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Gloucester and Annisquam House Rentals(80)

80 Results
  • 6 BR,
  • 2 BA,
  • Sleeps 13
2 night minimum stay
(17)
$300
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(42)
  • 5 BR,
  • 2 BA,
  • Sleeps 12
2 - 7 night minimum stay
(4)
  • 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
  • 7 BR,
  • 3 BA,
  • Sleeps 16
4 - 7 night minimum stay
(22)
  • 5 BR,
  • 3 BA,
  • Sleeps 11
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
(5)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(3)
$50 - $250
per night
2 - 180 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 180 night minimum stay
(6)
$2,095 - $2,195
per week
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
7 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(5)
$429 - $450
per night
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 13
2 - 7 night minimum stay
(9)
$1,600 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(21)
$125 - $171
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
2 - 7 night minimum stay
(6)
$2,450 - $3,250
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 11
7 night minimum stay
(9)
$500 - $550
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night minimum stay
2 Reviews
$110 - $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
1 Review
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
$200 - $250
per night
3 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 4 night minimum stay
$357 - $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,
  • Sleeps 5
6 night minimum stay
2 Reviews
$321 - $650
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(6)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night minimum stay
(8)
$1,200 - $1,850
per week
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(6)
  • 4 BR,
  • 3 BA,
  • Sleeps 9
4 - 7 night minimum stay
(5)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
3 - 31 night minimum stay
(6)
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Recent Gloucester and Annisquam Reviews

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

Lovely home and wonderful owners

5 of 5
My family and I rented this wonderful renovated historical home for 5 weeks during the summer of 2014. It was perfectly appointed, and the owners were exceptionally warm and accomodating. My young children loved watching the tide come in and out of the tidal inlet, and we had the daily company of a beautiful blue heron that was fishing at low tide. We enjoyed the short walk to plum cove beach and also to Annisquam Village. The home was spotless and was decorated so nicely. The view was incredible. We could not have asked for a better experience.
  • Submitted: Jan 22, 2015
  • Stayed: Jul 2014

Best of Both Worlds!

5 of 5
Perfect secluded location for enjoying the ocean views and breezes without the constant noise and traffic that go along with some beachfront locations. Perfect deck and common areas for entertaining. Highly recommend!
  • Submitted: Jan 20, 2015
  • Stayed: Jul 2014