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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

Best waves crashing on the shore I have seen so far in Massachussets. Very calming & peaceful. Not a lot to do but that's what I was looking for. With the...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

Went on a whale watch on 7-11-14 and we couldn't have had better weather. This was a first time experience for me and I have to say it was more than...read more

 

Wingaersheek Beach

+peculiarly soft sand +lots of space +snack shop is remarkably good, and economical +no greenheads (regional hazard) -very far from Boston, especially with...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

 

Singing Beach

The closest thing to a California beach in Massachusetts. I live in Toronto, Canada, where it's not exactly possible to take a walk on the ocean. I was in...read more

 

Crane Beach

the whitest softest baby powder sand! Visitors flock from across the country to bask on this beautiful beach. NOTE: leave before sunset ... to avoid the...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

I went on the 830 boat last Saturday. It was pretty crowded but not jammed. There were still seats and room to move around. I liked how they offered real...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

 

Beauport, Sleeper-McCann House

This place was really neat and I basically ended up there randomly when I was poking around in the area. I managed to show up just as a tour was starting,...read more

 

Schooner Thomas E Lannon

Came on a groupon and made friends, and found zen. BEAUTIFUL slow cruise of the harbor, relaxing and full of maritime stories. Family owned business -...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

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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 - $529 /nt
    $2,275 - $3,700 /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
 
 
 
 
 

5 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

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

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

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

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

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) $2,000 /nt
    $14,000 /wk
    $60,000 /mth
 
 
 
 
 

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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
 
 
 
 
 

1 reviews write a review

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) $429 - $450 /nt
    $2,000 - $3,000 /wk
    $10,000 /mth
 
 
 
 
 

6 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
 
 
 
 
 

33 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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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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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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