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Our top choices for Bailey Island vacation homes

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
9.8 out of 10, Exceptional, (10 reviews)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is AED 1,309
AED 2,364 total
includes taxes & fees
24 May - 25 May
Orchid Harbor, Bailey Island 3BR

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 AED 386
AED 776 total
includes taxes & fees
7 May - 8 May
2 bedroom w/ expansive water views

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 AED 463
AED 892 total
includes taxes & fees
18 May - 19 May
Mid Coast Getaway w/ water views

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 AED 675
AED 1,198 total
includes taxes & fees
18 May - 19 May
Fantastic Waterfront Views

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 AED 694
AED 1,249 total
includes taxes & fees
8 May - 9 May
Camp Forever cottage

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 AED 752
AED 923 total
includes taxes & fees
12 May - 13 May
Captain's House 2BR Guest Suite. Discover the authenticity & best value in Bath!

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
South Portland Beach area rental

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
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 AED 1,194
AED 1,998 total
includes taxes & fees
6 May - 7 May
Modern Getaway by the Sea

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 AED 378
AED 1,381 total
includes taxes & fees
13 May - 14 May
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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 AED 1,084
AED 1,754 total
includes taxes & fees
8 May - 9 May
Centerview cottage

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is AED 1,397
AED 2,464 total
includes taxes & fees
27 May - 28 May
Mere Point Sunrise Views at Eastern Shore!

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 AED 826
AED 1,457 total
includes taxes & fees
27 May - 28 May
Full sized home

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 694
AED 1,331 total
includes taxes & fees
12 May - 13 May
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

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, (40 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is AED 992
AED 1,718 total
includes taxes & fees
7 May - 8 May
Modern & Sunny House Steps from the Promenade. Private Parking!

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
The price is AED 869
AED 2,873 total
includes taxes & fees
19 May - 20 May
Charming Historic home steps away from downtown

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 AED 1,139
AED 2,150 total
includes taxes & fees
12 May - 13 May
The Globe House on Munjoy Hill - Walk to Breweries

Fort Popham Ocean Estate

Fort Popham Ocean Estate
Phippsburg
10.0 out of 10, Exceptional, (2 reviews)
"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 AED 794
AED 2,571 total
includes taxes & fees
6 May - 7 May
Fort Popham Ocean Estate

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 AED 808
AED 2,606 total
includes taxes & fees
18 May - 19 May
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

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 AED 1,561
AED 2,366 total
includes taxes & fees
10 May - 11 May
Award Winning Luxury Carriage House a short stroll from town!
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

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