| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Wessex Cottage
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| Name: Wessex Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1350/wk summmer (2 wk min)* |
| This enchanting 2 bedroom/1 bath, single level cape is a five minute walk from 2 beautiful beaches in Rockport's charming South End. There are ocean views, and a large lot with plenty of Cape Ann's signature granite outcroppings.
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The Grey House
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| Name: The Grey House | Bedrooms: 5 | Bathrooms: 4 | SleepsMaximum: 8 | $2750/wk summer* |
| This completelly renovated house in lovely Manchester-by-the-Sea has hardwood floors throughout, 5 bedrooms and 4 full sparkling new baths, a new granite kitchen, living room with two sided fireplace, dining area, and a large screen porch.
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Rocky Neck Vista
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| Name: Rocky Neck Vista | Bedrooms: 2 | Bathrooms: 2 | SleepsMaximum: 4 | $1500/wk summer* |
| This two bedroom two bath home is located in the heart of Gloucester's Rocky Neck which is the oldest art colony in the country. Recent updates to the property only enhance the views from the house which extend over rooftops to Smith's Cove and the harbor
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The Enclave
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| Name: The Enclave | Bedrooms: 4 | Bathrooms: 2.5 | SleepsMaximum: 6 | $3000/mo plus utilities* |
| This stunning waterfront four bedroom contemporary is situation directly on the eastern shore of Gloucester Harbor and is available for year round rental. Swim from the property or paddle your kayak right from home.
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The Hideout
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| Name: The Hideout | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 4 | $1150/week* |
| Bring your boat and swim from this immaculate cottage that makes you feel as if you are floating in a well appointed vessel not only because of the view, but also the ingenious use of space, with many built-ins and the overall innovative decor.
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Sol Cottage
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| Name: Sol Cottage | Bedrooms: 1 | Bathrooms: 2 | SleepsMaximum: 2 | $2400/2 wks or $4,500/mo* |
| Walk to beach and views! This comfortable one bedroom home in Gloucester's Lanesville district, boasts gorgeous views of Ipswich Bay, with its fabulous sunsets and a short walk to a sandy beach.
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Addison Proctor House Condo
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| Name: Addison Proctor House Condo | Bedrooms: 3 | Bathrooms: 2.5 | SleepsMaximum: 9 | $2500/wk or $2000/multiple wks* |
| Enjoy stunning views of Gloucester’s outer harbor from this recently restored, elegant 3 bedroom/2.5 bath condominium located on historic Stacey Boulevard. Tastefully furnished with all the modern amenities-you'll never want to leave Cape Ann!
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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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Sunny Beach
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| Name: Sunny Beach | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | 3 weeks left--REDUCED RATE $1800/week.* |
| This light-filled and airy home is on the marsh with expansive views looking out towards Good Harbor Beach, one of Gloucester's finest sandy beaches which is just a few minutes walk away.
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Annie's Place
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| Name: Annie's Place | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | $1200/week summer* |
| This delightful home in Gloucester's picturesque Bay View district and is full of sun and warmth. A five minute walk brings you to the neighborhood beach of Plum Cove which along with great swimming offers a good chance of a tiny hermit crab sighting.
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