Holiday Homes in Bailey Island

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Bailey Island holiday homes

Living area

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is €184
includes taxes & fees
2 Feb - 3 Feb
Escape to Positive Outlook
3 bedrooms, WiFi

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is €216
includes taxes & fees
2 Feb - 3 Feb
Fantastic Waterfront Views
Interior

Entire ideally located home in Cape Elizabeth’s coveted seaside community

Entire ideally located home in Cape Elizabeth’s coveted seaside community
Cape Elizabeth
10.0 out of 10, Exceptional, (4 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
Entire ideally located home in Cape Elizabeth’s coveted seaside community
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, (1 review)
"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 €367
includes taxes & fees
2 Feb - 3 Feb
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Smart TV

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
Beautiful 3BR Home with Office in Town of Brunswick with King beds
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, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is €281
includes taxes & fees
2 Feb - 3 Feb
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is €290
includes taxes & fees
2 Feb - 3 Feb
Full sized home
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is €322
includes taxes & fees
5 Feb - 6 Feb
Modern Getaway by the Sea
Interior

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
9.0 out of 10, Wonderful, (25 reviews)
"Great host communication, arrival and access were easy, house was very clean and comfortable. Will definitely stay again and recommend to fellow Bowdoin families. House is in a great family neighborhood- enjoyed seeing how creative neighbors were with Halloween- would be a great place for kids! Close to town, Bowdoin and so much midcoast has to offer and explore! Thank you!"
United States
Alison O.
The price is €325
includes taxes & fees
2 Feb - 3 Feb
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Property grounds

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
Modern Cottage with Peeks of Ocean Views
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is €474
includes taxes & fees
1 Mar - 2 Mar
Willard Square Family Home
Exterior

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
8.8 out of 10, Excellent, (3 reviews)
"Great location"
United States
Mark J.
The 87th Townhome - Local Landmark
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, (58 reviews)
"Wasn’t clean. Ran out of TP. Requested more but didn’t get any. So had to buy some. Need curtains on the windows. Would be nice to have something to put the luggage on in the rooms so not having to get things off the floor. With one bathroom it would be nice to have more mirrors to use when getting ready. "
United States
Anonymous traveller
The price is €256
includes taxes & fees
4 Mar - 5 Mar
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
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, (8 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
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 €201
includes taxes & fees
2 Feb - 3 Feb
Charming 1-bedroom ADU in wonderful Portland neighborhood
Exterior

Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
The price is €640
includes taxes & fees
2 Feb - 3 Feb
Charming Historic home steps away from downtown
TV, offices

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
Windham
The price is €590
includes taxes & fees
2 Feb - 3 Feb
Modern Lakeview Escape | 3BR/2BA
Property grounds

Maine Oceanfront Retreat

Maine Oceanfront Retreat
Brunswick
10.0 out of 10, Exceptional, (1 review)
"Gorgeous views house is extremely well equipped "
United States
Cary C.
The price is €919
includes taxes & fees
2 Feb - 3 Feb
Maine Oceanfront Retreat
Property grounds

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Georgetown
The price is €266
includes taxes & fees
5 Feb - 6 Feb
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Exterior detail

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (66 reviews)
"Perfect for our girls trip! Right outside portland with gorgeous views; Meghan was so very accommodating as well!"
United States
Allysa Z.
The price is €886
includes taxes & fees
2 Feb - 3 Feb
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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

LivAway Suites Portland-Scarborough

LivAway Suites Portland-Scarborough

10/10 Excellent
"Great spot felt like a home away from home. Nice new and very clean."
Ahmed 2-night trip
Posted 4 days ago
LivAway Suites Portland-Scarborough

Find out more about Bailey Island

Bailey Island Holiday Homes information

Number of reviews
280
Accommodation
509 Holiday Homes
Lowest Price
€201
Highest Price
€919