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Sort By: NameBedroomsBathroomsSleepsMaximum 
The Enclave
Name: The EnclaveBedrooms: 4Bathrooms: 2.5SleepsMaximum: 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.  Learn more...
Monarch Glen
Name: Monarch GlenBedrooms: 3Bathrooms: 1.5SleepsMaximum: 6$1495/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!  Learn more...
Brightside Cottage
Name: Brightside CottageBedrooms: 2Bathrooms: 1SleepsMaximum: 6$1000/month+ winter*
Only a half-mile (an easy walk) to the pristine white sands of Gloucester's Good Harbor Beach, this immaculate 2 bedroom ranch house comfortably sleeps six. Located in a quiet neighborhood the cottage is the perfect place to wind down after a long day at  Learn more...
Cottage on the Lane
Name: Cottage on the LaneBedrooms: 3Bathrooms: 1SleepsMaximum: 6call for off season rates $2500/wk sum*
Leave your car in the driveway of this newly renovated and completely refurbished oceanview home and enjoy Cape Ann. Wander the quaint lanes of Rockport and browse at its many art galleries and boutiques on famed Bearskin Neck.  Learn more...
The Grey House
Name: The Grey HouseBedrooms: 5Bathrooms: 4SleepsMaximum: 8$2750/wk summer*
This completelly renovated house in lovely Manchester-by-the-Sea has hardwood floors throughout, 5 bedrooms and 4 full sparkling new baths, a new granite kitchen, living room with two sided fireplace, dining area, and a large screen porch.  Learn more...
A Flume House
Name: A Flume HouseBedrooms: 4Bathrooms: 2.5SleepsMaximum: 7$1450/mo+ winter*
Central airconditioning!This immaculate, gleaming and spacious contemporary has views of the Atlantic from almost every window. Four bedrooms and 2.5 baths, lovely manicured grounds, decks and plenty of parking.  Learn more...
Front Beach Condo
Name: Front Beach CondoBedrooms: 2Bathrooms: 1.5SleepsMaximum: 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  Learn more...
Wonson Cove Front
Name: Wonson Cove FrontBedrooms: 2Bathrooms: 1SleepsMaximum: 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  Learn more...
Wonson Cove
Name: Wonson CoveBedrooms: 4Bathrooms: 2SleepsMaximum: 8$1950/mo+ winter ($1800/wk) $3500/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!  Learn more...
Belle View
Name: Belle ViewBedrooms: 6Bathrooms: 5SleepsMaximum: 18$2950-$6500/wk or $3000/mo + off*
This spacious and gracious center stair colonial offers incredible versatility to suit your specific vacation needs. The house can be rented in various incarnations to sleep from 8 to 16+ people, making it the perfect getaway.  Learn more...
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