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Bailey Island Long Term Vacation Rentals(13)

13 Results
$400 - $1,000
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(18)
$200 - $310
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night minimum stay
(11)
$2,200
per week
7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(12)
$2,000
per week
4 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 31 night minimum stay
(5)
$90 - $110
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 - 7 night minimum stay
1 Review
$1,500 - $2,000
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(6)
$132 - $200
per night
3 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(7)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(3)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 15
7 night minimum stay
$100
per night
6 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
2 Reviews
$975
per week
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
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Recent Bailey Island Reviews

A New England Classic Updated!

5 of 5
This is a new house with state of the art geothermal heating and solar panels on the roof. Granola sounding as that might be though this is an exquisite home in the classic New England style set on Casco Bay. The windows in each room are unadorned and fill the house with light and offer clear - and magnificent views - of the water and the lobster boaters at work. It is fully - and nicely - equipped though minus one blue goblet which is the result of a bit of careless clean-up on our part ! There is lots to do in the area - or nothing to do but sit and relax either inside or on one of the red chairs set at the edge of the beach.. These are wonderful alternatives. We give Friendly Cottage and its owners an A plus. Our only complaint? More pillows please..
  • Submitted: Oct 30, 2014
  • Stayed: Oct 2014

Rustic charm on Baily Island

5 of 5
My boyfriend and I stayed at windward ho for our anniversary in September, and it couldn't have been more perfect. The location is ideal with a view of the water. There is also beach access a short walk away. The cottage is well equipped with wifi, plenty of outlets, and everything you need in the kitchen. Although, it has plenty of modern amenities it also still has a rustic charm that is just want I wanted on a trip to Maine. Joan was very helpful and nice. I definitely would love to come back for a longer stay next year!
  • Submitted: Sep 30, 2014
  • Stayed: Sep 2014

Better Late than Never

4 of 5
We stayed for a week in your beautiful "cottage". Everything was perfect, especially having Lexi grazing in the yard next to us. The view from the deck was just wonderful while enjoying our coffee in the morning, glass of wine in the evening. My friend and I have both been to Bailey Island and thus the reason for coming back. Our memories of being there in the past with loved ones will live on forever . We love the Giant Stairs and being near Brunswick, and also the few restaurants on the island. We would definitely recommend the cottage and of course the location.
  • Submitted: Sep 29, 2014
  • Stayed: Jul 2014