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

Our top choices for Bailey Island vacation 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 ￥36,047
￥63,914 total
includes taxes & fees
Sep 22 - Sep 23
Full sized home
TV

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 ￥25,167
￥45,339 total
includes taxes & fees
Sep 14 - Sep 15
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 ￥33,556
￥58,696 total
includes taxes & fees
Sep 7 - Sep 8
Camp Forever cottage
TV

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 ￥26,006
￥46,253 total
includes taxes & fees
Sep 7 - Sep 8
2 bedroom w/ expansive water views
TV, fireplace, books

5. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
The price is ￥10,574
￥44,531 total
includes taxes & fees
Sep 23 - Sep 24
1 Mi to Maine Street! MCM-Style Home in Brunswick
TV, offices

6. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
Fully Updated Airy Historic Home in South Freeport
Property grounds

7. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is ￥35,246
￥60,202 total
includes taxes & fees
Sep 3 - Sep 4
Captains Watch: A Coastal Escape
Property grounds

8. 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 ￥47,138
￥73,326 total
includes taxes & fees
Sep 7 - Sep 8
Centerview cottage
Property grounds

9. 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 ￥95,874
￥301,839 total
includes taxes & fees
Sep 9 - Sep 10
Classic New England Waterfront House Big Lawn Beautiful Sunrise
3 bedrooms, WiFi, bed sheets

10. 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 ￥43,623
￥68,833 total
includes taxes & fees
Sep 9 - Sep 10
Fantastic Waterfront Views
Property grounds

11. 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 ￥15,819
￥25,951 total
includes taxes & fees
Sep 3 - Sep 4
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Outdoor dining

12. 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 ￥16,698
￥26,910 total
includes taxes & fees
Sep 7 - Sep 8
Guest room + bath in Bath!. Authenticity. Value. Large yard. Walk to everything.
Coffee/tea maker, fridge, microwave, dishwasher

13. Quiet Spot in Lovely Freeport Neighborhood

Quiet Spot in Lovely Freeport Neighborhood
Freeport
The price is ￥27,242
￥70,830 total
includes taxes & fees
Sep 14 - Sep 15
Quiet Spot in Lovely Freeport Neighborhood
Coffee/tea maker, fridge, microwave, oven

14. 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 ￥34,312
￥108,463 total
includes taxes & fees
Sep 7 - Sep 8
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Smart TV

15. Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (7 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Coffee/tea maker, fridge, microwave, oven

16. 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 price is ￥119,843
￥377,255 total
includes taxes & fees
Sep 21 - Sep 22
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Interior

17. 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 ￥14,837
￥58,082 total
includes taxes & fees
Sep 3 - Sep 4
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior

18. 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 ￥40,053
￥119,796 total
includes taxes & fees
Sep 14 - Sep 15
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Interior

19. 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 ￥54,648
￥97,884 total
includes taxes & fees
Sep 6 - Sep 7
Lush Coastal Downtown Home - Beaches & Shopping
Desk, iron/ironing board, WiFi (free), bed sheets

20. 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 ￥34,086
￥63,786 total
includes taxes & fees
Sep 29 - Sep 30
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
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

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent
"Nice and clean hotel with friendly staff. We went the last week of August and didn’t have a problem finding street parking at all. Valet is $40 if you don’t want to bother with looking for parking."
Duy 2-night trip
Posted 1 hour ago
Cambria Hotel Portland Downtown-Old Port

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
281
Accommodation
612 Vacation Homes
Lowest Price
￥25,951
Highest Price
￥377,255