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Vacation Rentals & Houses in Gloucester

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Vacation Rentals & Houses in Gloucester

About Gloucester

199 houses

Captain John Stephens House: Sparkling new studio in the heart of Gloucester

Gloucester studio

Studio / 1 bathroom / sleeps 2

1 / 24

Little Red House: Close to Gloucester's historic Stage Fort Park & beaches

Gloucester house

3 bedrooms / 1 bathroom / sleeps 5

1 / 19

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / sleeps 2

1 / 11

Long Beach House: Large, comfortable home just 285 feet from the white sands!

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

1 / 20

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

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 7

1 / 29

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 25 minutes

1 / 37

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

Gloucester house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 25 minutes

1 / 28

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 16 minutes

1 / 26

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 12

1 / 18

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

1 / 31

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

1 / 14

Beachside at Good Harbor

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 13

1 / 17

Diamond in the Sky: Upscale townhouse near Good Harbor Beach.

Gloucester condo

3 bedrooms / 3 bathrooms / sleeps 7

1 / 35

Cool Cove: Wingaersheek Beach plus your own private beach & all those views!

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

1 / 21

Walk to Beach - Modern Apartment

Gloucester house

1 bedroom / 1 bathroom / sleeps 2

1 / 18

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

1 / 9

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

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

1 / 21

Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

1 / 17

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

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

1 / 33

Stunning Views - Spacious Home

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

1 / 39

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 8

1 / 27

Fabulous Waterfront 2 Bedroom - Boat dock option

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

1 / 7

Waterfront Vacation House w/ Dock

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 33 minutes

1 / 18

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

1 / 20

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

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

1 / 28

NEW! STUNNING STUDIO w/Scenic Harbor View

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 49 minutes

1 / 25

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 46 minutes

1 / 12

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 6

1 / 37

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

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 6

1 / 33

Welcome Home: Walk to Gloucester's historic harbor and beaches.

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 12

1 / 31

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 49 minutes

1 / 27

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / sleeps 7

1 / 19

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

1 / 23

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 11 minutes

1 / 7

Bell View: Private tennis court and an in-law suite.

Gloucester house

6 bedrooms / 5 bathrooms / sleeps 16

1 / 54

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

1 / 26

Relax at Rocky Neck Hideaway

Gloucester townhouse

1 bedroom / 1 bathroom / sleeps 3

1 / 23

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

Gloucester house

3 bedrooms / 1 bathroom / sleeps 6

1 / 11
Viewing 38 of 199

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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