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Gloucester and Annisquam Vacation Home Rentals(84)

84 Results
$300 - $330
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(40)
  • 7 BR,
  • 3 BA,
  • Sleeps 16
4 - 7 night minimum stay
(18)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 7 night minimum stay
(5)
  • 6 BR,
  • 3 BA,
  • Sleeps 15
2 - 7 night minimum stay
(5)
  • 5 BR,
  • 3 BA,
  • Sleeps 14
2 - 7 night minimum stay
$140 - $250
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 7 night minimum stay
2 Reviews
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
2 Reviews
$50 - $200
per night
1 - 31 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
1 - 31 night minimum stay
(6)
  • 4 BR,
  • 1 BA,
  • Sleeps 7
7 night minimum stay
(4)
$429 - $450
per night
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 13
2 - 7 night minimum stay
(9)
$1,400 - $2,000
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(20)
$150 - $414
per night
2 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 14 night minimum stay
$373 - $1,900
per week
7 - 30 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night minimum stay
$2,400 - $3,250
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 11
7 night minimum stay
(9)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night minimum stay
2 Reviews
  • 5 BR,
  • 3 BA,
  • Sleeps 10
2 - 90 night minimum stay
(5)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
$125 - $150
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
2 - 7 night minimum stay
(6)
$385
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night minimum stay
(7)
$321 - $650
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(6)
$1,200 - $1,800
per week
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(5)
$1,500 - $2,000
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 7
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 7 night minimum stay
1 Review
$214 - $457
per night
5 - 7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 7 night minimum stay
(6)
$500 - $550
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
$5,075
per week
14 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
14 night minimum stay
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Recent Gloucester and Annisquam Reviews

A rich and genuine Cape Ann experience

5 of 5
We were immediately comfortable and relaxed in Jock's family home, which felt little-changed from how it must have been when he grew up there. With obvious pride, he generously provided a fun and informative tour of the property, steeped in significant family history. The house is spacious and open with lots of light, simply but warmly furnished with wicker and lots of nautical and sea-themed art. The kitchen is huge and has everything one could need and more. We cooked lobster several times! We loved having our two Newfies with us and taking long walks each morning up the hill, along the path overlooking Hodgkin's cove, down to the beaches, and winding back up through the woods, all without leaving the property! This was a perfect relaxing vacation, keeping it simple while having it all. Thank you Jock.
  • Submitted: Oct 16, 2014
  • Stayed: Oct 2014

Fall Weekend/Wedding

5 of 5
We all had a wonderful weekend and found the home to be spotless clean and the beds were very comfortable. I highly recommend a stay at this home. We were greeted by PJ and told to contact him with any issues (which there were none ). Thanks for allowing us to enjoy your home.
  • Submitted: Oct 9, 2014
  • Stayed: Oct 2014

Great Vacation Home and Location

5 of 5
Liz, we want to thank you for sharing your home with us. Everything was perfect. The walk to the beach was pleasant and our puppy loved playing in the ocean with the other dogs. We enjoyed our time at your home. It is especially nice you allowed us to bring Bella along so she did not need to stay at home! You have your home so clean and everything you supplied was great.......we couldn't ask for a better place to stay. We had a great trip on the Cape Ann Whale Watch. We hope to come back to visit again.
  • Submitted: Sep 24, 2014
  • Stayed: Sep 2014