Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Cottages
Homes
Apartments
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Condos
Estates
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Bailey Island Vacation Rentals(29)

29 Results
$400 - $900
per night
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(15)
  • 4 BR,
  • 5 BA,
  • Sleeps 12
7 night minimum stay
(8)
$2,300 - $2,600
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(23)
$800 - $1,800
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
1 Review
$543 - $600
per night
2 - 7 night minimum stay
  • 9 BR,
  • 4 BA,
  • Sleeps 24
2 - 7 night minimum stay
(14)
$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)
$214
per night
4 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 11
4 - 7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(11)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 6 night minimum stay
(16)
  • 4 BR,
  • 2 BA,
  • Sleeps 7
(6)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(3)
  • 5 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(7)
$250 - $286
per night
4 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 31 night minimum stay
(5)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
(4)
$1,030
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 3
3 - 7 night minimum stay
(3)
$171 - $229
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 14
3 - 7 night minimum stay
1 Review
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 17
1 Review
10 more choices from the HomeAway Network
$190
per night
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(8)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 Reviews
$100
per night
6 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
6 night minimum stay
2 Reviews
$280
per night
3 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 night minimum stay
(4)
$145 - $174
per night
4 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 2
4 - 7 night minimum stay
1 Review
  • 6 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(3)
$700 - $1,000
per night
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 13
2 - 7 night minimum stay
1 Review
Advertisement
 

Recent Bailey Island Reviews

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

Best birthday ever!

5 of 5
We arrived later in the evening than expected to a couple of lobsters waiting to be cooked! Which we did and thoroughly enjoyed! The Johnson homestead is great, it was fully equipped as described and the views from the front yard at sunset were beautiful. Sunrises from the deck chairs in the backyard with coffee in hand were one of my favorite parts. One morning we even got to go pull lobster pots with Dave on his lobster boat, an amazing treat, I highly recommend. The beds were comfy, I slept better than I had in awhile, awaking to Myron and Myrna the seagulls in residence singing and chirping. Great Places to eat nearby are Giant Stairs and Morses. We loved the sunset sail on a charter out of cooks. We stayed busy but relaxed, we whale watched out of Boothbay Harbor, we shopped in Freeport and walked down to lands end while enjoying an ice cream cone, a wonderful and perfect birthday vacation! Bailey island is a gem!! Thank you Dave!!!
  • Submitted: Aug 28, 2014
  • Stayed: Aug 2014