| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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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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Look on the Brightside
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| Name: Look on the Brightside | Bedrooms: 2.5 | Bathrooms: 2.5 | SleepsMaximum: 6 | Please inquire about availability/rates* |
| Walk to Good Harbor Beach (3/10 mile) from this luxurious and spacious 2.5 bedroom/2.5 bath condominium/townhouse overlooking the picturesque city of Gloucester. Central air conditioning, hardwood and tile and gleaming granite kitchen and baths...
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Poet's Cove
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| Name: Poet's Cove | Bedrooms: 2 | Bathrooms: 1.5 | SleepsMaximum: 4 | $1500/wk summer* |
| Extraordinary views of Sandy Bay from this 2 bedroom 'half a house' in Rockport's quiet and lovely 'Avenues' area of Pigeon Cove have been known to stimulate the poetic side of its inhabitants.
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Cottage on the Mill Pond
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| Name: Cottage on the Mill Pond | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | $2250/wk for 2 wks or $2500/wk* |
| Leave your car in the driveway of this beautifully decorated home and enjoy Cape Ann on foot or on bicycle. Wander the quaint lanes of Rockport and browse at its many art galleries and boutiques on famed Bearskin Neck.
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Lenart House
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| Name: Lenart House | Bedrooms: 4 | Bathrooms: 1.5 | SleepsMaximum: 7 | $1200-2100/wk 2 week minimum* |
| This turn of the century farmhouse is set on over an acre of privacy in Rockport's peaceful and salty South End. It has the ambiance of rural country with its classic New England fieldstone walls and interior fireplace.
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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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A Flume House
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| Name: A Flume House | Bedrooms: 4 | Bathrooms: 2.5 | SleepsMaximum: 7 | $1450/mo+ winter* |
| Central airconditioning!This immaculate, gleaming and spacious contemporary has views of the Atlantic from almost every window. Four bedrooms and 2.5 baths, lovely manicured grounds, decks and plenty of parking.
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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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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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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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