| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Brier Neck Lookout
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| Name: Brier Neck Lookout | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 8 | $3500/wk summer; $2200/wk Sept/Oct* |
| Views of the Atlantic Ocean abound from the deck of this recently remodeled cottage, perched on a bold granite outcropping at the highest point of Briar Neck. A short stroll will bring you to Good Harbor, one of Gloucester's finest sandy beaches.
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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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Bass Rocks
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| Name: Bass Rocks | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $1000/mo+ winter* |
| Tucked away behind the friendly owner's home, this attached East Gloucester cottage is a perfect retreat after a day of lounging on Good Harbor Beach, less than 1/4 mile away. Its separate driveway, perennial gardens and lawn provide shade and privacy.
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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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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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Windward
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| Name: Windward | Bedrooms: 4 | Bathrooms: 3 | SleepsMaximum: 8 | $7500/wk summer* |
| Beachfront! The white sands of Long Beach await you just steps from this spectacular four bedroom three bath contemporary treasure! Boasting expansive views of the world famous Twin Lighthouses of Rockport and beyond to the open Atlantic...
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Driftwood Back Bay at Niles Beach
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| Name: Driftwood Back Bay at Niles Beach | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 6 | $1200/month + util. winter* |
| Rent the property featured in the Globe summer spectacular! This brand new East Gloucester cottage is less than 100 steps to sandy Niles Beach. It offers a large living room with cathedral ceiling with door to deck, one bedroom, a loft and a full bath.
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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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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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Plum Cove
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| Name: Plum Cove | Bedrooms: 5 | Bathrooms: 3.5 | SleepsMaximum: 10 | $1800/mo+ winter $3000/wk summer* |
| This recently renovated colonial a short walk from Plum Cove beach has four bedrooms, 2.5 full baths AND a guest unit with bedroom, full bath, and sitting room with pullout sofa on the lower level. Large sun room overlooks grassy back yard adds to the cha
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