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Featured Cottages in Bailey Island

Our top choices for Bailey Island cottages

Private Contemporary Artist's Tree House on two acres with perennial gardens.

10.0 out of 10, Exceptional, (48)
"Beautiful, fun space. Very comfortable, and accommodating. Great location and hosts!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (16)
"Lovely location, quiet, serene, and the cottage is totally cute and comfortable. "
Enjoyable 1-bedroom rustic cottage in Southport.

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"This cozy cottage is in the beautiful town of Phippsburg, next to the break-taking beach of Popham State Park. With its site on the ocean shore, the sound of waves soothes your soul, and the beach lends all kinds of opportunities for exploring both at low tide and high tide. Our host and hostess were very responsive to our needs, and my daughter and I greatly enjoyed out stay."
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.2 out of 10, Wonderful, (68)
"Must stay! We loved it and the location. Very relaxing and the neighborhood is very safe to walk around and explore. The house offers everything you would need with the best views. My family would definitely stay there again!"
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!

9.8 out of 10, Exceptional, (33)
"Clean, cute cottage for four on a steep waterfront lot with a beautiful vista. Nice kitchen for exended stay. Great fireplace."
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views. New Listing !!

Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

8.8 out of 10, Excellent, (21)
"Very beautiful and easy to communicate with the property management "
Ocean Watch - Relax and let the ocean sweep you away at this charming retreat

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

9.4 out of 10, Exceptional, (25)
"Great little cabin that provided everything needed for my family! Plenty of games and activities for the kids! Great quiet and secluded location and the screed in porch provided a nice refuge at night!"
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities

2.0 star property
10.0 out of 10, Exceptional, (9)
"Great property, great host, just as described."
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities

Oceanfront Escape: Deck & Granite Steps to Shore

9.4 out of 10, Exceptional, (3)
"Everything was beautiful and we loved our stay!"
Oceanfront Escape: Deck & Granite Steps to Shore

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage

Popham Beach Direct Oceanfront Cottage Steps to the sand

9.8 out of 10, Exceptional, (67)
"So relaxing!! "
Popham Beach Direct Oceanfront Cottage Steps to the sand

Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

9.6 out of 10, Exceptional, (40)
"We had a great time! We never saw the tide drain completely out to forage though, I was looking forward to that. The location is perfect with a lovely deck. Bring bug spray, mosquitoes are super thick, assuming from all of the rain we had. The pull out sofa is not really usable due to a bar at the top that sticks in your ribs. Kitchen was fully equipped and loved having a dishwasher. Owners and/or management were very responsive with a couple of issues that arose. We unfortunately had to leave a...
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.

Modern woodland privacy with ocean, trails, and lobster all in walking distance.

10.0 out of 10, Exceptional, (50)
"My friend and I felt very relaxed at this house. The beds were comfortable and the kitchen was stocked with most every cooking equipment needed. The host answered any question I had very quickly and supplied information about the surrounding area. It was a great place to unwind!"
Modern woodland privacy with ocean, trails, and lobster all in walking distance.

Waterfront Cottage

9.4 out of 10, Exceptional, (33)
"The cottage is in a great location to sit and linger over a cup of coffee in the morning, looking out at the water. It is close to the Maine Maritime Museum and the town of Bath."
Waterfront Cottage

Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!

10.0 out of 10, Exceptional, (13)
"Wonderful stay! comfortable cozy and cute, tidy cottage. Hosts are responsive and welcoming. Cottage is very well thought out and location is great. Would love to stay again!"
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.6 out of 10, Exceptional, (18)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

10.0 out of 10, Exceptional, (9)
Charming Cottage on the Great Pond in Boothbay Harbor, Maine

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (104)
"Fabulous location for a multi generational family gathering. We had a wonderful time."
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Beachy Vibes Only !! Updated Oceanfront Gem for 2

9.8 out of 10, Exceptional, (51)
"Absolutely wonderful accommodations. Very relaxing and peaceful surroundings. Everything was top notch."
Beachy Vibes Only !! Updated Oceanfront Gem for 2

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

2.0 star property
9.6 out of 10, Exceptional, (7)
"Perfect getaway for three adults. The weather cooperated so we were able to enjoy the lake and spent most of the weekend outside. The location is great and easy to access. The home is comfortable, camp style living. It could benefit from an updated living room chair, as the one there is missing any solid cushioning. The loft area is tight and not suitable for adults. Amenities are simple and neighbors are very close — albeit friendly, overall good stay and would return. "
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
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

Find out more about Bailey Island

Find out more about Bailey Island

Bailey Island Cottages information

Number of reviews
579
Accommodation
205 Cottages
Lowest Price
Highest Price