Holiday Homes in Bailey Island

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 June - 28 June
In three months
24 July - 26 July
In four months
21 Aug - 23 Aug

Our top choices for Bailey Island holiday homes

TV

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (5 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$302
includes taxes & fees
3 May - 4 May
Mid Coast Getaway w/ water views
Terrace/patio

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$471
includes taxes & fees
1 May - 2 May
Camp Forever cottage
3 bedrooms, WiFi

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.8 out of 10, Exceptional, (16 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is AU$410
includes taxes & fees
3 May - 4 May
Fantastic Waterfront Views
TV

2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (3 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 AU$337
includes taxes & fees
3 May - 4 May
2 bedroom w/ expansive water views
Property grounds

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (59 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is AU$652
includes taxes & fees
1 May - 2 May
Centerview cottage
Property grounds

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Bath
8.6 out of 10, Excellent, (10 reviews)
"Clean rooms. Quiet location walkable to much of downtown Bath "
United States
randy k.
The price is AU$349
includes taxes & fees
11 May - 12 May
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!
Interior

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, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is AU$502
includes taxes & fees
1 May - 2 May
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Beach

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
The price is AU$402
includes taxes & fees
3 May - 4 May
South Portland Beach area rental
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is AU$751
includes taxes & fees
1 May - 2 May
Modern Getaway by the Sea
1 bedroom, Internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is AU$388
includes taxes & fees
10 May - 11 May
Charming 1-bedroom ADU in wonderful Portland neighborhood
Smart TV, fireplace, books

Waterfront, Luxury, Spacious home in Freeport!

Waterfront, Luxury, Spacious home in Freeport!
Freeport
10.0 out of 10, Exceptional, (30 reviews)
"Lovely place and beautiful views! "
United Kingdom
Jacque C.
Waterfront, Luxury, Spacious home in Freeport!
Exterior

Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
The price is AU$1,111
includes taxes & fees
11 May - 12 May
Charming Historic home steps away from downtown
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is AU$588
includes taxes & fees
14 May - 15 May
Full sized home
Interior

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, (2 reviews)
"This house was clean and just as described! Close to campus and downtown. Our host was responsive and very helpful!"
United States
Erin B.
The price is AU$986
includes taxes & fees
4 May - 5 May
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Outdoor dining

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (39 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is AU$648
includes taxes & fees
7 May - 8 May
Modern & Sunny House Steps from the Promenade. Private Parking!
Iron/ironing board, free WiFi, bed sheets

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 AU$546
includes taxes & fees
27 May - 28 May
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Fridge, microwave, oven, stovetop

Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (9 reviews)
"An exceptional property and guest. Would love to stay again next time Thank you Jared and Heather!"
United States
Ronald H.
The price is AU$898
includes taxes & fees
1 May - 2 May
Award Winning Luxury Carriage House a short stroll from town!
Outdoor dining

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, (95 reviews)
"Cozy and clean great location "
United States
Michele F.
The Globe House on Munjoy Hill - Walk to Breweries
Interior

Fort Popham Ocean Estate

Fort Popham Ocean Estate
Phippsburg
10.0 out of 10, Exceptional, (1 review)
"We stayed at the Fort Popham Ocean Estate in March 2026. It is a beautiful house equipped with all the comforts of home. It is a charming and cozy place to stay. The location was outstanding. Right on the water and walking distance to beautiful Popham Beach. Two things to note-the location is pretty remote which we knew and really enjoyed. Also, the lower level was significantly colder than the rest of the home which only matters if you are staying during the cold months.Overall we really...
United States
kathy f.
The price is AU$973
includes taxes & fees
4 May - 5 May
Fort Popham Ocean Estate
Interior

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (15 reviews)
"We had a fantastic stay. Alexa was a wonderful host!"
United States
Desmond L.
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
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 Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"Clean, quiet it had breakfast but we had to leave to early."
Joanne 1-night trip
Posted 3 hours ago
Clarion Hotel Portland Airport ME

Find out more about Bailey Island

Bailey Island Holiday Homes information

Number of reviews
457
Accommodation
545 Holiday Homes
Lowest Price
AU$302
Highest Price
AU$1,111