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Cape Ann Rentals

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Cape Ann Rentals

140 rentals

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

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

$89

1 / 37

Views on High: Enjoy ocean & village views from your private roof deck.

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 5

$223

1 / 19

Rockport Seaside Retreat: Walk to waterfront, town and beaches.

Rockport house

4 bedrooms / 2 bathrooms / Sleeps 7

$267

1 / 31

Quaint Seaside Village Studio Steps From Beach

Rockport b and b

1 bedroom / 1 bathroom / Sleeps 2

$125

1 / 12

18th Century Cottage with attached guest suite

Rockport cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$185

1 / 24

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

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$300

1 / 23

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / Sleeps 12

$571

1 / 18

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$150

1 / 14

Close to Half Moon Bay

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 2

$125

1 / 12

Remodeled 3BR Gloucester Annisquam River Cottage

Gloucester cottage

3 bedrooms / 1 bathroom / Sleeps 6

$199

1 / 24

Sage Hill: Easy access to both Gloucester & Rockport

Rockport house

4 bedrooms / 3 bathrooms / Sleeps 7

$296

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 Vacation House w/ Dock

Gloucester house

2 bedrooms / 2 bathrooms / Sleeps 4

$250

1 / 18

Second Floor: 2+ Bedroom, 1.25 Bath

Manchester-by-the-Sea condo

3 bedrooms / 1 bathroom / Sleeps 5

$250

1 / 16

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 3

$115

1 / 26

Quarry Crest House: Includes swimming rights to Little Parker quarry

Rockport house

4 bedrooms / 2 bathrooms / Sleeps 10

$390

1 / 28

Strawberry Cove House: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 10

$913

1 / 34

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / Sleeps 2

$167

1 / 11

Cozy Rockport Cottage with Ocean Views

Rockport cottage

2 bedrooms / 1 bathroom / Sleeps 5

$180

1 / 14

Forever Views: You'll never want to leave your lounge chair!

Rockport house

4 bedrooms / 3 bathrooms / Sleeps 8

$953

1 / 28

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / Sleeps 6

$547

1 / 20

Captain's Cottage: Traditional setting with a private footbridge to the beach

Rockport house

2 bedrooms / 1 bathroom / Sleeps 4

$240

1 / 16

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / Sleeps 7

$397

1 / 19

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

Gloucester house

1 bedroom / 1 bathroom / Sleeps 4

$61

1 / 28

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

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 12

$384

1 / 21

The Sail Loft of Bearskin Neck

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 4

$155

1 / 15

One Bedroom Loft Apartment B at Cedar Hill Farm B & B

Essex apartment

1 bedroom / 1 bathroom / Sleeps 4

$175

1 / 6

The Robert House: 4 bedroom Rockport village house, sleeps 7

Rockport house

4 bedrooms / 1 bathroom / Sleeps 7

$378

1 / 25

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / Sleeps 4

$40

1 / 11

Captain Quarters

Rockport b and b

1 bedroom / 1 bathroom / Sleeps 2

$160

1 / 14

Pleasant House: Old-world charm w/ modern updates in the heart of the village

Rockport house

4 bedrooms / 4 bathrooms / Sleeps 10

$427

1 / 28

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

Gloucester house

2 bedrooms / 1 bathroom / Sleeps 4

$240

1 / 21

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

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$398

1 / 23

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

2 bedrooms / 1 bathroom / Sleeps 4

$182

1 / 18

Granite Courtyard: Charming cottage in Rockport with private deck and views

Rockport cottage

1 bedroom / 1 bathroom / Sleeps 4

$241

1 / 16

Popples Cove House: Private & serene waterfront setting

Rockport house

4 bedrooms / 2 bathrooms / Sleeps 7

$471

1 / 33

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

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 7

$187

1 / 21

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / Sleeps 4

“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.

$230

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