| 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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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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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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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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Nautilus House
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| Name: Nautilus House | Bedrooms: 3 | Bathrooms: 2.5 | SleepsMaximum: 6 | $1600/mo plus utilities* |
| Location! Location! Location! Walk out the door of this newly remodeled beach townhouse, cross over the footbridge and voila you are on Good Harbor Beach, one of Gloucester's finest beaches. Views abound from almost every room. From the ample deck and sc
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Stowe Farm
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| Name: Stowe Farm | Bedrooms: 3 | Bathrooms: 3 | SleepsMaximum: 7 | $6,000/mo summer $5,000/mo shoulder* |
| Pastoral and privately situated on 200 rolling acres this newly built, 3 bed/3 bath high quality home is part of an historic estate in Essex and close enough to Route 128 to be an easy commute to Boston.
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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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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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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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Ipswich Bay House
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| Name: Ipswich Bay House | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 8 | $1900/month + winter* |
| This spacious, beautiful contemporary home (2500 sf) in an estate setting in Gloucester's coveted Annisquam district has private sandy beaches (shared by a lucky few), boating and a fresh water pond just outside the door.
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