Vacation Rentals & Houses in Cape Ann

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43 houses

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$281

The Little Red House with Prize Ocean View

Rockport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$196

At the Footbridge entrance to Good Harbor Beach

Gloucester house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 10

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$654

Bohemia RETREAT Studio

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$258

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

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$281

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$184

LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN

Rockport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$304

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$160

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$161

Beach & King / Beach House - 10% off April & May, 2024!

Rockport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$974

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Gorgeous in every way” The cottage is tasteful, beautiful, comfortable and convenient. The views of the wonderful working harbor are breathtaking. The sunsets, seen from the deck while relaxing, dining, drinking coffee or something else are singularly spectacular. The color scheme in the cottage, the attention to detail, the artwork - all conspire to make the entire experience of being there as relaxing and enjoyable as it could possibly be. I would recommend Summerwind Cottage to anyone. I hope to return regularly. On top of all its other charms, the owners-Hank and Linda-are delightful people that I would love to see again under any circumstances.

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$344

“An Oasis By The Sea” August 30, 2012 Dear Rose & Guy- Thank you very, very much for our wonderful stay at Periwinkle Cottage! From the beautifully decorated rooms, the most comfortable beds, soft luxurious towels and linens, convenient kitchen, TV to the lovely outdoor sitting area and garden... Omg...what a gem! It is a true delight! And the cottage is immaculate and very peaceful and tranquil. We will definitely recommend your "oasis by the sea" to our family and friends! Love, Penny and Urs Westport, Connecticut

Responds fast! avg. 1 hour 40 minutes

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$166

Gap Cove at The Seaward

Rockport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$350

Private Contemporary 2-Acre Retreat on Gloucester's Rust Island (4 Bedroom)

Gloucester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$1,031

OCEAN VIEW COTTAGE AT THE SEAWARD - EASY SEASIDE PATH TO OLD GARDEN BEACH

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$338

BEACHFRONT - Directly on Long Beach Rockport MA

Rockport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 44 minutes

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$687

Long Beach and Good Harbor Beach summer rental - Gloucester, MA

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$328

Waterfront Woodsy 3BR Cottage

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$401

Responds fast! avg. 1 hour 4 minutes

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$179

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$458

Great rentals within 20 miles that match your search

Luxurious 3 Story Beachfront Home! Newly Furnished & Captivating Views!

Plum Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$659

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$516

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$189

Oceanfront Penthouse at Salisbury Beach

Salisbury condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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$573

Responds fast! avg. 1 hour 4 minutes

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$200

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$39

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$245

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$163

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$149

Responds fast! avg. 1 hour 4 minutes

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$258

Responds fast! avg. 1 hour 4 minutes

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$237

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$98

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$211

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$205

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$174

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$306

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$227

Linden Tree: Walk to Enchanting Downtown, Spacious, Gas Fireplace, Tree Swing, G

Newburyport hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$200

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