| 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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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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Sunny Ledges
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| Name: Sunny Ledges | Bedrooms: 4 | Bathrooms: 3 | SleepsMaximum: 6 | $2000 mo+ winter* |
| Enjoy lovely ocean views from this sunny, contemporary four bedroom/ 3 bath home built in 2000. The house is on a quiet cul de sac surrounded by lovely perennial beds which can be enjoyed from any of the 4 decks. Available as an off season rental October-
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The Galley
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| Name: The Galley | Bedrooms: 0 | Bathrooms: 1 | SleepsMaximum: 2 | $1000/mo+ winter; $950/week summer* |
| Waterfront! Adorable studio cottage right on Smith Cove. Everything you need in one room: a queen bed, a rocking chair sofa, fireplace, stack washer and dryer, new galley kitchen, full bath (tub with shower) and most of all an exquisite verandah with co
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Bottom's Up
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| Name: Bottom's Up | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1000/wk summer* |
| "Bottom’s Up!” This two bedroom one bath hidden gem is located in the heart of the historic and scenic North Shore in Beverly. Nestled in a cul de sac, it’s a little off the beaten path, while still allowing easy access to Gloucester, Rockport, Manchester
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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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Spindrift
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| Name: Spindrift | Bedrooms: 4.5 | Bathrooms: 2.75 | SleepsMaximum: 10 | $3750/wk or $2500/mo includes util* |
| Direct waterfront, Rockport South End & central air! A spindrift is windblown seaspray which is a regular sighting at this lovely home that is as close to the Atlantic as the ocean will allow...
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Seven Knots
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| Name: Seven Knots | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $2000/mo includes util or $32K for summe* |
| Standing in the living room of this cottage is just as close to be floating as one can be without a boat! Spectacular views from every corner of the house.
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Eastern Point Tower
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| Name: Eastern Point Tower | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 2 | $1500/mo+ YR* |
| Located in a private wooded area near the famous Eastern Point Lighthouse in Gloucester, this one of a kind, 3 level, 1 bedroom house is the perfect peaceful, romantic retreat. The top floor offers views of the ocean.
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Upper House
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| Name: Upper House | Bedrooms: 2 | Bathrooms: 2 | SleepsMaximum: 3 | $1600/mo plus util* |
| This brand new waterfront home, located on a private family compound in Gloucester's Bay View district, was built to the highest standard. it boasts exceptional views of Ipswich Bay, with its glorious sunsets, from both levels.
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