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

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 ￥27,192
￥66,930 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥14,824
￥32,028 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥19,766
￥38,098 total
includes taxes & fees
Nov 1 - Nov 2
2 bedroom w/ expansive water views
A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

4. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is ￥13,218
￥51,927 total
includes taxes & fees
Oct 28 - Oct 29
Quiet Spot in lovely Freeport neighborhood
A covered porch with a view of a lake and trees.

5. 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 ￥22,866
￥61,917 total
includes taxes & fees
Nov 17 - Nov 18
Mere Point Sunrise Views at Eastern Shore!
A wooden deck with outdoor seating and string lights.

6. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (79 reviews)
"Wonderful stay!"
United States
Erika T.
The price is ￥31,766
￥57,880 total
includes taxes & fees
Nov 9 - Nov 10
Full sized home
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

7. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
10.0 out of 10, Exceptional, (1 review)
"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 ￥25,884
￥29,304 total
includes taxes & fees
Nov 1 - Nov 2
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.

8. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (22 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ￥24,707
￥28,469 total
includes taxes & fees
Nov 1 - Nov 2
Fantastic Waterfront Views
A lakeside property with a deck, picnic table, and barbecue grill.

9. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"We had a really nice day in communication and check-in were very easy. Overall, it was a lovely day and we would definitely consider returning."
United States
Len B.
The price is ￥32,943
￥56,939 total
includes taxes & fees
Nov 1 - Nov 2
Camp Forever cottage
A lush garden with a hammock, a variety of flowers, and a lake in the background.

10. 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 ￥54,905
￥263,664 total
includes taxes & fees
Nov 23 - Nov 24
Classic New England Waterfront House Big Lawn Beautiful Sunrise
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 ￥58,137
￥141,133 total
includes taxes & fees
Oct 28 - Oct 29
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 ￥17,507
￥27,802 total
includes taxes & fees
Oct 30 - Oct 31
Guest Room + Bath + Private Emtrance. Walk to everything, Large yard,
A wooden staircase with a wooden railing, surrounded by green foliage.

13. 1BR Apt. Authenticity. Value. Walk to everything, Large yard.

1BR Apt. Authenticity. Value. Walk to everything, Large yard.
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is ￥19,373
￥29,667 total
includes taxes & fees
Oct 30 - Oct 31
1BR Apt. Authenticity. Value. 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.

14. 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 ￥26,668
￥66,515 total
includes taxes & fees
Nov 1 - Nov 2
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

15. 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 ￥38,433
￥116,272 total
includes taxes & fees
Nov 9 - Nov 10
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

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 ￥91,769
￥358,392 total
includes taxes & fees
Oct 28 - Oct 29
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

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, (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 ￥55,421
￥137,658 total
includes taxes & fees
Nov 1 - Nov 2
Luxe 5 Bed/ 3 Bath with Game Room & AC
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
8.4 out of 10, Very good, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is ￥15,121
￥57,178 total
includes taxes & fees
Oct 29 - Oct 30
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

19. 2BR Apt. Authenticity. Value. Walk to everything, Large yard, Treehouse. 0 fees.

2BR Apt. Authenticity. Value. Walk to everything, Large yard, Treehouse. 0 fees.
Bath
8.8 out of 10, Excellent, (29 reviews)
"Nice place for the money spent"
United States
Kevin P.
The price is ￥32,472
￥40,011 total
includes taxes & fees
Oct 30 - Oct 31
2BR Apt. Authenticity. Value. Walk to everything, Large yard, Treehouse. 0 fees.
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 ￥33,037
￥62,016 total
includes taxes & fees
Nov 1 - Nov 2
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

Clarion Pointe South Portland

Clarion Pointe South Portland

8/10 Good
"Decent hotel, great price too. Pool was awesome."
Hannah 1-night trip
Posted less than an hour ago
Clarion Pointe South Portland

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
344
Accommodation
613 Vacation Homes
Lowest Price
￥27,802
Highest Price
￥358,392