| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Jonathan Cook House
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| Name: Jonathan Cook House | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 5 | $1200/month includes heat,year round* |
| This charming 3 plus bedroom apartment is in an historic 2 family home in the heart of picturesque Rockport, a short walk from the Boston train.
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Beach Stone Cottage
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| Name: Beach Stone Cottage | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $3200/wk or $12K/mo* |
| Good Harbor Beach! Updated and comfortable with views this 3 bedroom/2 full bath home boasts a large modern kitchen, two spacious sitting rooms a private yard-all just feet off the white sands of Good Harbor Beach.
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Victorian House
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| Name: Victorian House | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $2000/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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Twilight Cottage
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| Name: Twilight Cottage | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 7 | $2500/wk summer* |
| 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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Orchard Ledge
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| Name: Orchard Ledge | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 2 | $1000/wk summer* |
| This charming, immaculate year round private entrance apartment is attached to a lovely home in an estate setting in idyllic East Gloucester.
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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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Cottage on the Lane
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| Name: Cottage on the Lane | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | call for off season rates $2500/wk sum* |
| Leave your car in the driveway of this newly renovated and completely refurbished oceanview home and enjoy Cape Ann. Wander the quaint lanes of Rockport and browse at its many art galleries and boutiques on famed Bearskin Neck.
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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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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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Sunset Cottage
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| Name: Sunset Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1850/wk summer, monthly rates available* |
| Named for the magnificent sunsets that can be enjoyed from inside on the sun porch, or outside on one of two decks, this delightful and completely renovated waterfront cottage is in Gloucester's relaxed Riverdale district.
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