| 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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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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Monarch Glen
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| Name: Monarch Glen | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $1800/mo+ winter; $2000/wk summer* |
| Less than half a mile from Gloucester's sandy Good Harbor Beach, this delightful property is nestled on a quiet half acre wooded lot, making it a perfect respite on a hot summer day!
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Commonwealth
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| Name: Commonwealth | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1250 month plus utilities* |
| YEAR ROUND RENTAL. This charming two bedroom newly renovated home is conveniently located near the commuter rail to Boston, downtown Gloucester and its picturesque harbor. This house is in walking distance of "The Boulevard" and Stage Fort Park.
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Friendly Views
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| Name: Friendly Views | Bedrooms: 3 | Bathrooms: 2.5 | SleepsMaximum: 6 | $2000/wk sum/$400 nite off 3 nite min* |
| This gleaming, immaculate home is perched above the sparkling waters of Gloucester's inner harbor. From the comfort of your sun porch or deck, watch the gulls following the fishing boats home with their catch and enjoy the lively nautical scene.
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Gap Head Cottage
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| Name: Gap Head Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1200-$1625/wk minimum 2 weeks* |
| This lovely and spacious free-standing two bedroom cottage overlooks one of Rockport's prettiest Coves.
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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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Wonson Cove
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| Name: Wonson Cove | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 8 | $3,500/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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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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Captain's Cottage
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| Name: Captain's Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 4 | $1,500* |
| This delightful pine-paneled cottage is located on a quiet Rockport lane just steps from Cape Hedge Beach. From its sun room/sleeping porch, you can enjoy views of the Atlantic or walk across the private footbridge to the beach.
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