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At the Footbridge entrance to Good Harbor Beach
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$652
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$149
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$137
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
Gloucester house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$118
Romantic SUMMERWIND COTTAGE- Scenic Harbor View
Gloucester cottage
2 bedrooms / 1 bathroom / sleeps 4
“Romantic Summerwind Cottage lives up to its name” We thoroughly enjoyed our stay in "Summerwind". It is a truly beautiful house. Linda and Hank, you did a wonderful job in remodeling and decorating the place. The color scheme and artwork reflect the lovely area and the lifestyle of Gloucester and we truly enjoyed the ambiance here. We felt very comfortable and welcomed in the house which was spotlessly clean and furnished with everything one could possibly need for their stay. We loved the area of East Gloucester. Good Harbor beach was a very enjoyable walk from the house. Rocky Neck and the Eastern Point Lighthouse were also very near and Rockport is only a short drive away. Our favorite restaurants were "My place by the Sea" in Rockport, "7th Wave " also in Rockport and "The Rudder" in Rocky Neck. We also enjoyed the beer at the Cape ann Brewing Company in Gloucester. And best of all was a barbecue on our veranda overlooking the Gloucester harbor. This was also where we enjoyed breakfast each morning watching the activity below. Linda, your exceptional taste and attention to detail made us choose Summerwind Cottage and we were not disappointed - it surpassed our expectations. A big thank you from Mira, Dominic and family (Ireland).
Responds fast! avg. 29 minutes
Price per night from
$321
Price per night from
$14
Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)
Gloucester house
4 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$1,031
Responds fast! avg. 29 minutes
Price per night from
$257
Long Beach and Good Harbor Beach summer rental - Gloucester, MA
Gloucester house
3 bedrooms / 1 bathroom / sleeps 6
Price per night from
$327
Price per night from
$401
Great rentals within 20 miles that match your search
Price per night from
$946
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet
Rockport cottage
1 bedroom / 1 bathroom / sleeps 2
“An Oasis By The Sea” August 30, 2012 Dear Rose & Guy- Thank you very, very much for our wonderful stay at Periwinkle Cottage! From the beautifully decorated rooms, the most comfortable beds, soft luxurious towels and linens, convenient kitchen, TV to the lovely outdoor sitting area and garden... Omg...what a gem! It is a true delight! And the cottage is immaculate and very peaceful and tranquil. We will definitely recommend your "oasis by the sea" to our family and friends! Love, Penny and Urs Westport, Connecticut
Responds fast! avg. 20 minutes
Price per night from
$194
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$685
Price per night from
$29
GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
Rockport cottage
2 bedrooms / 1 bathroom / sleeps 2
Responds fast! avg. 3 hours 17 minutes
Price per night from
$280
GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
Rockport apartment
2 bedrooms / 1 bathroom / sleeps 3
Responds fast! avg. 3 hours 17 minutes
Price per night from
$280
OCEAN VIEW COTTAGE AT THE SEAWARD - EASY SEASIDE PATH TO OLD GARDEN BEACH
Rockport cottage
2 bedrooms / 1 bathroom / sleeps 4
Responds fast! avg. 3 hours 17 minutes
Price per night from
$337
LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN
Rockport apartment
1 bedroom / 1 bathroom / sleeps 2
Responds fast! avg. 3 hours 17 minutes
Price per night from
$303
Price per night from
$195
Luxurious 3 Story Beachfront Home! Newly Furnished & Captivating Views!
Plum Island house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$656
Responds fast! avg. 3 hours 17 minutes
Price per night from
$348
Ocean Front Retreat Nine Miles to Boston / Logan Airport
Lynn house
1 bedroom / 1 bathroom / sleeps 2
Price per night from
$387
Price per night from
$191
Price per night from
$189
Beach Front Luxe: Italian vibes & coastal glam in Rockport!
Rockport house
5 bedrooms / 2 bathrooms / sleeps 12
Responds fast! avg. 2 hours 14 minutes
Price per night from
$742
Bearskin Neck - Fabulous water views from this private second floor condo!
Rockport condo
1 bedroom / 1 bathroom / sleeps 2
Price per night from
$80
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$458
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$916
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$659
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$172
Price per night from
$315
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$287
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$516
NEW! Family-Friendly Getaway < 1 Mi to Dtwn Salem!
Salem apartment
3 bedrooms / 2 bathrooms / sleeps 12
Price per night from
$344
Price per night from
$458
Viewing 38 of 61
rentals in Gloucester
About Gloucester
Located on the northern shores of Massachusetts, the town of Gloucester is a vacation paradise that generations of travelers return to every year. The winding streets of this historic town are lined with quaint shops, interesting museums, charming cafes, and unforgettable seafood restaurants. Come here to experience the beautiful rocky coastlines and soft sand beaches of Massachusetts. Hike the trails and stop at breathtaking overlooks with views of the Atlantic Ocean. Visit historic homes and lighthouses. Spend the afternoon swimming, snorkeling, or relaxing on a pristine beach. And then go home at night to your own private vacation rental and host dinner for your family and friends. Many vacation rentals in Gloucester are less expensive than hotels and offer more space and better amenities. Wake up in the morning and watch the sun rise from the deck of your beach condo or summer house, then head downtown to spend the day exploring and making fun vacation memories.
Here are a few additional suggestions for your trip:
- Take a brewery tour: Gloucester is the traditional home of several long established breweries and craft distilleries. Taste some of the area's award winning artisanal spirits.
- Tour Hammond Castle: This extraordinary structure was once the home of John Hays Jr., a wealthy eccentric who amassed an extensive collection of medieval artifacts.
- Visit the Fisherman's Memorial Monument: This fascinating memorial was built in 1925 to honor all the fishermen who have been lost at sea since the 17th century.
- Play on the beach: Swim, build a sandcastle, or just relax on Good Harbor Beach or Stage Fort Park and Beach, two of the most popular beach destinations in the area.
- Visit the Rocky Neck Art Colony: This is the oldest established colony for artists in the United States and has been a destination for art lovers since the 1840s.
- Visit the Beauport Museum or the Cape Ann Historical Museum: Learn more about the fascinating history of Cape Ann with the changing exhibits of these popular museums.
Gloucester offers an ideal scenic back drop for whatever vacation activities you have in mind. The best way to enjoy it all is with a stay in your own apartment rental or summer condo. Find a luxury vacation rental just a few steps from the beach that offers all the amenities you and your family need. While you're visiting Gloucester, be sure to plan day trips to coastal destinations nearby like Cape Cod and Plymouth.
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