Search Vacation Homes in Bailey Island

  • 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

Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Captain's Guest Room. The authenticity & value in one place. Walk to everything!
Bath
8.2 out of 10, Very Good, (21 reviews)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
The price is AED 349
AED 460 total
includes taxes & fees
24 May - 25 May
Captain's Guest Room. The authenticity & value in one place. Walk to everything!

Captain's House 1BR Apt. Walk to everything.

Captain's House 1BR Apt. Walk to everything.
Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
United States
Maryanne E.
The price is AED 349
AED 460 total
includes taxes & fees
25 May - 26 May
Captain's House 1BR Apt. Walk to everything.

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 579
AED 1,018 total
includes taxes & fees
25 May - 26 May
2 bedroom w/ expansive water 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 771
AED 1,329 total
includes taxes & fees
24 May - 25 May
Camp Forever 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 1,117
AED 2,140 total
includes taxes & fees
26 May - 27 May
Mere Point Sunrise Views at Eastern Shore!

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 884 total
includes taxes & fees
24 May - 25 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 771
AED 1,251 total
includes taxes & fees
2 Jun - 3 Jun
Fantastic Waterfront Views

30 Acres with Woodland Trails and Playground

30 Acres with Woodland Trails and Playground
Freeport
10.0 out of 10, Exceptional, (1 review)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
United States
Zoraida
30 Acres with Woodland Trails and Playground

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
31 May - 1 Jun
Centerview cottage

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,363 total
includes taxes & fees
3 Jun - 4 Jun
Full sized home

Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is AED 514
AED 1,797 total
includes taxes & fees
25 May - 26 May
Fully Updated Airy Historic Home in South Freeport

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, just like pictures "
United States
Evan M.
The price is AED 551
AED 1,121 total
includes taxes & fees
26 May - 27 May
South Portland Beach area rental

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"Incredible location right in downtown Freeport, and an even better host. We will definitely be staying with Jared again."
United States
Jake P.
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is AED 643
AED 1,025 total
includes taxes & fees
24 May - 25 May
Charming 1-bedroom ADU in wonderful Portland neighborhood

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2

Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
Brunswick
The price is AED 790
AED 1,694 total
includes taxes & fees
18 Jun - 19 Jun
Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2

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
7 Jun - 8 Jun
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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, (41 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,025
AED 1,782 total
includes taxes & fees
26 May - 27 May
Modern & Sunny House Steps from the Promenade. Private Parking!

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 826
AED 2,630 total
includes taxes & fees
2 Jun - 3 Jun
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

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 992
AED 1,700 total
includes taxes & fees
24 May - 25 May
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Captain's House 2BR Apt. The authenticity, great value, walk to everything.

Captain's House 2BR Apt. The authenticity, great value, walk to everything.
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 649
AED 804 total
includes taxes & fees
25 May - 26 May
Captain's House 2BR Apt. The authenticity, great value, walk to everything.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Bailey Island Hotel Reviews

Explore a world of travel with Expedia