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186 houses
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$471
Golden Sands at Good Harbor: Across the street from the beach
Gloucester cottage
7 bedrooms / 3 bathrooms / sleeps 12
Price per night from
$1,284
Lovely 'Blue Heron Cottage' on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 6
Responds fast! avg. 4 minutes
Price per night from
$237
Price per night from
$364
At the Footbridge entrance to Good Harbor Beach
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$663
Price per night from
$134
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$717
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach
Gloucester house
5 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$1,109
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester apartment
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$280
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$1,035
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 7
Price per night from
$478
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$757
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$792
Price per night from
$146
Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 0 minutes
Price per night from
$197
Responds fast! avg. 21 minutes
Price per night from
$128
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$614
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$688
Price per night from
$1,351
Price per night from
$198
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester house
2 bedrooms / 1 bathroom / sleeps 6
Price per night from
$373
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$1,164
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
Gloucester house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$127
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$759
Bell View: Private tennis court and an in-law suite.
Gloucester house
6 bedrooms / 5 bathrooms / sleeps 16
Price per night from
$1,431
Romantic SUMMERWIND COTTAGE- Scenic Harbor View
Gloucester cottage
2 bedrooms / 1 bathroom / sleeps 6
“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).
Price per night from
$180
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$698
Price per night from
$592
High Rock Cottage: Astounding views from every angle!
Gloucester house
6 bedrooms / 4 bathrooms / sleeps 10
Price per night from
$1,229
Price per night from
$150
Price per night from
$189
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 9
Price per night from
$554
Price per night from
$14
Plaisance - a summer vacation rental near Bass Rocks
Gloucester house
3 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$648
Cedar Ledge Annisquam: Ocean views & traditional New England charm.
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 14
Price per night from
$1,399
Charming cottage near the ocean w/beach access & near Gloucester!
Gloucester cottage
2 bedrooms / 1 bathroom / sleeps 6
Responds fast! avg. 0 minutes
Price per night from
$192
Viewing 38 of 186
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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