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Vacation Rentals in Gloucester, Massachusetts

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about Gloucester

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Gloucester, Massachusetts vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Gloucester are added and updated every week!

Compared to hotels, Gloucester vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Gloucester, Massachusetts Vacation Rentals and Tourism

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

DEAL!! Steps to Beautiful Long Beach
Gloucester House Rental Picture
  • House Rental Deals and Specials Early check-in & late check-out ($190)
  • bedrooms 4
  • community Long Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $325 - $520 /nt
    $2,275 - $3,650 /wk
 
 
 
 
 

7 reviews write a review

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) $250 /nt
    $1,100 - $3,400 /wk
 
 
 
 
 

8 reviews write a review

Rocky Neck Studio Apartment
Gloucester Apartment Rental Picture
  • bedrooms 1
  • community Rocky Neck
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $500 - $700 /wk
 
 
 
 
 

9 reviews write a review

Classic New England Oceanfront
Gloucester House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $3,500 /wk
 
 
 
 
 

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A Sunset Serenade - Delightful Studio with Deck Overlooking Scenic Harbor
Gloucester Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $900 - $1,000 /wk
 
 
 
 
 

46 reviews write a review

Treehouse-Like Condo W/ Views Of Ocean, Boulevard And Fisherman's Statue
Gloucester House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $1,470 /wk
 
 
 
 
 

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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
Gloucester House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $700 /nt
    $2,500 - $4,900 /wk
 
 
 
 
 

2 reviews write a review

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam
Gloucester House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 15
  • baths 3
  • rates (USD) $700 - $750 /nt
    $2,500 - $5,100 /wk
 
 
 
 
 

4 reviews write a review

Buoy 23: Direct waterfront cottage with deepwater dock on the Annisquam River
Gloucester Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $285 - $428 /nt
    $1,500 - $2,995 /wk
    $6,200 - $12,000 /mth
 
 
 
 
 

18 reviews write a review

Breathtaking views from modern ocean front apt. steps from Good Harbor Beach
Gloucester Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

11 reviews write a review

Steps to Good Habor Beach, 5 bedrooms, large deck and outdoor shower, fire pit.
Gloucester House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 13
  • baths 2
  • rates (USD) $400 - $450 /nt
    $2,800 - $3,000 /wk
    $10,000 /mth
 
 
 
 
 

1 reviews write a review

Overlooking Good Harbor Beach In A Bright Spacious Family Home
Gloucester House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $500 - $550 /nt
    $3,450 - $3,500 /wk
    $13,500 - $13,800 /mth
 
 
 
 
 

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Romantic SUMMERWIND COTTAGE - Scenic Harbor View w/Large Deck
Gloucester House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $1,500 - $1,800 /wk
 
 
 
 
 

29 reviews write a review

Spectacular Setting In The Dunes. Private Beach, Sunset And Sunrises Over Water.
Gloucester Villa Rental Picture
  • bedrooms 5
  • rental type Villa
  • sleeps 14
  • baths 7
  • rates (USD) $1,500 - $1,714 /nt
    $12,000 /wk
    $50,000 /mth
 
 
 
 
 

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Wingaersheek Beachfront. FULLY BOOKED for 2014.
Gloucester House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $725 /nt
 
 
 
 
 

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