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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Price per night from

$258

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$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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$345

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

$1,033

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

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$328

Waterfront Woodsy 3BR Cottage

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$401

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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Price per night from

$281

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Price per night from

$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

$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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Price per night from

$304

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

Rockport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$975

“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

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

$689

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

$197

Oceanfront Penthouse at Salisbury Beach

Salisbury condo

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$574

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$459

Exclusive Lifestyle near the Ocean

Marblehead house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$916

Hillside Ocean View 2BR with Private Beach Access

Ipswich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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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

$658

Modern Oceanfront Home Swampscott

Swampscott house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$700

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$515

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$161

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Price per night from

$184

Farmhouse

Lynn apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$189

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$221

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Price per night from

$249

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$234

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

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$271

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

Newburyport hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$156

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$224

Responds fast! avg. 1 hour 4 minutes

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$164

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$187

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$179

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Price per night from

$299

Viewing 38 of 48
rentals in Gloucester

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