summer* |
| Oceanfront! Welcome to this inviting renovated property built a century ago at the edge of Rockport's rugged Atlantic coastline. Once you enter its spacious living room with fireplace and walk out onto its wraparound porch, you will never want to leave!
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Harbor Breezes
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| Name: Harbor Breezes | Bedrooms: 2 | Bathrooms: 0 | SleepsMaximum: 4 | $1400/mo includes heat* |
| Waterfront, Rockport Year round! rent INCLUDES HEAT. This large two bedroom unit is on the third floor of a waterfront building in the heart of quaint Rockport. Combination living/dining rooms have lovely views of Front Beach and Sandy Bay beyond.
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Emerson Cottage
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| Name: Emerson Cottage | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $3500/wk July, $3900/wk August* |
| This charming 3 bedroom/1.5 bath home in the Pigeon Cove section of Rockport has glorious views of Sandy Bay. Sit on the spacious wraparound porch, in the hot tub large enough for six, or splash in the freshwater pool next door at the Inn...
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Wessex Cottage
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| Name: Wessex Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1350/month plus utilities* |
| This enchanting 2 bedroom/1 bath, single level cape is a five minute walk from 2 beautiful beaches in Rockport's charming South End. There are ocean views, and a large lot with plenty of Cape Ann's signature granite outcroppings.
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Annie's Place
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| Name: Annie's Place | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | $1200/week summer* |
| This delightful home in Gloucester's picturesque Bay View district and is full of sun and warmth. A five minute walk brings you to the neighborhood beach of Plum Cove which along with great swimming offers a good chance of a tiny hermit crab sighting.
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