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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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Gloucester things to do

 

Halibut Point State Park

I went here for the 1st time yesterday and while I expected it to be good, it turned out to be great! Its very rocky, but its still pretty easy to walk...read more

 

Good Harbor Beach

The parking was very expensive, but it was definitely worth it. At the beach, they have lots of rental items, i.e. boogie boards, sunscreen, balls. They...read more

 

Big Mike's Bikes

This shop is great enough that I make an annual pilgrimage to Gloucester to drop off my bike and hang out around town (I live 45 minutes away). Prices range...read more

 

7 Seas Whale Watch

Spot on whale watching! The boat holds about 150 people but they never pack it in. The guide was extremely knowledgeable. We went a few days ago and saw...read more

 

Wingaersheek Beach

As far as beaches go in New England, Wingaersheek is pretty solid. It's smaller than Crane and a tad smaller than Good Harbor, especially at high tide,...read more

 

Singing Beach

Dirty bathrooms..filthy beyond anything I have seen. Sand toilet paper..horrible. I guess high school kids run the place. Used to love it there. Could...read more

 

Capt. Bill & Sons Whale Watch

We had a great time even though it got a little rainy towards the end on the way back (not that they should be held responsible for the weather). It's a...read more

 

Crane Beach

This beach is consistently rated as one of the top-- if not the top-- beaches in Massachusetts each year, so naturally I had to check it out. And damn if it...read more

 

Ravenswood Park

This is a gorgeous spot for hiking, with Numerous trails, vernal pools, tall trees, and an ocean overlook. We stopped at the discovery center. They have...read more

 

Cape Ann Whale Watch

Cape Ann Whale Watch is the only whale watch we will go on! We have been on two with this company and LOVE them! Not only is everyone awesome, but they...read more

 

Hammond Castle Museum

It was my first time in a castle museum and I must say I was quite impressed with what I saw. First it is REALLY nice to walk by yourself ΒΈ, I mean not...read more

 

Rockport Music/Shalin Liu Performance Center

What a gem !!!! The most elegant venue you could imagine in a tiny sea fairing town. The acoustics are amazing. The reception hall had a gorgeous view....read more

 

Rockport Art Association

Rehearsal dinner, superplus! Open floor plan, canvases for all tastes and Big Fish-architecture that places you inside a wooden beam big top. Two major...read more

 

Schooner Thomas E Lannon

My boyfriend and I used the ever-popular Groupon deal for this schooner sail. Had a lovely sunset sail! The schooner was freshly painted and beautiful; I...read more

 

Cape Ann Community Cinema

I've gone to a good 5 or 6 movies in the last few months. A lot of them are independent films & documentaries. Most of them I would have never heard of, if...read more

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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 ($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

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

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

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
 
 
 
 
 

3 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
 
 
 
 
 

5 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

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) $1,600 - $2,000 /wk
 
 
 
 
 

32 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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Share Amazing Sunsets On Ipswich Bay With Family And Friends
Gloucester House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $400 /nt
    $2,800 /wk
 
 
 
 
 

2 reviews write a review

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
 
 
 
 
 

48 reviews write a review

*Unique Antique Stone Home* Summer rate- $2400.00/ week
Gloucester House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $343 - $385 /nt
    $2,400 /wk
 
 
 
 
 

5 reviews write a review

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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END OF SUMMER SALE Steps to Good Habor Beach, 5 bedrooms, large deck, fire pit
Gloucester House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 13
  • baths 2
  • rates (USD) $371 - $450 /nt
    $2,600 - $3,000 /wk
    $10,000 /mth
 
 
 
 
 

6 reviews write a review

Waterfront At Hodgkins Cove Inner Harbor - Spectacular Ocean Views And Sunsets!
Gloucester House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths 3
  • rates (USD) $250 - $350 /nt
    $1,250 - $2,450 /wk
    $4,000 /mth
 
 
 
 
 

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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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Atlantic Beach House - Gloucester, Massachusetts
Gloucester House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 13
  • baths 2
  • rates (USD) $3,300 /wk
 
 
 
 
 

7 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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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 - $2,000 /nt
    $14,000 /wk
    $60,000 /mth
 
 
 
 
 

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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)
 
 
 
 
 

13 reviews write a review