Vacation Rentals & Houses in Gloucester

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At the Footbridge entrance to Good Harbor Beach

Gloucester house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$655

Bohemia RETREAT Studio

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$258

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$160

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

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

Gloucester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,032

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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$402

Great rentals within 20 miles that match your search

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$281

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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$339

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

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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Price per night from

$688

Large Furnished room for rent, quiet location

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

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$29

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

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$281

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

Rockport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$975

Gap Cove at The Seaward

Rockport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$350

The Little Red House with Prize Ocean View

Rockport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$196

“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. 2 hours 13 minutes

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$167

Oceanfront Penthouse at Salisbury Beach

Salisbury condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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$574

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$459

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

Plum Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$660

Exclusive Lifestyle near the Ocean

Marblehead house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$918

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$190

Modern Oceanfront Home Swampscott

Swampscott house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$701

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$184

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$161

Cozy 1 Bedroom Apartment

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$516

Farmhouse

Lynn apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$190

Responds fast! avg. 1 hour 4 minutes

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$40

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$174

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$264

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$247

SeaCity View: Stunning Views, Walk to Beach & Town, Private Garden

Swampscott house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 4 minutes

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$221

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$280

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$163

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$103

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Price per night from

$186

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Price per night from

$392

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rentals in Gloucester

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