Vacation Rentals & Houses in Gloucester

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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

$1,031

Great rentals within 20 miles that match your search

Large Furnished room for rent, quiet location

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

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Price per night from

$29

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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$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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Price per night from

$338

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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Price per night from

$304

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$516

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

Rockport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$974

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$161

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Price per night from

$184

“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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Price per night from

$167

Gap Cove at The Seaward

Rockport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$350

The Little Red House with Prize Ocean View

Rockport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$196

Modern Oceanfront Home Swampscott

Swampscott house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$700

Oceanfront Penthouse at Salisbury Beach

Salisbury condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$573

Cozy bedroom apartment in a heart of

Beverly apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$192

Downtown Beverly's hidden gem

Beverly house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$189

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

Plum Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$659

Cozy 1 Bedroom Apartment

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$458

Farmhouse

Lynn apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$189

Exclusive Lifestyle near the Ocean

Marblehead house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$916

Responds fast! avg. 1 hour 4 minutes

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$221

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$119

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$189

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$40

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$392

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$247

Luney Dunes Penthouse: 1 Dog ok, Ocean View, Deck, Spa Bath, Jetted Tub, Walk to

Newburyport hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$115

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Price per night from

$280

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$272

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$200

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$163

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Price per night from

$115

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

Swampscott house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$219

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Price per night from

$211

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Price per night from

$227

Viewing 38 of 44
rentals in Gloucester

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