| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Brightside Cottage
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| Name: Brightside Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 6 | $1000/month+ winter* |
| Only a half-mile (an easy walk) to the pristine white sands of Gloucester's Good Harbor Beach, this immaculate 2 bedroom ranch house comfortably sleeps six. Located in a quiet neighborhood the cottage is the perfect place to wind down after a long day at
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Wessex Cottage
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| Name: Wessex Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1350/month plus utilities* |
| 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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SeaCrest Guest House
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| Name: SeaCrest Guest House | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $2500/week* |
| This romantic gem is perched above the sea with incredible panoramic views of the Atlantic. Perfect for two, the cottage is tucked away on the grounds of the Seacrest Estate in beautiful Manchester by the Sea.
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Twilight Cottage
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| Name: Twilight Cottage | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 7 | $1600/mo+ utilities* |
| This 3+ bedroom/2 bath pristine cottage on Gloucester's picturesque Briar Neck overlooks and is steps from the white sands of Long Beach. The popular Good Harbor Beach is also just a short stroll away.
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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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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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Victorian House
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| Name: Victorian House | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $2600/wk summer* |
| Newly renovated with taste and style, this elegant Victorian home is located in Gloucester's fabled artist colony of Rocky Neck, on a quiet side street. Linger on its sweet front porch with harbor views.
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Wonson Cove
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| Name: Wonson Cove | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 8 | $1950/mo+ winter ($1800/wk) $3500/wk* |
| Waterfront! Swim from house! Views of Eastern Point and picturesque Dog Bar Breakwater! Lighthouses! Sunrise!You can experience all of these exclamations and never leave the Rocky Neck waterfront vacation home!
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Bass Rocks
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| Name: Bass Rocks | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $4800/month summer* |
| Tucked away behind the friendly owner's home, this attached East Gloucester cottage is a perfect retreat after a day of lounging on Good Harbor Beach, less than 1/4 mile away. Its separate driveway, perennial gardens and lawn provide shade and privacy.
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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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