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Sort By: NameBedroomsBathroomsSleepsMaximum 
Western Avenue
Name: Western AvenueBedrooms: 2Bathrooms: 2SleepsMaximum: 4$1500/mo+ util.*
Water Views! Year Round. Beautifully renovated two level apartment in a two unit building just across from Gloucester Harbor. Walk to town, beach, boating and stores.  Learn more...
Scallop Cove
Name: Scallop CoveBedrooms: 2Bathrooms: 2SleepsMaximum: 6$2700/wk summer*
Rockport Cottage! This pristine 2 bedroom/2 bath home was carefully designed to provide for your every need from the bright designer kitchen with cathedral ceiling, sitting area and large island great for gathering family & friends, the formal dining room  Learn more...
Sunny Ledges
Name: Sunny LedgesBedrooms: 4Bathrooms: 3SleepsMaximum: 6$2000 mo+ winter*
Enjoy lovely ocean views from this sunny, contemporary four bedroom/ 3 bath home built in 2000. The house is on a quiet cul de sac surrounded by lovely perennial beds which can be enjoyed from any of the 4 decks. Available as an off season rental October-  Learn more...
Little Red House
Name: Little Red HouseBedrooms: 3Bathrooms: 1SleepsMaximum: 5$1200/wk summer; $1200/mo + util. winter*
Enjoy this comfortable 3 bedroom, 1 full bath colonial just steps away from Gloucester's historic Stage Fort Park which was once a landing place for pirates, now a venue for free concerts, fireworks and so mucn more!  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...
The Point
Name: The PointBedrooms: 5Bathrooms: 2.5SleepsMaximum: 10$2800/mo+ util. winter; $6000/wk summer*
Swimming pool and waterfront! This classic New England home, in Gloucester's aptly named Riverview district, has been recently renovated and professionally decorated for style and comfort. Situated 1.5 private acres overlooking the Annisquam River.  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...
SeaCrest Guest House
Name: SeaCrest Guest HouseBedrooms: 1Bathrooms: 1.5SleepsMaximum: 2$2500/week*
This romantic gem is perched above the sea with incredible panoramic views of the Atlantic. Perfect for two, the cottage is tucked away on the grounds of the Seacrest Estate in beautiful Manchester by the Sea.  Learn more...
Sea Queen Condo
Name: Sea Queen CondoBedrooms: 2Bathrooms: 2SleepsMaximum: 4$2200/week (four week min.)*
This brand new, immaculate 2 bedroom/2 bath condominium offers all the high end amenities and is just one short block from Good Harbor Beach! Central airconditioning, Hardwood and tile and gleaming granite kitchen and baths, gas fireplaced living room...  Learn more...
Gull Cottage
Name: Gull CottageBedrooms: 3Bathrooms: 1.5SleepsMaximum: 6$2500/wk*
Views abound from this beautiful home in Gloucester's quiet Magnolia district which has been graciously decorated with style and flair and a constant mind for comfort. Floor to ceiling windows, three air conditioned bedrooms and 1.5 baths.  Learn more...
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