Search Vacation Homes in Bailey Island
Change your mindBook hotels with free cancellation
Be pickySearch 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
Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BRHarpswell
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."
Karen T.
The price is AED 637
AED 1,563 total
includes taxes & fees
16 Jun - 17 Jun
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! "
Nina P.
The price is AED 384
AED 498 total
includes taxes & fees
21 Jun - 22 Jun
Captain's House 1BR Suite. Walk to everything. Large yard. Pets welcome!
Captain's House 1BR Suite. Walk to everything. Large yard. Pets welcome!Bath
7.6 out of 10, Good, (14 reviews)
"We stayed for two nights. Good location."
Maryanne E.
The price is AED 489
AED 613 total
includes taxes & fees
11 Jun - 12 Jun
Mid Coast Getaway w/ water views
Mid Coast Getaway w/ water viewsWest Point
9.4 out of 10, Exceptional, (6 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
chuck c.
The price is AED 405
AED 813 total
includes taxes & fees
14 Jun - 15 Jun
Charming 1-bedroom ADU in wonderful Portland neighborhood
Charming 1-bedroom ADU in wonderful Portland neighborhoodBack Cove
The price is AED 643
AED 1,017 total
includes taxes & fees
11 Jun - 12 Jun
South Portland Beach area rental
South Portland Beach area rentalWillard Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, just like pictures "
Evan M.
The price is AED 686
AED 1,293 total
includes taxes & fees
15 Jun - 16 Jun
The price is AED 519
AED 1,775 total
includes taxes & fees
16 Jun - 17 Jun
Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2
Walk to town, 200yr-old 4BR house adjacent to Bowdoin campus! #2Brunswick
The price is AED 1,074
AED 2,064 total
includes taxes & fees
18 Jun - 19 Jun
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.
Find vacation rentals that suit your style
Aparthotels
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Bailey Island Hotel Reviews
Holiday Inn Portland-By the Bay by IHG
10/10 Excellent
