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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Bailey Island vacation homes

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

1. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is AED 634
AED 1,485 total
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 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 AED 270
AED 618 total
includes taxes & fees
2 Nov - 3 Nov
Mid Coast Getaway w/ water views
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

3. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 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 AED 482
AED 849 total
includes taxes & fees
8 Nov - 9 Nov
2 bedroom w/ expansive water views
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

4. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
The price is AED 566
AED 1,013 total
includes taxes & fees
16 Nov - 17 Nov
Captains Watch: A Coastal Escape
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

5. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (23 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AED 463
AED 902 total
includes taxes & fees
2 Nov - 3 Nov
Fantastic Waterfront Views
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is AED 512
AED 1,350 total
includes taxes & fees
16 Nov - 17 Nov
Mere Point Sunrise Views at Eastern Shore!
A wooden deck with outdoor seating and string lights.

7. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 735
AED 1,277 total
includes taxes & fees
30 Nov - 1 Dec
Full sized home
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

8. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
Fully Updated Airy Historic Home in South Freeport
A lush garden with a hammock, a variety of flowers, and a lake in the background.

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 AED 1,286
AED 5,869 total
includes taxes & fees
30 Nov - 1 Dec
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

10. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AED 520
AED 1,410 total
includes taxes & fees
2 Nov - 3 Nov
Quiet Spot in lovely Freeport neighborhood
A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

11. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is AED 1,212
AED 2,955 total
includes taxes & fees
2 Nov - 3 Nov
Casco Bay Oceanfront Retreat by Everrow
A treehouse with a wooden staircase and a small building with a colorful mural.

12. Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,

Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
Bath
8.0 out of 10, Very good, (31 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 AED 444
AED 628 total
includes taxes & fees
2 Nov - 3 Nov
Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

13. 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 AED 624
AED 1,493 total
includes taxes & fees
2 Nov - 3 Nov
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
A wooden staircase with a wooden railing, surrounded by green foliage.

14. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AED 454
AED 639 total
includes taxes & fees
2 Nov - 3 Nov
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
A bedroom with a bed, a window with a view, a chair, and a lamp.

15. 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 AED 2,149
AED 7,607 total
includes taxes & fees
2 Nov - 3 Nov
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

16. 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, (5 reviews)
"Great location and super clean house"
United States
Gary R.
The price is AED 900
AED 2,586 total
includes taxes & fees
8 Nov - 9 Nov
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

17. Newly Renovated Luxury House with Game Room

Newly Renovated Luxury House with Game Room
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is AED 1,069
AED 2,786 total
includes taxes & fees
2 Nov - 3 Nov
Newly Renovated Luxury House with Game Room
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

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

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AED 370
AED 1,300 total
includes taxes & fees
2 Nov - 3 Nov
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A building named Willard Square with a storefront and a red vehicle parked outside.

19. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AED 1,315
AED 2,360 total
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

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 AED 774
AED 1,396 total
includes taxes & fees
2 Nov - 3 Nov
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"The staff were friendly. We had a hard time checking in but it was fine. On our second night a staff came to our door knocking. He said we never checked in. We have been there a full day and night. But all and all it was ok."
Christina 2-night trip
Posted 11 hours ago
Inn at St John Portland In-Town