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Gloucester Rentals

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Gloucester Rentals

65 houses

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

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$398

1 / 23

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

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$197

1 / 20

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$150

1 / 14

Two Beaches: Immaculate single-level 3BR between Long Beach & Good Harbor

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 8

$260

1 / 27

Remodeled 3BR Gloucester Annisquam River Cottage

Gloucester cottage

3 bedrooms / 1 bathroom / Sleeps 6

$199

1 / 24

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / Sleeps 2

$165

1 / 11

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

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 5

$110

1 / 46

Beachside at Good Harbor

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 13

$432

1 / 17

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

Gloucester house

3 bedrooms / 3 bathrooms / Sleeps 8

$472

1 / 33

Waterfront Vacation House w/ Dock

Gloucester house

2 bedrooms / 2 bathrooms / Sleeps 4

$250

1 / 18

Wingaersheek beach private side 3 level treetop cottage house w/ 4 bedrooms

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$303

1 / 23

Waterfront Woodsy 3BR Cottage

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 6

$188

1 / 12

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 3

$116

1 / 26

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

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

$89

1 / 37

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / Sleeps 12

$576

1 / 18

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

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$858

1 / 17

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 10

$427

1 / 31

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

Gloucester house

1 bedroom / 1 bathroom / Sleeps 4

$61

1 / 28

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 10

$703

1 / 41

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

Gloucester cottage

7 bedrooms / 3 bathrooms / Sleeps 12

$1,060

1 / 28

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

Gloucester apartment

3 bedrooms / 2 bathrooms / Sleeps 8

$398

1 / 25

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

Gloucester house

2 bedrooms / 1 bathroom / Sleeps 4

$240

1 / 21

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

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 5

$275

1 / 28

Relax at Rocky Neck Hideaway

Gloucester townhouse

1 bedroom / 1 bathroom / Sleeps 3

$129

1 / 23

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / Sleeps 11

$504

1 / 7

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

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 10

$384

1 / 20

Close to Half Moon Bay

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 2

$125

1 / 12

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

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 10

$633

1 / 27

Helena House: European flair, close to Plum Cove Beach.

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 7

$187

1 / 21

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

Gloucester house

6 bedrooms / 5 bathrooms / Sleeps 16

$904

1 / 38

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 7

$682

1 / 23

Test Property- TA Test

Gloucester cottage

1 bedroom / 1 bathroom / Sleeps 2

$12

1 / 4

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

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 12

$384

1 / 21

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / Sleeps 12

$317

1 / 12

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / Sleeps 7

$397

1 / 19

Strawberry Cove House: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 10

$913

1 / 34

Beachmont: Easy access to Stagefort Park, Beaches & Downtown Gloucester

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 9

$419

1 / 40

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

Gloucester cottage

3 bedrooms / 1 bathroom / Sleeps 7

$480

1 / 29
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