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Gloucester and Annisquam House Rentals(84)

84 Results
  • 6 BR,
  • 2 BA,
  • Sleeps 11
2 night min stay
(17)
$300
per night
4 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night min stay
(42)
  • 5 BR,
  • 2 BA,
  • Sleeps 12
2 - 7 night min stay
(4)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
(7)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 7 night min stay
(5)
  • 6 BR,
  • 3 BA,
  • Sleeps 15
2 - 7 night min stay
(5)
  • 7 BR,
  • 3 BA,
  • Sleeps 16
4 - 7 night min stay
(22)
  • 6 BR,
  • 3 BA,
  • Sleeps 15
2 - 7 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
7 night min stay
$200 - $250
per night
3 - 4 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 4 night min stay
$140 - $250
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 7 night min stay
(6)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
4 - 7 night min stay
(3)
  • 4 BR,
  • 1 BA,
  • Sleeps 8
7 night min stay
(5)
$1,400 - $2,100
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night min stay
(21)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
2 - 7 night min stay
(6)
$2,450 - $3,250
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 11
7 night min stay
(9)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night min stay
2 Reviews
$500 - $550
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 14 night min stay
$373 - $1,900
per week
7 - 30 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night min stay
1 Review
$429 - $450
per night
2 - 7 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 13
2 - 7 night min stay
(9)
$357 - $385
per night
3 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(6)
  • 3 BR,
  • 1 BA,
  • Sleeps 5
6 night min stay
(3)
$225 - $282
per night
4 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night min stay
(3)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night min stay
(8)
$1,200 - $1,850
per week
7 night min stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
7 night min stay
(6)
  • 4 BR,
  • 3 BA,
  • Sleeps 9
4 - 7 night min stay
(5)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
3 - 14 night min stay
(6)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 7 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(5)
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Recent Gloucester and Annisquam Reviews

Nice, cozy, clean home near the beach

4 of 5
Lovely, clean and near Good Harbor Beach, which was beautiful and such fun for our dog to run around on with all the other dogs. Everything was as expected. Near the village, grocery store and train station to Boston. Highly recommended for anyone looking for a simple and clean place to land while staying in Gloucester.
  • Submitted: Apr 13, 2015
  • Stayed: Mar 2015

Greats family memories

5 of 5
We rented the house from Richard for the past 3 summers. We feel like at home in this beautiful house! Our 2 littles princesses and us love everything about this place: the veranda to drink our morning coffee , the big gallery where the kids can run and play domino's outside with their grand father and father, the confortable living room in the evening, the big table to have wonderful diners (seafoods naturally!) and the little alcove beetween two of the three bedrooms upstairs. All of this made our 3 stays at this place one of our best summer vacations memories. The cleanliness of the house is perfect. The fact that it's so close to the beach was the main reason why we choose this house. And we were very satisfied of our choice: my husband took us by car to the beach drop zone, return to the house and came back by foot. Wondeful! And the GoodHarbor Beach is such a beatiful place. Richard is a very nice guy: it's always a pleasure to talk with him each year. If you want to go to Gloucester, you have to reserve this house!
  • Submitted: Mar 7, 2015
  • Stayed: Aug 2014

AMAZING HOUSE / AMAZING VIEW / AMAZING OWNER

5 of 5
I booked a long weekend at this house to “try it out” for an extended summer stay. So often places look incredible online only to be disappointing when seen in-person. This home was so much more than I ever imagined. But before I share more about the home, I have to say what made this weekend get-away even more special was the owner. Kathy was extremely caring, responsive and a delight to interact with. From the first email, she made us feel like her personal guests versus renters. And we continued to share our vacation experiences with her during our stay. It was a lot of fun. As for the property, I was blown away. I’m a complete neat freak and the property was in perfect order. We immediately felt at home and of course were thrilled with the panoramic views of the harbor and working waterfront. These are not “peek-a-boo” views from a window or two. These views can be easily enjoyed from the kitchen, family room, porch / deck and HUGE master bedroom. I especially LOVED sitting up in bed and watching the sunrise over the harbor. From the minute we walked in, we felt at home. It is a VERY spacious home but at the same time is extremely cozy. It is NOT a rental home with rental-type furnishings. We were there during one of the many blizzards of 2015, so we made full use of the woodstove (that Kathy had already stacked for a fire when we arrived). We also enjoyed playing the grand piano in the formal living room. As for location, it is within easy walking distance to downtown, the waterfront, etc. I could go on and on (even more), but this long weekend was AMAZING!! We have already booked 2 more weeks in July. I honestly cannot imagine how anyone could ever be disappointed staying here and enjoying interacting with Kathy.
  • Submitted: Feb 23, 2015
  • Stayed: Feb 2015