Vacation Rentals in Gloucester, Massachusetts
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
Cape Ann Whale Watch
AMAZING. Seriously. Amazing. I have been on many many whale watches, and my trip this summer with Cape Ann was by far and away the BEST one I have ever...read more
Whale Watch Seven Seas Inc
Great experience! The captain/biologist on our boat kept up a non-stop interesting dialog on what we were doing, where we were going, what to look for, and...read more
Good Harbor Beach
Soft silica, lighthouse on rocky cliff backdrops and absolutely incredible surf. Good Harbor is big, deep and backed by sea oat-lined dunes. At the tail...read more
Ravenswood Park
My dog, husband and I love these trails! Anywhere dog friendly is always great.- they just require dogs to be leashed for the first ~100 yards- which is...read more
Capt Bill's Whale Watching & Deep Sea Fishing
I went on an incredible whale watch with Capt Bill's Whale Watching. The ride took just over an hour to reach whales but the crew were determined that we...read more
Schooner Thomas E Lannon
Enjoyed a lovely day on the Thomas E. Lannon Schooner yesterday! The normal daily sail is about 2 hours, and takes you out into Massachusetts Bay. The...read more
Wingaersheek Beach
I love this beach. It is especially perfect if you have little kids. When the tide is low, the beach seems to go on forever. The sand is soft and white. The...read more
Stage Fort Park & Welcoming Center
A cozy park with great views, lots of shade, extensive playground, and a small beach nested in a cove. Clean toilets and changing rooms, but this place has...read more
Hammond Castle Museum
I'm sure this "midieval castle" is beautiful in the daylight, but my experience was during a dark, cold and rainy October night. This castle has a...read more
Big Mike's Bikes
Local bike shop, family friendly, fast service with a smile. Go see Big Mike and the Cutie he shares his life and tools with. Romance on two wheels. Nread more
Cape Ann Community Cinema
Only Place around to watch something other than lame Hollywood junk! This place is great and reasonably priced. So comfortable and felt like home:)...read more
Beauport, Sleeper-McCann House
This place is a hidden gem and should be visited at least 3 times so you can get the full experience. The museum/historic mansion is jam packed with hidden...read more
Long Beach
I ended up at Long Beach when I headed to Good Harbor beach and the parking lot filled up. At the time, I wanted to head to a beach with some waves. I...read more
Coffin's Beach
I love this beach and it is my favorite beach in New England. The beach is impeccably clean because most of it is maintained by private beach associations....read more
222 Arts & Wellness Center
My boyfriend and I were referred to Lin, the massage therapist, from our innkeeper at Inn Magnolia. We were wanting to get some good R & R while away from...read more
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Early check-in & late check-out
($175)
- bedrooms 4
- community Long Beach
- rental type House
owner badge
- sleeps 10
- baths 4½
- rates (USD)
$300
- $515
/nt
$2,100 - $3,600 /wk
-
$100 off = $1,400 per week
- bedrooms 2
- community
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD)
$1,200
- $1,500
/wk
$1,500 - $3,500 /mth
- bedrooms 4
- community
- rental type Cottage
- sleeps 4
- baths 1
- rates (USD)
$1,800
- $1,800
/wk
- bedrooms 4
- community Briar Neck
- rental type House
- owner badge
- sleeps 9
- baths 2
- rates (USD)
$250
- $250
/nt
$1,100 - $3,400 /wk
- bedrooms 1
- community
- rental type Apartment
- sleeps 2
- baths 1
- rates (USD)
$500
- $700
/wk
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