| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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Buoy 23
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| Name: Buoy 23 | Bedrooms: 4 | Bathrooms: 1.5 | SleepsMaximum: 7 | $2750/week summer* |
| Waterfront with dock this gem has four beds and 1.5 baths, a deepwater dock (for up to a 20' boat) and a wrap around screened porch. Swim from dock, shore or sand bar.
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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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Windward
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| Name: Windward | Bedrooms: 4 | Bathrooms: 3 | SleepsMaximum: 8 | $7500/wk summer* |
| Beachfront! The white sands of Long Beach await you just steps from this spectacular four bedroom three bath contemporary treasure! Boasting expansive views of the world famous Twin Lighthouses of Rockport and beyond to the open Atlantic...
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Carrie Lane House
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| Name: Carrie Lane House | Bedrooms: 3 | Bathrooms: 2 | SleepsMaximum: 5 | $1800/mo plus utilities year round* |
| This custom built 3 bedroom 2 bath home has many wonderful and unique features and is in excellent condition making it the right choice for your year round rental home. $1800/mo plus utilities year round.
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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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Rockport Village House
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| Name: Rockport Village House | Bedrooms: 3 | Bathrooms: 2.5 | SleepsMaximum: 8 | $1800/wk summer; $1200/week winter* |
| This immaculate and charming village gem offers versatility, style and convenience. A short walk to all that Rockport has to offer this 3 bedroom/ 2.5 bath home has quaint historic details, yet offers all modern conveniences and comforts with newly remode
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Harry's Hideaway
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| Name: Harry's Hideaway | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 2 | $1000/month+* |
| Rockport Year round! This quaint and historic 2 bed/1 bath year round rental home is in town, but feels like it is in the country! You don't need a car to live at this property as the train, shopping and two beaches are all within a 5 miniute walk...
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King Street Inn
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| Name: King Street Inn | Bedrooms: 4 | Bathrooms: 4 | SleepsMaximum: 10 | $2000/wk summer* |
| Rockport! Steps off of Front Beach! Sleeps 10! This 4 bedroom 4 bath home is located on a lovely historic street in the picturesque village of Rockport within walking distance to the many shops, restaurants and galleries. Each bedroom has a kitchenette an
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Quarryman's Cottage
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| Name: Quarryman's Cottage | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 2 | $700/+ taw* |
| Exceptional views of Ipswich Bay and the Massachusetts and New Hampshire coastlines abound from this charming year-round quarryman's cottage in Gloucester's Bay View neighborhood.
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Annie's Place
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| Name: Annie's Place | Bedrooms: 3 | Bathrooms: 1 | SleepsMaximum: 6 | $1200/week summer* |
| This delightful home in Gloucester's picturesque Bay View district and is full of sun and warmth. A five minute walk brings you to the neighborhood beach of Plum Cove which along with great swimming offers a good chance of a tiny hermit crab sighting.
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