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

Holiday Homes in Bailey Island

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Bailey Island holiday homes

A wooden deck with outdoor seating and string lights.

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (69 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is €318
includes taxes & fees
5 Oct - 6 Oct
Full sized home
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, (10 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 €184
includes taxes & fees
28 Sept - 29 Sept
Mid Coast Getaway w/ water views
A lakeside property with a deck, picnic table, and barbecue grill.

3. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is €323
includes taxes & fees
3 Oct - 4 Oct
Camp Forever cottage
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.

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 €226
includes taxes & fees
29 Sept - 30 Sept
2 bedroom w/ expansive water views
A treehouse with a wooden staircase and a small building with a colorful mural.

5. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (30 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 €159
includes taxes & fees
26 Sept - 27 Sept
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A spacious living room with large windows, a sofa, a chair, and a small table.

6. 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.
1 Mi to Maine Street! MCM-Style Home in Brunswick
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

7. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €185
includes taxes & fees
28 Sept - 29 Sept
Fantastic Waterfront Views
A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

8. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €339
includes taxes & fees
25 Sept - 26 Sept
Quiet Spot in lovely Freeport neighborhood
A wooden deck with a view of a lake, surrounded by trees and shrubs.

9. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is €415
includes taxes & fees
27 Sept - 28 Sept
Centerview cottage
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

10. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is €192
includes taxes & fees
28 Sept - 29 Sept
Captains Watch: A Coastal Escape
A wooden staircase with a wooden railing, surrounded by green foliage.

11. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is €164
includes taxes & fees
25 Sept - 26 Sept
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A covered porch with a view of a lake and trees.

12. 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 €377
includes taxes & fees
14 Oct - 15 Oct
Mere Point Sunrise Views at Eastern Shore!
A lush garden with a hammock, a variety of flowers, and a lake in the background.

13. 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 €1,578
includes taxes & fees
12 Oct - 13 Oct
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

14. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
Three bedroom in United States of America, Freeport
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.

15. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (27 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is €210
includes taxes & fees
28 Sept - 29 Sept
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
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"
United States
Ashley W.
The price is €650
includes taxes & fees
28 Sept - 29 Sept
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

17. 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 €357
includes taxes & fees
25 Oct - 26 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

18. 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 €2,038
includes taxes & fees
5 Oct - 6 Oct
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

19. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 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 €522
includes taxes & fees
26 Sept - 27 Sept
Lush Coastal Downtown Home - Beaches & Shopping
A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

20. Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
9.0 out of 10, Wonderful, (2 reviews)
"The communication was excellent. The location was excellent."
United States
Holly Y.
The price is €650
includes taxes & fees
6 Oct - 7 Oct
Charming Historic home steps away from downtown
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Hotel was very nice and clean rooms updated and hotel staff friendly and helpful. I recommend if staying in old port area. Valet is $40 a night as parking options are limited downtown but other than that a very nice hotel."
Elizabeth 1-night trip
Posted less than an hour ago
Portland Regency Hotel & Spa

Find out more about Bailey Island

Bailey Island Holiday Homes information

Number of reviews
365
Accommodation
541 Holiday Homes
Lowest Price
€159
Highest Price
€2,038