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Vacation Rentals & Houses in Gloucester

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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

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / sleeps 12

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

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

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

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / sleeps 2

Price per night from

$192

Close to Half Moon Bay

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

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

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

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

Magnolia Tides: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,351

Quiet cottage near beach

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

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

Rockwood Cottage

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$435

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 8

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

Relax at Rocky Neck Hideaway

Gloucester townhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$150

Good Harbor Beach House - Walk to Shops

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 7

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

Test Property- TA Test

Gloucester cottage

1 bedroom / 1 bathroom / sleeps 2

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

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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.

Top Destination reviews

Romantic SUMMERWIND COTTAGE- Scenic Harbor View
A Perfect Gloucester Setting

My wife and I stayed a week at Summerwind in September. The house overlooks Gloucester harbor, and although close to the center of town and near restaurants and shops, it is situated on a hillside off a quiet side street. The cottage itself is airy and beautifully furnished with an attractive color scheme, and some paintings. it is not cluttered with bricabrak and other cutsey things one might find in a rental. I have built a few of the houses I have lived in and can say that the structure, workmanship, and finishing of Summerwind is exceptional. The kitchen and bath are fully fitted out and all the fixtures are new. Kitchen needs, like paper towels, spices, and condiments were well present. Mattresses are of good quality and there is plenty of bed linens, blankets, and towels.The ample deck is a great place for sunsets and evening dining. Linda amero is a charming and helpful landlady - without being intrusive. She lives next door, and let us know right off she was always available to help with finding supermarkets and places of interest. There is a printed sheet of instructions that made our stay easy. There is also Wifi and a large screen TV with cable. We would give it ten stars if we could. I know we will be back to Gloucester and Summerwind. Frank O'Brien Roanoke, Virginiasee more

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