Bailey Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Bailey Island vacation homes

The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (11 reviews)
"Very comfortable, clean, with a spacious bathroom and within walking distance of downtown Freeport and Bow Street Market"
United States
Deanna S.
The price is CA $92
CA $197 total
includes taxes & fees
Feb 17 - Feb 18
The Outlet Studio, Rustic Comfort w Fireplace

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 CA $143
CA $293 total
includes taxes & fees
Feb 24 - Feb 25
Escape to Positive Outlook

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 CA $245
CA $464 total
includes taxes & fees
Feb 18 - Feb 19
Full sized home

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 CA $272
CA $528 total
includes taxes & fees
Feb 21 - Feb 22
Modern Getaway by the Sea

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 CA $255
CA $504 total
includes taxes & fees
Feb 22 - Feb 23
Modern & Sunny House Steps from the Promenade. Private Parking!

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 CA $179
CA $377 total
includes taxes & fees
Mar 17 - Mar 18
Fantastic Waterfront Views

1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Good communication with host. Beautifully decorated. Well appointed kitchen and bath. Great wooded views. Quiet but close to restaurants and shopping."
United States
Lecia M.
The price is CA $90
CA $316 total
includes taxes & fees
Feb 24 - Feb 25
1 Mi to Maine Street! MCM-Style Home in Brunswick

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)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is CA $192
CA $416 total
includes taxes & fees
Feb 18 - Feb 19
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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 CA $211
CA $602 total
includes taxes & fees
Feb 16 - Feb 17
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Charming Historic home steps away from downtown

Charming Historic home steps away from downtown
Bath
The price is CA $290
CA $1,040 total
includes taxes & fees
Feb 17 - Feb 18
Charming Historic home steps away from downtown

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is CA $238
CA $381 total
includes taxes & fees
Feb 18 - Feb 19
Charming 1-bedroom ADU in wonderful Portland neighborhood

Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
The price is CA $193
CA $902 total
includes taxes & fees
Feb 16 - Feb 17
Windham Lakefront: Fire Pit and Modern Comforts

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

Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi
Georgetown
The price is CA $221
CA $453 total
includes taxes & fees
Feb 17 - Feb 18
Spruce Studio: Near Beach+FirePit+Pond+Heat/AC+Fast WiFi

Generous Living in a Warm, Welcoming Home

Generous Living in a Warm, Welcoming Home
Topsham
The price is CA $201
CA $672 total
includes taxes & fees
Mar 17 - Mar 18
Generous Living in a Warm, Welcoming Home

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, (67 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 CA $949
CA $1,437 total
includes taxes & fees
Feb 24 - Feb 25
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

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.
The price is CA $388
CA $606 total
includes taxes & fees
Feb 22 - Feb 23
Modern Cottage with Peeks of Ocean Views

Huge Historic Downtown Townhome

Huge Historic Downtown Townhome
West End
9.8 out of 10, Exceptional, (8 reviews)
"The house is so charming and in an excellent location! It is walking distance to many options, on a quiet, beautiful street with comfortable beds and a well appointed kitchen. Easy booking and communication throughout! "
United States
Siobhain C.
The price is CA $279
CA $676 total
includes taxes & fees
Mar 11 - Mar 12
Huge Historic Downtown Townhome

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 CA $347
CA $747 total
includes taxes & fees
Feb 17 - Feb 18
Willard Square Family Home

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 CA $579
CA $889 total
includes taxes & fees
Feb 15 - Feb 16
Award Winning Luxury Carriage House a short stroll from town!

Fort Popham Ocean Estate

Fort Popham Ocean Estate
Phippsburg
The price is CA $275
CA $937 total
includes taxes & fees
Feb 15 - Feb 16
Fort Popham Ocean Estate
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Bailey Island Hotel Reviews

Find out more about Bailey Island

Bailey Island Vacation Homes information

Number of reviews
267
Accommodation
509 Vacation Homes
Lowest Price
CA $197
Highest Price
CA $1,437

Explore a world of travel with Expedia