| Sort By: | Name | Bedrooms | Bathrooms | SleepsMaximum | |
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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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Magnolia Pied a Terre
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| Name: Magnolia Pied a Terre | Bedrooms: 2 | Bathrooms: 1.5 | SleepsMaximum: 6 | $1800/month including util.* |
| Magnolia! 2 minute walk to a sandy beach, this sparkling modern 2 bedroom, 1.5 bath townhouse is in the perfect location for a New England beach vacation. Enjoy breathtaking views of Magnolia Harbor and Gray Beach. Available as a winter rental September 1
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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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Wonson Cove Front
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| Name: Wonson Cove Front | Bedrooms: 2 | Bathrooms: 1 | SleepsMaximum: 5 | $1800/wk sum; $1500/mo+ winter* |
| From the shaded porch of this newly renovated property, you can enjoy your al fresco meals with the shores of Wonson's Cove just beyond. Newly polished hardwood floors and open floor plan give this a light and sunfilled feeling. The living room has a firep
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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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Magnolia Sunsets
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| Name: Magnolia Sunsets | Bedrooms: 3 | Bathrooms: 2.5 | SleepsMaximum: 6 | $3800/week call re:off season rates* |
| Waterfront & walk to beach! This direct oceanfront 3 bedroom/2.5 bath charmer was conceived in 1847 but completely, and beautifully, reconceived in 2004 retaining its old world ambiance with the modern amenities and details a discerned guest should expect.
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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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Seven Knots
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| Name: Seven Knots | Bedrooms: 1 | Bathrooms: 1.5 | SleepsMaximum: 2 | $2000/mo includes util or $32K for summe* |
| Standing in the living room of this cottage is just as close to be floating as one can be without a boat! Spectacular views from every corner of the house.
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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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West Wind
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| Name: West Wind | Bedrooms: 4 | Bathrooms: 2 | SleepsMaximum: 9 | $3500/wk summer/ $2200/mo+ winter* |
| Overlooking the Ipswich Bay in Annisquam, this tastefully renovated ranch is comfortable and pretty with some of the best views on Cape Ann!
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