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Sort By: NameBedroomsBathroomsSleepsMaximum 
Squam Rock
Name: Squam RockBedrooms: 4Bathrooms: 2SleepsMaximum: 8$1300/month plus utilities*
WINTER RENTAL AVAILABLE SEPTEMBER 11TH TO MAY 31, 2009. This lovely, antique, three plus bedroom house has glimpses of Lobster Cove since it sits at the head of the picturesque harbor in Gloucester's historic village of Annisquam.  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...
Look on the Brightside
Name: Look on the BrightsideBedrooms: 2.5Bathrooms: 2.5SleepsMaximum: 6$2000/week*
Walk to Good Harbor Beach (3/10 mile) from this luxurious and spacious 2.5 bedroom/2.5 bath condominium/townhouse overlooking the picturesque city of Gloucester. Central air conditioning, hardwood and tile and gleaming granite kitchen and baths...  Learn more...
Poet's Cove
Name: Poet's CoveBedrooms: 2Bathrooms: 1.5SleepsMaximum: 4$1500/wk summer*
Extraordinary views of Sandy Bay from this 2 bedroom 'half a house' in Rockport's quiet and lovely 'Avenues' area of Pigeon Cove have been known to stimulate the poetic side of its inhabitants.  Learn more...
Ferry Hill Landing
Name: Ferry Hill LandingBedrooms: 3Bathrooms: 2SleepsMaximum: 6$3500/wk summer; $2000/mo+winter*
This is a boater's delight in Gloucester's watery Riverview district! Bring your forty footer and tie up to the deep water dock right at the house. Kayaks and skiffs are also welcome.  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...
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...
Bass Rocks
Name: Bass RocksBedrooms: 1Bathrooms: 1.5SleepsMaximum: 2$4800/mo, $1200/wk summer*
Tucked away behind the friendly owner's home, this attached East Gloucester cottage is a perfect retreat after a day of lounging on Good Harbor Beach, less than 1/4 mile away. Its separate driveway, perennial gardens and lawn provide shade and privacy.  Learn more...
Stone Mansion
Name: Stone MansionBedrooms: 10Bathrooms: 6.5SleepsMaximum: 18$6500/week contact realtor*
Go back in time to the Civil War era when Brig. General Greely Curtis came to Manchester by the Sea to build his mansion on a high bluff overlooking the Atlantic, with the Boston skyline and the Cape Cod shore visible in the distance.  Learn more...
A Flume House
Name: A Flume HouseBedrooms: 4Bathrooms: 2.5SleepsMaximum: 7$1675/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...
1-10 of 128NextLast


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