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Houses Cape Ann

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75 houses

Rockwood Cottage

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$430

Booth Cottage: Walk down a private path to fabled Singing Beach.

Manchester-by-the-Sea house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$885

NEW! Dreamy Rockport Getaway < Half Mile to Coast!

Rockport house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 29 minutes

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Price per night from

$232

Classic Victorian home with views of the ocean and twin light houses.

Rockport house

7 bedrooms / 2 bathrooms / sleeps 14

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Price per night from

$1,298

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$843

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

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$912

River's Edge: A charming 2BR riverfront home in Gloucester.

Gloucester house

3 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$259

The Cottage

Manchester-by-the-Sea house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 11 minutes

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Price per night from

$450

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

Gloucester house

6 bedrooms / 5 bathrooms / sleeps 16

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Price per night from

$1,785

Magnolia Tides: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$767

Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach

Gloucester house

5 bedrooms / 3 bathrooms / sleeps 9

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Price per night from

$1,685

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

Gloucester house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$519

Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$855

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

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$724

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

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,107

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

Rockport house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$898

River Watch: Waterfront rental home with views and private dock.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$642

Directly on Long Beach Rockport MA

Rockport house

4 bedrooms / 3 bathrooms / sleeps 14

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Price per night from

$679

Chester Square: Waterfront home in historic Annisquam Village.

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,468

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 8

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Price per night from

$694

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

Gloucester house

3 bedrooms / 1 bathroom / sleeps 7

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Price per night from

$589

Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean

Rockport house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$730

Sage Hill: Easy access to both Gloucester & Rockport

Rockport house

4 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$800

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$1,554

Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$1,077

Beach & King Street Inn / Beach House Rental

Rockport house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$950

Straitsmouth Cove: Outstanding ocean views at Gap Head Cove in Rockport.

Rockport house

5 bedrooms / 2 bathrooms / sleeps 9

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Price per night from

$1,515

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

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$498

The Lady Bug House

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$640

The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$837

Captain John Butman House: Charming historic home in the village of Rockport.

Rockport house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$567

Back Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$492

Beautiful oceanfront home with sweeping water views and private beach.

Rockport house

6 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$2,568

Family Tides: Only a half-mile from Good Harbor Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$1,035

Historic meets contemporary at Pigeon Hill

Rockport house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$601

Four Winds: A serene escape close to picturesque Rockport village.

Rockport house

3 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$637

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$890

Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.

Gloucester house

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$556

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