| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Beacon Hill
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| Name: Beacon Hill | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1200/mo+ YR* |
| YEAR ROUND: A charming little house set back from the street in downtown Gloucester offers a short walk to the train station, city hall, library, restaurants, harbor and so much more.
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Garden by the Sea
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| Name: Garden by the Sea | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1000/mo + winter; $1250/wk summer* |
| Relax and enjoy the wonderful views looking out over Gloucester's beautiful Good Harbor Beach and Thachers Island from this bright and delightfully furnished two bedroom apartment.
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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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Sunny Ledges
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| Name: Sunny Ledges | Bedrooms: 4 | Bathrooms: 3 | SleepsMaximum: 6 | $2000 mo+ winter* |
| Enjoy lovely ocean views from this sunny, contemporary four bedroom/ 3 bath home built in 2000. The house is on a quiet cul de sac surrounded by lovely perennial beds which can be enjoyed from any of the 4 decks. Available as an off season rental October-
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Arcadia House
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| Name: Arcadia House | Bedrooms: 3 | Bathrooms: 3 | SleepsMaximum: 6 | $2000/mo + winter; $3000/wk summer* |
| This wonderful Rockport house, formerly an artist's studio, has recently been renovated into a luxury vacation home. High ceilings, white walls, spacious rooms, harbor views, and plenty of parking are just some of its distinguishing features.
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Rosemarc House
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| Name: Rosemarc House | Bedrooms: 3 | Bathrooms: 3.5 | SleepsMaximum: 6 | $6000/week* |
| Good Harbor BEACHFRONT! Private access to beach directly from this elegant 3 bedroom/3.5 bath contemporary with custom granite kitchen, home gym, and the best views and beach access on Cape Ann. This is the beach house you have been waiting for-call today!
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Front Beach Condo
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| Name: Front Beach Condo | Bedrooms: 2 | Bathrooms: 1.5 | SleepsMaximum: 6 | $1400/mo+ winter (3 month minimum)* |
| Rockport! This delightful sunny two bedroom condominium has views of the beach and the ideal location with off street parking for one car, just steps from Front Beach in Rockport as well as in the heart of the best that the village has to offer...
There i
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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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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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Ocean Bluff
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| Name: Ocean Bluff | Bedrooms: 4 | Bathrooms: 3.5 | SleepsMaximum: 8 | $2500/mo+ winter or $5,000/wk summer* |
| Rockport! Swimming pool! This oceanfront home in the coveted 'Avenues' section of Rockport's Pigeon Cove offers glorious views and all the comforts of home in a spacious and very private quiet setting.
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