| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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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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West Wind
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| Name: West Wind | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 9 | $3500/wk summer/ $2200/mo+ winter* |
| Overlooking the Ipswich Bay in Annisquam, this tastefully renovated ranch is comfortable and pretty with some of the best views on Cape Ann!
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Quarryman's Cottage
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| Name: Quarryman's Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 2 | $700/+ taw* |
| Exceptional views of Ipswich Bay and the Massachusetts and New Hampshire coastlines abound from this charming year-round quarryman's cottage in Gloucester's Bay View neighborhood.
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Long Beach House
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| Name: Long Beach House | Bedrooms: 5 | Bathrooms: 2.5 | SleepsMaximum: 10 | $2500/week* |
| This large, comfortable family home is just steps from the white sands of Long Beach--a perfect summer location! Although we don't brag about its view, the location is superb!
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Ipswich Bay House
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| Name: Ipswich Bay House | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 8 | $1900/month + winter* |
| This spacious, beautiful contemporary home (2500 sf) in an estate setting in Gloucester's coveted Annisquam district has private sandy beaches (shared by a lucky few), boating and a fresh water pond just outside the door.
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Bates Cottage
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| Name: Bates Cottage | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 5 | $9500 for summer season* |
| This utterly sweet cottage in Rockport's beautiful Folly Cove district gives you the feeling that you are residing in the year 1805. It is bright and sunny with access to a swimming cove and shared deck overlooking the water.
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Beach Stone Cottage
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| Name: Beach Stone Cottage | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $2000/month plus util $3500/wk summer* |
| Good Harbor Beach! Updated and comfortable with views this 3 bedroom/2 full bath home boasts a large modern kitchen, two spacious sitting rooms a private yard-all just feet off the white sands of Good Harbor Beach.
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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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The Hideout
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| Name: The Hideout | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 4 | $1150/week* |
| Bring your boat and swim from this immaculate cottage that makes you feel as if you are floating in a well appointed vessel not only because of the view, but also the ingenious use of space, with many built-ins and the overall innovative decor.
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Harborfront Condominium
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| Name: Harborfront Condominium | Bedrooms: 2 | Bathrooms: 1.5 | SleepsMaximum: 4 | SUMMER 2009 $1950/week* |
| Manchester waterviews! This aptly named 2 bedroom/1.5 bath condominium overlooks picturesque Manchester Harbor and is within steps of everything the village has to offer great restaurants, shops, galleries...
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