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Sort By: NameBedroomsBathroomsSleepsMaximum 
Cottage on the Mill Pond
Name: Cottage on the Mill PondBedrooms: 3Bathrooms: 1SleepsMaximum: 6$2250/wk for 2 wks or $2500/wk*
Leave your car in the driveway of this beautifully decorated home and enjoy Cape Ann on foot or on bicycle. Wander the quaint lanes of Rockport and browse at its many art galleries and boutiques on famed Bearskin Neck.  Learn more...
Wessex Cottage
Name: Wessex CottageBedrooms: 2Bathrooms: 1SleepsMaximum: 4$1350/month plus utilities*
This enchanting 2 bedroom/1 bath, single level cape is a five minute walk from 2 beautiful beaches in Rockport's charming South End. There are ocean views, and a large lot with plenty of Cape Ann's signature granite outcroppings.  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...
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...
Annie's Place
Name: Annie's PlaceBedrooms: 3Bathrooms: 1SleepsMaximum: 6$1200/week summer*
This delightful home in Gloucester's picturesque Bay View district and is full of sun and warmth. A five minute walk brings you to the neighborhood beach of Plum Cove which along with great swimming offers a good chance of a tiny hermit crab sighting.  Learn more...
Bottom's Up
Name: Bottom's UpBedrooms: 2Bathrooms: 1SleepsMaximum: 4$1000/wk summer*
"Bottom’s Up!” This two bedroom one bath hidden gem is located in the heart of the historic and scenic North Shore in Beverly. Nestled in a cul de sac, it’s a little off the beaten path, while still allowing easy access to Gloucester, Rockport, Manchester  Learn more...
Good Harbor Hideaway
Name: Good Harbor HideawayBedrooms: 4Bathrooms: 2.5SleepsMaximum: 6$1800/mo+ winter*
This delightful newer Gloucester home is just a stone's throw to Good Harbor Beach. Set on a quiet residential lane, it offers ocean views across a scenic marsh.  Learn more...
SeaCrest Estate
Name: SeaCrest EstateBedrooms: 8Bathrooms: 7.5SleepsMaximum: 14please inquire*
This spectacular 4.2 acre estate on Manchester-by-the Sea's lovely Smiths Point offers the ultimate in oceanfront luxury and the perfect surroundings for your wedding or special event.  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...
Spindrift
Name: SpindriftBedrooms: 4.5Bathrooms: 2.75SleepsMaximum: 10$3750/wk or $2000/mo + util*
Direct waterfront, Rockport South End & central air! A spindrift is windblown seaspray which is a regular sighting at this lovely home that is as close to the Atlantic as the ocean will allow...  Learn more...
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