| 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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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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The Galley
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| Name: The Galley | Bedrooms: 0 | Bathrooms: 1 | SleepsMaximum: 2 | $1000/mo+ winter* |
| Waterfront! Adorable studio cottage right on Smith Cove. Everything you need in one room: a queen bed, a rocking chair sofa, fireplace, stack washer and dryer, new galley kitchen, full bath (tub with shower) and most of all an exquisite verandah with co
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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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Harbor Breezes
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| Name: Harbor Breezes | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1400/mo includes heat* |
| Rockport Year round! Incredible Water Views! This large two bedroom unit is on the third floor of a waterfront building in the heart of quaint Rockport. Combination living/dining rooms have lovely views of Front Beach and Sandy Bay beyond. Heat included.
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West Wind
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| Name: West Wind | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 9 | $3500/wk summer/ $2200/mo+ winter* |
| Overlooking the Ipswich Bay in Annisquam, this tastefully renovated ranch is comfortable and pretty with some of the best views on Cape Ann!
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Seven Knots
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| Name: Seven Knots | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $2000/mo includes util or $32K for summe* |
| Standing in the living room of this cottage is just as close to be floating as one can be without a boat! Spectacular views from every corner of the house.
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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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The Red House
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| Name: The Red House | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 5 | $1800/wk summer* |
| Walk to Singing Beach (1/2 mile) or into town (1 mile) from this sweet, newly refurbished comfortable home in the incomparable Smith's Point area of lovely Manchester-by-the Sea.
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Emerson Cottage
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| Name: Emerson Cottage | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $3500/wk July, $3900/wk August* |
| This charming 3 bedroom/1.5 bath home in the Pigeon Cove section of Rockport has glorious views of Sandy Bay. Sit on the spacious wraparound porch, in the hot tub large enough for six, or splash in the freshwater pool next door at the Inn...
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