| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum |   |
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Star of the Sea
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| Name: Star of the Sea | Bedrooms: 3 | Bathrooms: 3 | SleepsMaximum: 8 | $3000/week* |
| Long Beach! Walk to two of Cape Ann's finest sandy beaches, restaurants and even an ice cream store from this tastefully and comfortably furnished three bedroom, three bath contemporary home. The perfect location for your ultimate Cape Ann vacation!
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Too Beach!
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| Name: Too Beach! | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 8 | $890/mo+ winter; $2200/wk sum* |
| "Location, location, location." Good Harbor Beach! This delightful 3 bedroom/1 bath cottage is almost on the sands of Gloucester's most coveted beach.
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Via Benevento
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| Name: Via Benevento | Bedrooms: 2 | Bathrooms: 2.5 | SleepsMaximum: 4 | $2200/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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Seascape
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| Name: Seascape | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 2 | $1900/mo plus utilties* |
| This immaculate 3 bedroom/ 2 full bath apartment in the heart of historic Rockport village has been impeccably maintained. The unit is so spacious, sunny and well laid out that it feels more like a house than an apartment.
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Good Harbor Getaway
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| Name: Good Harbor Getaway | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 4 | $650/wk summer* |
| This simple but private apartment is located on the ground floor of a summer home in Gloucester's prestigious Briar Neck neighborhood. From its shaded patio, you look out to its lovely perennial garden.
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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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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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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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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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Ivy Cottage
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| Name: Ivy Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1500/mo+ util winter* |
| East Gloucester. This delightful two bedroom English country-style cottage on an estate setting in has high ceilings, an oversized fireplace, a large and private yard with flower gardens, and lots of light.
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