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Sort By: NameBedroomsBathroomsSleepsMaximum 
Labor of Love
Name: Labor of LoveBedrooms: 5Bathrooms: 3.5SleepsMaximum: 9$2750/wk + $750/wk for apartment*
Air conditioning! This immaculate and gracious 4+ bed/3+ bath Rockport village home has been completely renovated with taste and style. Walk to the charming shops, galleries. restaurants and beaches of Rockport village! New granite kitchen and additional  Learn more...
Bearskin Neck Suite
Name: Bearskin Neck SuiteBedrooms: 3Bathrooms: 1SleepsMaximum: 5$1200/wk, $200/night off season*
Nestled in the heart of charming Rockport village, this second floor suite of rooms is cozy and comfortable. There are views of the harbor and Motif #1, and parking for 1 car.  Learn more...
Rocky Neck Vista
Name: Rocky Neck VistaBedrooms: 2Bathrooms: 2SleepsMaximum: 6$1500/wk summer; $1200/month + util. win*
This two bedroom two bath home is located in the heart of Gloucester's Rocky Neck which is the oldest art colony in the country. Recent updates to the property only enhance the views from the house which extend over rooftops to Smith's Cove and the harbor  Learn more...
Beacon Hill
Name: Beacon HillBedrooms: 2Bathrooms: 1SleepsMaximum: 4$1500/mo+ YR*
YEAR ROUND: A charming little house set back from the street in downtown Gloucester offers a short walk to the train station, city hall, library, restaurants, harbor and so much more.  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...
One Particular Harbor
Name: One Particular HarborBedrooms: 3Bathrooms: 2SleepsMaximum: 4year round $1250/mo + util.*
Enjoy comfort and space in this immaculate 3 bedroom, 2 full bath townhouse which is located in the heart of picturesque Rockport village, steps from her delightful shops, restaurants, galleries and harbor.  Learn more...
Rockport Village House
Name: Rockport Village HouseBedrooms: 3Bathrooms: 2.5SleepsMaximum: 8$1600/wk*
This immaculate and charming village gem offers versatility, style and convenience. A short walk to all that Rockport has to offer this 3 bedroom/ 2.5 bath home has quaint historic details, yet offers all modern conveniences and comforts with newly remode  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...
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...
Wingaersheek Summertime
Name: Wingaersheek SummertimeBedrooms: 3Bathrooms: 1.5SleepsMaximum: 6$3500/wk*
Wingaersheek Beach! This classic 50's beach house is just 75 yards to the sands of Wingaersheek's private beach. It has three bedrooms, one bath, beach shower and sleeps 6. Open concept living room with fireplace, dining room and kitchen.  Learn more...
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