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Vacation Rentals & Houses in Gloucester

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61 houses

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$652

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$149

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$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

Test Property- TA Test

Gloucester cottage

1 bedroom / 1 bathroom / sleeps 2

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

Stunning SUNSET STUDIO w/Scenic Harbor View

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

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

Waterfront Woodsy 3BR Cottage

Gloucester house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$401

Great rentals within 20 miles that match your search

Beach & King Street Inn / Beach House Rental

Rockport house

6 bedrooms / 5 bathrooms / sleeps 14

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

Directly on Long Beach Rockport MA

Rockport house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$685

Large Furnished room for rent, quiet location

Lynn apartment

1 bedroom / 1 bathroom / sleeps 1

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

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

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

Gap Cove at The Seaward

Rockport apartment

2 bedrooms / 2 bathrooms / sleeps 4

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

Rockwood lodge

Rockport cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$451

Cozy bedroom apartment in a heart of

Beverly apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$191

Downtown Beverly's hidden gem

Beverly house

1 bedroom / 1 bathroom / sleeps 4

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

Oceanfront Penthouse w/Friends & Family

Salisbury condo

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$458

Exclusive Lifestyle near the Ocean

Marblehead house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$916

Crow Haven Corner Presents Lorelei's Witch House

Salem house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$659

Salem 3rd floor 3BR Near Historical District

Salem apartment

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$172

Salem 2nd Floor 4BR Near Historical District

Salem apartment

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$315

Salem 1st Floor 4BR Near Historical District

Salem apartment

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$287

Ocean Front Cottage on Scenic Long Beach

Rockport cottage

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$516

Back Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$492

The Forsythia Apt

Salem apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$201

NEW! Family-Friendly Getaway < 1 Mi to Dtwn Salem!

Salem apartment

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$344

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$458

Viewing 38 of 61
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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