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Vacation Rentals & Houses in Gloucester

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Vacation Rentals & Houses in Gloucester

About Gloucester

211 houses

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

1 / 37

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$275

1 / 14

Lovely 'Blue Heron Cottage' on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$199

1 / 24

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / sleeps 2

Price per night from

$165

1 / 11

Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 13 minutes

Price per night from

$110

1 / 46

Inviting apartment with harbor views, fireplace, patio, & gas grill!

Gloucester house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$84

1 / 28

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 8 minutes

Price per night from

$500

1 / 7

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$115

1 / 26

Stunning Views - Spacious Home

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$500

1 / 39

Surf's Up, an unexpected treasure in the heart of downtown Gloucester.

Gloucester apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$290

1 / 21

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$240

1 / 21

Long Beach Place: Just steps from the white sand & surf.

Gloucester apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$390

1 / 25

Beachside at Good Harbor

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 13

Price per night from

$429

1 / 17

Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$325

1 / 26

Close to Half Moon Bay

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$125

1 / 12

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

$197

1 / 20

Waterfront Vacation House w/ Dock

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 40 minutes

Price per night from

$300

1 / 18

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$571

1 / 18

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$419

1 / 31

Fabulous Waterfront 2 Bedroom - Boat dock option

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$67

1 / 7

Golden Sands at Good Harbor: Across the street from the beach

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$1,010

1 / 28

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$650

1 / 23

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$283

1 / 27

Salt Island Views: Walking distance to Good Harbor & Long Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$490

1 / 19

Seaside House: Good Harbor Beach and the Back Shore right outside

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$633

1 / 25

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$530

1 / 37

Waterfront Woodsy 3BR Cottage

Gloucester house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 13 minutes

Price per night from

$186

1 / 12

Good Harbor Escape: Swim or walk over to Good Harbor Beach!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$350

1 / 11

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

Responds fast! avg. 2 hours 37 minutes

Price per night from

$240

1 / 26

Sea Fox: Custom-designed home with rights to private Coffins Beach

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$390

1 / 23

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$690

1 / 40

Beach Walk: Good Harbor Beach footbridge just steps away!

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$238

1 / 11

Stage Fort Park Place

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 14

Price per night from

$269

1 / 11

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$304

1 / 29

Quiet cottage near beach

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 19 minutes

Price per night from

$170

1 / 5

Water's Edge: Direct waterfront on picturesque Goose Cove with dock

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$450

1 / 33

Rosemarc House: 180-degree ocean views & a private beach

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,433

1 / 33

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$397

1 / 19
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About Gloucester

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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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