| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Ivy Cottage
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| Name: Ivy Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1500/mo+ util winter* |
| East Gloucester. This delightful two bedroom English country-style cottage on an estate setting in has high ceilings, an oversized fireplace, a large and private yard with flower gardens, and lots of light.
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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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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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Stone Mansion
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| Name: Stone Mansion | Bedrooms: 10 | Bathrooms: 6.5 | SleepsMaximum: 18 | $6500/week contact realtor* |
| Go back in time to the Civil War era when Brig. General Greely Curtis came to Manchester by the Sea to build his mansion on a high bluff overlooking the Atlantic, with the Boston skyline and the Cape Cod shore visible in the distance.
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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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Rockport Village House
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| Name: Rockport Village House | Bedrooms: 3 | Bathrooms: 2.5 | SleepsMaximum: 8 | $1800/wk summer; $1200/week winter* |
| This immaculate and charming village gem offers versatility, style and convenience. A short walk to all that Rockport has to offer this 3 bedroom/ 2.5 bath home has quaint historic details, yet offers all modern conveniences and comforts with newly remode
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Eastern Point Ocean Vista
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| Name: Eastern Point Ocean Vista | Bedrooms: 5 | Bathrooms: 3 | SleepsMaximum: 10 | $5000/wk summer (Friday)* |
| New listing-Pool! Air conditioning! Located on Gloucester's prestigious Eastern Point, Eastern Point Ocean Vista offers views, privacy and passes to beautiful Brace Cove, a sandy beach in walking distance of the house. 5 bedrooms, 3 full baths...
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Wingaersheek Summertime
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| Name: Wingaersheek Summertime | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $3500/wk* |
| Wingaersheek Beach! This classic 50's beach house is just 75 yards to the sands of Wingaersheek's private beach. It has three bedrooms, one bath, beach shower and sleeps 6. Open concept living room with fireplace, dining room and kitchen.
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Changing Tides
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| Name: Changing Tides | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 5 | $1200/month + winter; $1900/week summer* |
| Situated on the shores of the tidal Mill River on a shaded lot of nearly one acre in Gloucester's watery Riverview district, this newly renovated property has a private dock and float. Swim, fish, or row in the dinghy left for your use.
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Edgemoor
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| Name: Edgemoor | Bedrooms: 4 | Bathrooms: 2.5 | SleepsMaximum: 7 | $2000-3000/wk summer* |
| Situated on a rocky shore, right on the Atlantic Ocean, this delightful, comfortable cottage on Gloucester's salty Brier Neck has a large yard leading down to the water. It commands excellent views of the Atlantic Ocean and Salt Island.
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