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Vacation Rentals in Gloucester, Massachusetts

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about Gloucester

We feature rental homes, villas, cabins, cottages, and condos in destinations all over the world. If you're looking for Gloucester, Massachusetts vacation rentals, click the "rental results" tab and inquire about your favorite listings. Browse Gloucester vacation deals, family-friendly amenities, and more. If you can't find what you're looking for, remember that vacation rentals in Gloucester, Massachusetts are added and updated every week, so please bookmark us and come back for a visit! Feel free to peruse other destinations as well, as we've got everything from large family vacation rentals to lake cabins to luxury beach houses.

Gloucester, Massachusetts Vacation Rentals and Tourism

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DEAL!! Steps to Beautiful Long Beach
Gloucester House Rental Picture
  • House Rental Deals and Specials Early check-in & late check-out ($175)
  • bedrooms 4
  • community Long Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $300 - $515 /nt
    $2,100 - $3,600 /wk
 
 
 
 
 

6 reviews write a review

Beautiful Colonial House. Great Quiet Location
Gloucester House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 12
  • baths 2
  • rates (USD) $2,000 - $2,000 /wk
 
 
 
 
 

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Stunning views, wall-to-wall windows, 4BR oceanfront
Gloucester House Rental Picture
  • bedrooms 4
  • community Briar Neck
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths 2
  • rates (USD) $1,100 - $3,300 /wk
 
 
 
 
 

5 reviews write a review

Restored Victorian with View of Ocean
Gloucester House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,385 - $1,385 /wk
 
 
 
 
 

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Rocky Neck Studio Apartment
Gloucester Apartment Rental Picture
  • bedrooms 1
  • community
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $500 - $600 /wk
 
 
 
 
 

4 reviews write a review

Gorgeous 2br Oceanfront Condo
Gloucester Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $900 - $900 /wk
    $1,500 - $1,500 /mth
 
 
 
 
 

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200 Year Old Converted Barn Near the Ocean
Gloucester Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • sleeps 3
  • baths 1
  • rates (USD) $1,000 - $1,500 /wk
 
 
 
 
 

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Wrap around porch overlooking private beach and lighthouse
Gloucester House Rental Picture
  • bedrooms 3
  • community Annisquam
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $3,500 - $5,000 /wk
    $10,000 - $17,000 /mth
 
 
 
 
 

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Beautiful Ocean Front House: upper or lower level listing
Gloucester House Rental Picture
  • bedrooms 3
  • community Eastern Point
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $3,000 - $3,500 /wk
    $11,000 - $12,000 /mth
 
 
 
 
 

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Beautiful 6 Bedroom Ocean Front Home
Gloucester House Rental Picture
  • bedrooms 6
  • community Eastern Point
  • rental type House
  • sleeps 20
  • baths
  • rates (USD) $5,500 - $5,500 /wk
    $18,000 - $18,000 /mth
 
 
 
 
 

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