| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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SeaCrest Estate
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| Name: SeaCrest Estate | Bedrooms: 8 | Bathrooms: 7.5 | SleepsMaximum: 14 | please inquire* |
| This spectacular 4.2 acre estate on Manchester-by-the Sea's lovely Smiths Point offers the ultimate in oceanfront luxury and the perfect surroundings for your wedding or special event.
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Golden Sands
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| Name: Golden Sands | Bedrooms: 7 | Bathrooms: 3.5 | SleepsMaximum: 12 | $4000/wk summer* |
| Golden Sands is the quintessential turn of the century Gloucester "cottage." With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave!
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Wonson Cove Front
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| Name: Wonson Cove Front | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 5 | $1800/wk sum; $1500/mo+ winter* |
| From the shaded porch of this newly renovated property, you can enjoy your al fresco meals with the shores of Wonson's Cove just beyond. Newly polished hardwood floors and open floor plan give this a light and sunfilled feeling. The living room has a firep
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Ingomar at Rockaway Condominiums
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| Name: Ingomar at Rockaway Condominiums | Bedrooms: 3 | Bathrooms: 3.5 | SleepsMaximum: 4 | $25K/month of July* |
| Delightful free standing home on the grounds of the Rockaway Condominium complex. Exceptional views of Gloucester Harbor and Ten Pound Island.
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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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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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Cleveland Place Condo
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| Name: Cleveland Place Condo | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 2 | $950/mo + util.* |
| This immaculate one bedroom condominium is on the second floor of the complex. Located on a quiet dead end street, the unit has gleaming hardwood throughout a granite kitchen with an island and stainless appliances.
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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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Cottage on the Lane
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| Name: Cottage on the Lane | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | call for off season rates $2500/wk sum* |
| Leave your car in the driveway of this newly renovated and completely refurbished oceanview home and enjoy Cape Ann. Wander the quaint lanes of Rockport and browse at its many art galleries and boutiques on famed Bearskin Neck.
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Lily Pond Farm
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| Name: Lily Pond Farm | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $1500/mo+ win OR $1800/mo yr $1800/wk* |
| This lovelythree bedroom/ two bath victorian brings you back to the era when life was more serene and relaxed. Set in an idyllic and private area with woods on two sides and overlooking a glimmering pond forget it is the twenty first century!
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