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Gloucester and Annisquam Vacation Home Rentals(84)

84 Results
  • 7 BR,
  • 3 BA,
  • Sleeps 16
4 - 7 night minimum stay
(18)
$300 - $330
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(40)
  • 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)
  • 6 BR,
  • 3 BA,
  • Sleeps 15
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
$410 - $450
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(3)
$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)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
$3,500
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
$429 - $450
per night
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 13
2 - 7 night minimum stay
(9)
$150 - $414
per night
2 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 14 night minimum stay
$1,400 - $2,000
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(20)
$373 - $1,900
per week
7 - 30 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
2 - 90 night minimum stay
(5)
$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,
  • 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)
$1,200 - $1,800
per week
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(6)
  • 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)
$1,500 - $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
$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
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(5)
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Recent Gloucester and Annisquam Reviews

Thanksgiving at Serenity at Folly Point

5 of 5
We spent last weekend at this spectacular home in Gloucester and I am happy to provide a review sharing our experience. We had 9 people in our group; made up of two Canadian families that spend every Thanksgiving weekend together. This house was the perfect spot for us to enjoy our holiday. The layout of the house provides many different common areas for people to spread out and it included everything we could have hoped for. After traveling 13 hours to get there, a soak in the fabulous hot tub was a welcome treat. We arrived to a bottle of wine provided by our host and plenty of information about things to do around the area. The grounds of the house were incredible; our kids had a blast playing in the yard and enjoying the hammock as well as the games that were on site (the Wii and the board games). With regards to cost, we had priced out a very reasonable hotel in Boston for the same weekend. It was cheaper for us to rent the house for 3 nights than it was to rent 3 hotel rooms for two nights so fantastic value for your money. And the best part was being able to cook a large family dinner and still honour our traditions. Thank you to Kathy for all her help in booking this property. We felt pampered and cared for from the moment we inquired about renting the property until we returned home. We will definitely be back. This is an excellent alternative to the hustle and bustle of Boston. Transportation into Boston and back was cheap and incredibly easy so we didn't miss out on anything. Salem this time of year is must as well. Call Kathy. She will take care of you. The Jones Family
  • Submitted: Oct 16, 2014
  • Stayed: Oct 2014

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