| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Tranquility
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| Name: Tranquility | Bedrooms: 4 | Bathrooms: 3 | SleepsMaximum: 10 | $4000/wk summer* |
| Dock, central airconditioning and swim from home! Bring your boat and dock it in front of this gracious and immaculate waterfront 4 bedroom/3 bath home. Exquisite attention to detail with the emphasis on comfort, relaxation and recreation. WINTER available
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Wonson Cove Front
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| Name: Wonson Cove Front | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 5 | $1800/wk sum; $1500/mo+ winter* |
| From the shaded porch of this newly renovated property, you can enjoy your al fresco meals with the shores of Wonson's Cove just beyond. Newly polished hardwood floors and open floor plan give this a light and sunfilled feeling. The living room has a firep
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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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Granite Courtyard
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| Name: Granite Courtyard | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 2 | $800-900/wk* |
| This imaginatively decorated home, charmingly located in Rockport's quaint Pigeon Cove neighborhood, is built on the site of a former ox barn, to create a unique vacation retreat.
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Coincide Studio
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| Name: Coincide Studio | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 4 | $850/wk summer* |
| This bright and sunny lower level, refurbished studio apartment is just steps from the white sands of Gloucester's fabulous Good Harbor Beach!
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Lily Pond Farm
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| Name: Lily Pond Farm | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $1500/mo+ win OR $1800/mo yr $1800/wk* |
| 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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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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Rosemarc House
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| Name: Rosemarc House | Bedrooms: 3 | Bathrooms: 3.5 | SleepsMaximum: 6 | $6000/week* |
| Good Harbor BEACHFRONT! Private access to beach directly from this elegant 3 bedroom/3.5 bath contemporary with custom granite kitchen, home gym, and the best views and beach access on Cape Ann. This is the beach house you have been waiting for-call today!
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Eastern Point Ocean Vista
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| Name: Eastern Point Ocean Vista | Bedrooms: 5 | Bathrooms: 3 | SleepsMaximum: 10 | $5000/wk summer (Friday)* |
| New listing-Pool! Air conditioning! Located on Gloucester's prestigious Eastern Point, Eastern Point Ocean Vista offers views, privacy and passes to beautiful Brace Cove, a sandy beach in walking distance of the house. 5 bedrooms, 3 full baths...
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Sea Street
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| Name: Sea Street | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $1800/mo + utilities* |
| Manchester-by-the-Sea! This bright, newly renovated 3 bed/1.5 bath half a house is a short walk to the white sands of Singing Beach and 1 block from Manchester-by-the-Sea's famous sailboat-filled harbor.
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