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Sort By: NameBedroomsBathroomsSleepsMaximum 
Stoneacre
Name: StoneacreBedrooms: 11Bathrooms: 10SleepsMaximum: 20Please Inquire*
Direct waterfront estate is perfect for the ultimate upscale vacation rental, a family reunion, or a fully-equipped and comfortable venue for a corporate or organizational retreat, StoneAcre has it all! Sleeps 20+, 11 bedrooms, 6 full baths, 4 half baths.  Learn more...
Changing Tides
Name: Changing TidesBedrooms: 3Bathrooms: 2SleepsMaximum: 5$1500/month + winter; $1900/week summer*
Situated on the shores of the tidal Mill River on a shaded lot of nearly one acre in Gloucester's watery Riverview district, this newly renovated property has a private dock and float. Swim, fish, or row in the dinghy left for your use.  Learn more...
Between the Beaches Cottage
Name: Between the Beaches CottageBedrooms: 2.5Bathrooms: 2SleepsMaximum: 7$1500/wk summer*
Tucked away on a quiet lane between Rockport's Back and Front Beaches, this delightful cottage has been lovingly restored, with every attention paid to the details.  Learn more...
English Sea Gardens
Name: English Sea GardensBedrooms: 3Bathrooms: 1.5SleepsMaximum: 7$2900/wk summer*
Swimming pool! Old World charm describes this delightful three bedroom cottage nestled at the edge of a two acre oceanside estate. Thoughtfully furnished by its decorator owner, the cottage has a large eat-in fully applianced kitchen.  Learn more...
Friendly Views
Name: Friendly ViewsBedrooms: 3Bathrooms: 2.5SleepsMaximum: 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.  Learn more...
Cottage by the Sea
Name: Cottage by the SeaBedrooms: 3Bathrooms: 2SleepsMaximum: 6$2800-3200/wk summer*
This lovely 3 bedroom colonial sits on a quiet lane in Rockport's Pigeon Cove and offers sweeping views of Sandy Bay from the new deck. Guests of the house have use of the world class Ralph Waldo Emerson Inn's amenities.  Learn more...
Post & Beam
Name: Post & BeamBedrooms: 3Bathrooms: 3SleepsMaximum: 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!  Learn more...
Ingomar at Rockaway Condominiums
Name: Ingomar at Rockaway CondominiumsBedrooms: 2Bathrooms: 2SleepsMaximum: 4$2,000-$2600/mo +*
Delightful free standing home on the grounds of the Rockaway Condominium complex. Exceptional views of Gloucester Harbor and Ten Pound Island.  Learn more...
Cher Ami
Name: Cher AmiBedrooms: 2.5Bathrooms: 1SleepsMaximum: 4$4000/mo summer*
Welcome "dear friends" to this gleaming and immaculate, newly remodeled two plus bedroom unit which is available as a full season rental.  Learn more...
The Bright Side Cottage
Name: The Bright Side 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...
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