| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Ipswich Bay House
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| Name: Ipswich Bay House | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 8 | $1900/month + winter* |
| This spacious, beautiful contemporary home (2500 sf) in an estate setting in Gloucester's coveted Annisquam district has private sandy beaches (shared by a lucky few), boating and a fresh water pond just outside the door.
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Eden Lights
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| Name: Eden Lights | Bedrooms: 7 | Bathrooms: 2.5 | SleepsMaximum: 14 | $6000/wk summer* |
| Oceanfront! Welcome to this inviting renovated property built a century ago at the edge of Rockport's rugged Atlantic coastline. Once you enter its spacious living room with fireplace and walk out onto its wraparound porch, you will never want to leave!
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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 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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Wiley's Way
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| Name: Wiley's Way | Bedrooms: 2 | Bathrooms: 1.5 | SleepsMaximum: 4 | $1600/week* |
| A charming cottage located in Gloucester's fabled artist colony of Rocky Neck, on a quiet side street. Two bedrooms and 1.5 baths. Enjoy the great room and the private and enclosed outside area with seating for four and a grill.
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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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Beach Stone Cottage
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| Name: Beach Stone Cottage | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $2000/month plus util $3500/wk summer* |
| 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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Via Benevento
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| Name: Via Benevento | Bedrooms: 2 | Bathrooms: 2.5 | SleepsMaximum: 4 | $2200/month plus util. year round* |
| FURNISHED YEAR ROUND RENTAL: Newly constructed 2 bedroom, 2.5 bath condominium in the historic West End of Main Street in downtown Gloucester...
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Red Roof
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| Name: Red Roof | Bedrooms: 5 | Bathrooms: 2.75 | SleepsMaximum: 10 | Speak to your realtor* |
| A.Piatt Andrew Jr.(1873-1936) visionary, statesman, Harvard Economist, officer of WWI as well as architect and designer of the waterfront gem he called “Red Roof” on Gloucester’s Eastern Point. The visitor is offered a glimpse of his intensity of vision...
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Labor of Love
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| Name: Labor of Love | Bedrooms: 4 | Bathrooms: 2.5 | SleepsMaximum: 7 | $2650/wk* |
| Air conditioning! This immaculate and gracious 4+ bed/2.5 bath Rockport village home has been completely renovated with taste and style. Walk to the charming shops, galleries. restaurants and beaches. New granite kitchen and wonderful private yard.
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