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Gloucester and Annisquam House Rentals(84)

84 Results
  • 6 BR,
  • 2 BA,
  • Sleeps 13
2 night minimum stay
(17)
  • 5 BR,
  • 2 BA,
  • Sleeps 12
2 - 7 night minimum stay
(4)
$300
per night
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(41)
  • 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)
  • 7 BR,
  • 3 BA,
  • Sleeps 16
4 - 7 night minimum stay
(22)
  • 6 BR,
  • 3 BA,
  • Sleeps 15
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 11
7 night minimum stay
$350 - $2,100
per week
7 - 30 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
7 - 30 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)
$425 - $450
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(3)
$50 - $185
per night
1 - 31 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
1 - 31 night minimum stay
(6)
$429 - $450
per night
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 13
2 - 7 night minimum stay
(9)
$1,575 - $2,100
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(21)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night minimum stay
2 Reviews
$125
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)
$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
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
$2,095 - $2,350
per week
7 night minimum stay
  • 4 BR,
  • 1 BA,
  • Sleeps 7
7 night minimum stay
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
$321 - $650
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(6)
$357 - $385
per night
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
7 - 31 night minimum stay
(6)
$1,200 - $1,850
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 6
7 night minimum stay
(5)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 30 night minimum stay
(8)
$220 - $275
per night
3 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 4 night minimum stay
$2,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(5)
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Recent Gloucester and Annisquam Reviews

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

Amazing Vacation Spot!

5 of 5
We have rented this incredible house for the second year in a row and have never regretted our decision. Amazing property, spacious, located on the shore of a beautiful pond, short drive from Boston and walking distance away from a convenience store - this house is perfect for a short weekend getaway or and extended vacation stay! It has everything that is advertised and much more. The owners and management are very helpful, responsive and a pleasure to work with overall. Everyone who stayed with us at this house can't wait to book it for next year! If you are looking for a perfect getaway look no further!
  • Submitted: Jan 9, 2015
  • Stayed: Dec 2014

Wonderful Place to stay

5 of 5
We love Lisa's Lookout!! We've been staying there for about 2 1/2 years now. We stay a few times a year!!! Lisa's Lookout is simply amazing!! Comfortable beds, everything you need is right there. Since staying there we REFUSE to stay any place else. You will not be disappointed. Lisa and Capt Kevin are 2 of the most wonderful people that we have ever had a chance to meet!!!
  • Submitted: Dec 25, 2014
  • Stayed: Aug 2014