Search Cottages in Bailey Island
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 179 Cottages in Bailey Island with updated reviews, rates, and availability.

Popham Beach Direct Oceanfront Cottage Steps to the sand
Popham Beach Direct Oceanfront Cottage Steps to the sand
9.8 out of 10, Exceptional, (58)

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (100)

Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!
10.0 out of 10, Exceptional, (9)

Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Waterfront Cottage
Waterfront Cottage
9.2 out of 10, Wonderful, (24)

Cute 2+ Bedroom Cottage
Cute 2+ Bedroom Cottage
9.6 out of 10, Exceptional, (14)

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
9.8 out of 10, Exceptional, (18)

The Outlet House, Comfortable Cottage
The Outlet House, Comfortable Cottage
9.8 out of 10, Exceptional, (39)
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
Other property types in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (212)

Orchid Harbor, Bailey Island 3BR
Orchid Harbor, Bailey Island 3BR
10.0 out of 10, Exceptional, (1)
The price is AED 637
AED 1,575 total
includes taxes & fees
1 May - 2 May

The Weldon Hotel
The Weldon Hotel
9.8 out of 10, Exceptional, (56)
The price is AED 772
AED 1,117 total
includes taxes & fees
11 May - 12 May
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.
Recent reviews of Bailey Island hotels
Recent reviews of Bailey Island hotels

Holiday Inn Portland-By the Bay by IHG
5/5 Excellent
"Had a very positive experience staying here for 3 days! Hotel is very close to the State Theater & the Portland Art Museum. Also lots of good restaurants around the block. Staff was very nice and friendly!!! Breakfast was divine :-) There is construction going on but it did not bother us. I thought they were very quiet when we were there."
A verified traveler stayed at Holiday Inn Portland-By the Bay by IHG
Posted 13 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in Bailey Island
- Vacation Homes in Bailey Island
- Apartments in Bailey Island
- Condo Rentals in Bailey Island
- Cabin Rentals in Bailey Island
- B&B in Bailey Island
- Lodges in Bailey Island
- Motels in Bailey Island
- Guest Houses in Bailey Island
- Farmstay in Bailey Island
- Aparthotels in Bailey Island
- RV Parks in Bailey Island
- Inns in Bailey Island
- Resorts in Bailey Island
- Villas in Bailey Island
- Hotels