A rocky shoreline with a boat, a house, and a forest in the background.

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Bailey Island holiday homes

Terrace/patio

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is HK$1,764
HK$3,128 total
includes taxes & fees
22 Sept - 23 Sept
Full sized home
Living area

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (8 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is HK$1,235
HK$2,208 total
includes taxes & fees
13 Sept - 14 Sept
Mid Coast Getaway w/ water views
Terrace/patio

3. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,647
HK$2,880 total
includes taxes & fees
6 Sept - 7 Sept
Camp Forever cottage
Living area

4. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is HK$1,276
HK$2,261 total
includes taxes & fees
7 Sept - 8 Sept
2 bedroom w/ expansive water views
Property grounds

5. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is HK$4,704
HK$15,623 total
includes taxes & fees
8 Sept - 9 Sept
Classic New England Waterfront House Big Lawn Beautiful Sunrise
Property grounds

6. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (69 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is HK$2,313
HK$3,598 total
includes taxes & fees
7 Sept - 8 Sept
Centerview cottage
Property grounds

7. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is HK$2,372
HK$3,763 total
includes taxes & fees
26 Sept - 27 Sept
Captains Watch: A Coastal Escape
Room

8. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (18 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is HK$2,882
HK$3,999 total
includes taxes & fees
22 Sept - 23 Sept
Fantastic Waterfront Views
Property grounds

9. Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Bath
8.0 out of 10, Very good, (18 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is HK$776
HK$1,273 total
includes taxes & fees
6 Sept - 7 Sept
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Private kitchen

10. Quiet Spot in Lovely Freeport Neighborhood

Quiet Spot in Lovely Freeport Neighborhood
Freeport
The price is HK$1,333
HK$3,467 total
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in Lovely Freeport Neighborhood
Outdoor dining

11. Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.

Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Bath
8.2 out of 10, Very good, (29 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is HK$819
HK$1,320 total
includes taxes & fees
6 Sept - 7 Sept
Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Private kitchen

12. Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (10 reviews)
"Our whole family was impressed by this house!"
United States
Gary B.
The price is HK$1,684
HK$5,322 total
includes taxes & fees
7 Sept - 8 Sept
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Private kitchen

13. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Interior

14. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (4 reviews)
"Great location and super clean house"
United States
Gary R.
The price is HK$1,960
HK$5,863 total
includes taxes & fees
14 Sept - 15 Sept
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Room

15. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is HK$1,694
HK$3,154 total
includes taxes & fees
29 Sept - 30 Sept
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Interior

16. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is HK$2,980
HK$5,180 total
includes taxes & fees
17 Sept - 18 Sept
Lush Coastal Downtown Home - Beaches & Shopping
Living area

17. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is HK$3,192
HK$7,881 total
includes taxes & fees
8 Sept - 9 Sept
Luxe 5 Bed/ 3 Bath with Game Room & AC
Interior

18. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$963
HK$3,127 total
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior

19. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
8.8 out of 10, Excellent, (28 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
The price is HK$2,156
HK$4,393 total
includes taxes & fees
21 Sept - 22 Sept
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Outdoor dining

20. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is HK$2,509
HK$4,504 total
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bailey Island Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Staff was very friendly and courteous."
Brenda 1-night trip
Posted 2 hours ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
397
Accommodation
612 Vacation Homes
Lowest Price
HK$1,273
Highest Price
HK$15,623

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