| 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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Post & Beam
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| Name: Post & Beam | Bedrooms: 3 | Bathrooms: 3 | SleepsMaximum: 8 | $2750/wk summer* |
| This very special, private & lovely, owner-built, post & beam house is centrally located in historic and quaint downtown Rockport, offering a surprisingly spacious living area for your ideal vacation getaway!
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Monarch Glen
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| Name: Monarch Glen | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $1495/mo+ winter; $2000/wk summer* |
| Less than half a mile from Gloucester's sandy Good Harbor Beach, this delightful property is nestled on a quiet half acre wooded lot, making it a perfect respite on a hot summer day!
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Garden Ledges
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| Name: Garden Ledges | Bedrooms: 2 | Bathrooms: 2 | SleepsMaximum: 3 | $1650 plus Year Round* |
| Just steps from Rockport's Cape Hedge Beach, this newly renovated two bedroom two bath home awaits a year round tenant. It's oversized sunny living room with brick fireplace opens onto a large deck with ocean views...
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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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Red Roof
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| Name: Red Roof | Bedrooms: 5 | Bathrooms: 2.75 | SleepsMaximum: 10 | Speak to your realtor* |
| A.Piatt Andrew Jr.(1873-1936) visionary, statesman, Harvard Economist, officer of WWI as well as architect and designer of the waterfront gem he called “Red Roof” on Gloucester’s Eastern Point. The visitor is offered a glimpse of his intensity of vision...
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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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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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Sunny Beach
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| Name: Sunny Beach | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | $1500/mo+ winter $2000/week summer* |
| This light-filled and airy home is on the marsh with expansive views looking out towards Good Harbor Beach, one of Gloucester's finest sandy beaches which is just a few minutes walk away.
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Good Harbor Hideaway
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| Name: Good Harbor Hideaway | Bedrooms: 4 | Bathrooms: 2.5 | SleepsMaximum: 6 | $1800/mo+ winter* |
| This delightful newer Gloucester home is just a stone's throw to Good Harbor Beach. Set on a quiet residential lane, it offers ocean views across a scenic marsh.
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