| 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 | $1500/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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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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Ferry Hill Landing
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| Name: Ferry Hill Landing | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 6 | $3500/wk summer; $2000/mo+winter* |
| This is a boater's delight in Gloucester's watery Riverview district! Bring your forty footer and tie up to the deep water dock right at the house. Kayaks and skiffs are also welcome.
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Post & Beam
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| Name: Post & Beam | Bedrooms: 3 | Bathrooms: 3 | SleepsMaximum: 8 | $2750/wk summer* |
| This very special, private & lovely, owner-built, post & beam house is centrally located in historic and quaint downtown Rockport, offering a surprisingly spacious living area for your ideal vacation getaway!
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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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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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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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Bearskin Cove Escape
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| Name: Bearskin Cove Escape | Bedrooms: 1 | Bathrooms: 1 | SleepsMaximum: 4 | $1200/mo + winter* |
| Tucked away behind Rockport's quaint shops and restaurants, the perfect oasis awaits you! This perfectly renovated waterfront hideaway has everything you will need for your vacation--summer breezes, a quiet perch to enjoy sunsets over the water,
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Hobbs Court
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| Name: Hobbs Court | Bedrooms: 2.5 | Bathrooms: 1.5 | SleepsMaximum: 4 | $1600/mo + utilities Year Round* |
| Situated on a quiet cul de sac in Essex, this completely renovated and lead free 2 plus bedroom/1.5 bath year round home awaits you! Gleaming hardwood floors grace the living and formal dining rooms while the NEW stainless steel kitchen is tiled.
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Sea Street
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| Name: Sea Street | Bedrooms: 3 | Bathrooms: 1.5 | SleepsMaximum: 6 | $1800/mo + utilities* |
| Manchester-by-the-Sea! This bright, newly renovated 3 bed/1.5 bath half a house is a short walk to the white sands of Singing Beach and 1 block from Manchester-by-the-Sea's famous sailboat-filled harbor.
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