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Check prices for these dates

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

Our top choices for Bailey Island vacation 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 ￥13,404
￥30,057 total
includes taxes & fees
Apr 30 - May 1
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 ￥30,159
￥53,745 total
includes taxes & fees
Apr 30 - May 1
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 ￥25,107
￥45,218 total
includes taxes & fees
May 4 - May 5
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 ￥20,086
￥37,325 total
includes taxes & fees
May 3 - May 4
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 ￥47,026
￥75,411 total
includes taxes & fees
May 3 - May 4
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 ￥32,648
￥40,108 total
includes taxes & fees
May 11 - May 12
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 ￥14,763
￥57,098 total
includes taxes & fees
May 1 - May 2
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Beach

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
The price is ￥19,646
￥43,155 total
includes taxes & fees
Apr 30 - May 1
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 ￥51,808
￥85,330 total
includes taxes & fees
May 1 - May 2
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 ￥27,897
￥44,656 total
includes taxes & fees
May 13 - May 14
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.
The price is ￥55,794
￥123,973 total
includes taxes & fees
Apr 30 - May 1
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 ￥34,831
￥121,280 total
includes taxes & fees
May 12 - May 13
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 ￥35,903
￥63,311 total
includes taxes & fees
May 27 - May 28
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 ￥35,070
￥113,116 total
includes taxes & fees
May 18 - May 19
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 ￥43,041
￥75,063 total
includes taxes & fees
May 14 - May 15
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 ￥34,467
￥63,573 total
includes taxes & fees
May 27 - May 28
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 ￥67,749
￥102,690 total
includes taxes & fees
May 3 - May 4
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 price is ￥49,467
￥93,401 total
includes taxes & fees
May 12 - May 13
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 ￥34,489
￥110,992 total
includes taxes & fees
May 5 - May 6
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.
The price is ￥54,429
￥114,464 total
includes taxes & fees
Apr 30 - May 1
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Centrally located. Room very clean, if a bit tight. Friendly staff, we genuinely felt welcome. "
Kimberly 2-night trip
Posted 7 hours ago
Portland Regency Hotel & Spa

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
457
Accommodation
546 Vacation Homes
Lowest Price
￥30,057
Highest Price
￥123,973