| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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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 | $2000/week* |
| 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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Rockledge
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| Name: Rockledge | Bedrooms: 6 | Bathrooms: 4 | SleepsMaximum: 14 | $4400-$5000/wk consult realtor* |
| The name "Rockledge" aptly describes this spacious family home that is perched on a granite bluff overlooking the Atlantic and Rockport's famous twin lighthouses.
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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. It has 2 bedrooms and 1.5 baths. A charming enclosed outside area with seating for four and a grill.
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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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Lily Pond Farm
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| Name: Lily Pond Farm | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $1800/wk summer* |
| This lovelythree bedroom/ two bath victorian brings you back to the era when life was more serene and relaxed. Set in an idyllic and private area with woods on two sides and overlooking a glimmering pond forget it is the twenty first century!
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The Galley
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| Name: The Galley | Bedrooms: 0 | Bathrooms: 1 | SleepsMaximum: 2 | $950/wk summer* |
| Waterfront! Adorable studio cottage right on Smith Cove. Everything you need in one room: a queen bed, a rocking chair sofa, fireplace, stack washer and dryer, new galley kitchen, full bath (tub with shower) and most of all an exquisite verandah with co
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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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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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Magellan's Way
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| Name: Magellan's Way | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $1400/mo + util year round* |
| This lovely, secluded ranch home with a large private yard is set at the end of a hidden drive in East Gloucester on a wooded lot. It is available year round.
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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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