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

$654

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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Price per night from

$344

Test Property- TA Test

Gloucester cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$14

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

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

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

$687

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

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

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Price per night from

$281

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

$974

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Price per night from

$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

$166

The Harborfront, Beverly/Salem, Boston North Shore

Beverly apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$516

Gap Cove at The Seaward

Rockport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$350

Modern Oceanfront Home Swampscott

Swampscott house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$700

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

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

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

Beach Front Luxe: Italian vibes & coastal glam in Rockport!

Rockport house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$745

Crow Haven Corner Presents Lorelei's Witch House

Salem house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$659

NEW! Family-Friendly Getaway < 1 Mi to Dtwn Salem!

Salem apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$687

Cozy 1 Bedroom Apartment

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Sunshine House steps from Beach

Seabrook house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$802

ROCKPORT MA OLD GARDEN BEACH RENTAL !

Rockport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$458

Big New England Family Home; walk to beach, shops

Rockport house

  • 9 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$1,031

Salisbury Coastal Retreat

Salisbury studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$195

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

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$219

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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Price per night from

$221

Responds fast! avg. 1 hour 4 minutes

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Price per night from

$164

Viewing 38 of 58
rentals in Gloucester

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