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Portland and Casco Bay Area Long Term Cottage Rentals(68)

68 Results
$1,150
per week
3 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night min stay
(11)
$168 - $190
per night
4 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
4 - 7 night min stay
(6)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
2 Reviews
$467 - $2,000
per week
7 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 30 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 3 night min stay
(11)
$2,500 - $3,000
per week
7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
(3)
$400 - $416
per night
3 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night min stay
(4)
$2,200
per week
7 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
2 Reviews
$105 - $145
per night
2 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night min stay
(15)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
(6)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
(5)
$155
per night
5 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
5 night min stay
(13)
$1,400
per week
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night min stay
1 Review
$55 - $300
per night
1 - 90 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
1 - 90 night min stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(11)
$2,800 - $3,200
per week
7 night min stay
  • 6 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
2 Reviews
$110 - $196
per night
3 - 7 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(7)
$142 - $230
per night
5 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
5 - 7 night min stay
2 Reviews
$225
per night
3 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
3 night min stay
(4)
$1,500 - $2,000
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 7
7 night min stay
(6)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
(3)
  • 3 BR,
  • 1 BA,
  • Sleeps 7
2 - 7 night min stay
(4)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
5 - 7 night min stay
(14)
  • 3 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night min stay
(4)
$90 - $110
per night
3 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 7 night min stay
1 Review
  • 4 BR,
  • 1 BA,
  • Sleeps 10
7 night min stay
$165 - $214
per night
3 - 7 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night min stay
(3)
$2,000
per week
4 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 31 night min stay
(5)
 

Recent Portland and Casco Bay Area Reviews

Quaint and Cozy, lots of character!

4 of 5
We stayed with our 2,3 yr old sons. The location is great. I was so pleased to see it nestled among other well maintained and beautiful homes. This has obviously been a loved and cared for family cottage for many generations. It is very basic, but not overly rustic and had lots of nice touches to make our stay pleasant. We live in a two story home, but my kids did find the stairs a challenge so it may be better suited to a slightly older kids who won't peg your heart rate every time they go near the steps! But hey, your vacation. Choose your own adventure. Over all for price, location and great owners who responded quickly to any question we had, this is a great find on HomeAway. Thank You!
  • Submitted: Mar 18, 2015
  • Stayed: Jun 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