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136 houses
Golden Sands at Good Harbor: Across the street from the beach
Gloucester cottage
7 bedrooms / 3 bathrooms / sleeps 12
Price per night from
$1,513
At the Footbridge entrance to Good Harbor Beach
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$663
Lovely 'Blue Heron Cottage' on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 6
Responds fast! avg. 1 hour 8 minutes
Price per night from
$187
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
$1,436
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$895
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$1,262
Price per night from
$132
Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$896
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 7
Price per night from
$543
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$896
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
$360
Price per night from
$1,344
Price per night from
$121
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester house
2 bedrooms / 1 bathroom / sleeps 6
Price per night from
$442
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
$764
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
Gloucester house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$129
Bell View: Private tennis court and an in-law suite.
Gloucester house
6 bedrooms / 5 bathrooms / sleeps 16
Price per night from
$1,216
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$696
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).
Responds fast! avg. 18 minutes
Price per night from
$299
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$867
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
$747
Price per night from
$595
Price per night from
$16
Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)
Gloucester house
4 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$1,051
Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.
Gloucester house
4 bedrooms / 3 bathrooms / sleeps 10
Price per night from
$1,020
Cedar Ledge Annisquam: Ocean views & traditional New England charm.
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 14
Price per night from
$1,286
Helena House: European flair, close to Plum Cove Beach.
Gloucester house
3 bedrooms / 1 bathroom / sleeps 7
Price per night from
$483
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Gloucester apartment
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$441
Beach Walk: Good Harbor Beach footbridge just steps away!
Gloucester apartment
1 bedroom / 1 bathroom / sleeps 3
Price per night from
$308
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$714
Plaisance - a summer vacation rental near Bass Rocks
Gloucester house
3 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$777
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 9
Price per night from
$639
Responds fast! avg. 18 minutes
Price per night from
$161
Chester Square: Waterfront home in historic Annisquam Village.
Gloucester house
4 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$1,202
The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$705
Viewing 38 of 136
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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