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Bailey Island Cottage Rentals(31)

31 Results
$2,300 - $2,600
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(23)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night min stay
(11)
$2,200
per week
7 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
(8)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
7 night min stay
(4)
$110 - $196
per night
3 - 7 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(7)
$1,500 - $2,000
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 7
7 night min stay
(6)
$90 - $110
per night
3 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 7 night min stay
1 Review
$2,000
per week
4 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 31 night min stay
(5)
  • 2 BR,
  • 1 BA,
  • Sleeps 3
3 - 7 night min stay
(3)
$700
per week
7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night min stay
1 Review
$1,080 - $1,295
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night min stay
(3)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
(3)
$190
per night
3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 night min stay
(8)
$100
per night
6 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 4
6 night min stay
2 Reviews
$1,400 - $2,800
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night min stay
1 Review
$975
per week
7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
7 night min stay
$200 - $243
per night
4 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
$136 - $164
per night
4 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 7 night min stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 7
4 - 7 night min stay
$236 - $264
per night
4 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night min stay
$271 - $300
per night
4 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night min stay
2 Reviews
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Recent Bailey Island Reviews

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

A quintessential Maine cottage

5 of 5
We have been staying at the Washburn Cottage for many years now. We look forward to our stay all year long, as it is the highlight of every summer for our family. Some of the best parts of our stay have been sunsets seen from the back porch, the access to the shoreline where we can walk along the water, the rustic, cottage feel of the Washburn and the central location to everything the island has to offer. We really enjoy visiting the restaurants in the immediate area, such as The Cribstone restaurant, BIGS and the Saltwater Cafe, along with many other restaurants in the surrounding Harpswell area. We have found many hiking and walking trails in the area, one of our favorites being Mitchell Field on Harpswell. But most of all, we just love being able to sit on the back porch at the cottage and relax without feeling like we have to go anywhere. In conclusion, we absolutely LOVE the Washburn Cottage and look forward to returning for many summers to come.
  • Submitted: Sep 1, 2014
  • Stayed: Aug 2014