| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Via Benevento
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| Name: Via Benevento | Bedrooms: 2 | Bathrooms: 2.5 | SleepsMaximum: 4 | $2500/month plus util. year round* |
| FURNISHED YEAR ROUND RENTAL: Newly constructed 2 bedroom, 2.5 bath condominium in the historic West End of Main Street in downtown Gloucester...
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Captain's Cottage
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| Name: Captain's Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1,500* |
| This delightful pine-paneled cottage is located on a quiet Rockport lane just steps from Cape Hedge Beach. From its sun room/sleeping porch, you can enjoy views of the Atlantic or walk across the private footbridge to the beach.
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Upper Beach Walk
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| Name: Upper Beach Walk | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 3 | $1200/mo+ util. avail. winter only* |
| Winter! Steps away from the Good Harbor Beach foot bridge, this bright and sunny second floor three bedroom, one bath unit offers comfort and convenience.
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West Wind
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| Name: West Wind | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 9 | $3500/wk summer* |
| 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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Wiley's Way
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| Name: Wiley's Way | Bedrooms: 2 | Bathrooms: 1.5 | SleepsMaximum: 4 | $1600/week* |
| A charming cottage located in Gloucester's fabled artist colony of Rocky Neck, on a quiet side street. Two bedrooms and 1.5 baths. Enjoy the great room and the private and enclosed outside area with seating for four and a grill.
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Wonson Cove Back
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| Name: Wonson Cove Back | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1100 month plus utilities Year Round* |
| Enjoy the privacy of a cul de sac on Rocky Neck with access to the water. This newly refurbished condo unit is attached to Front Cove.
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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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Scallop Cove
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| Name: Scallop Cove | Bedrooms: 2 | Bathrooms: 2 | SleepsMaximum: 6 | $2700/wk summer* |
| Rockport Cottage! This pristine 2 bedroom/2 bath home was carefully designed to provide for your every need from the bright designer kitchen with cathedral ceiling, sitting area and large island great for gathering family & friends, the formal dining room
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Changing Tides
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| Name: Changing Tides | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 5 | $1500/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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Resthaven
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| Name: Resthaven | Bedrooms: 4 | Bathrooms: 1.5 | SleepsMaximum: 6 | $2200/wk* |
| Rockport! This four bedroom 1.5 bath home is named well as it is a spacious and comfortable family home, located just one block from Old Garden Beach as well as just outside of the village with all its attractions.
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