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10 Oct - 12 Oct
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31 Oct - 2 Nov
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Featured Cottages in Bailey Island and around

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

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

10.0 out of 10, Exceptional, (48)
"Beautiful property and living space! Owners were very kind and helpful. Would highly recommend this spot to anyone!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (17)
"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
Exterior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (52)
"The cottage location was beautiful, we had a wonderful time on the beach. The cottage could have been a little more clean than it was, but after letting the property owner know she addressed those issues. "
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Outdoor dining

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

9.2 out of 10, Wonderful, (68)
"We loved the views and the morning walks to Grimes Cove and back. There can't be a better walk anywhere."
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 !!
Terrace/patio

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

9.8 out of 10, Exceptional, (34)
"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
Terrace/patio

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
Property grounds

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
Exterior

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
Property grounds

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
Exterior

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (7)
"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
Exterior

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.
Exterior

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

9.6 out of 10, Exceptional, (40)
"Peaceful, beautiful property. Perfect for our honeymoon. Highly recommend this place and Gurnet Trading Post for seafood!"
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Modern woodland privacy with ocean, trails, and lobster all in walking distance.
Property grounds

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
Exterior

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!
Exterior

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
Property grounds

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
Terrace/patio

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

10.0 out of 10, Exceptional, (9)
"This is a beautiful cabin right on a pond. The evening we arrived gave us a spectacular sunset. The cabin was comfortable and felt special, with lots of places to sit and enjoy coffee looking out at the pond. Kids had a great time running around. We hope to come back!"
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

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
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Property grounds

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
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
Outdoor dining

Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

9.8 out of 10, Exceptional, (38)
"My wife, daughter and I enjoyed staying at this property. We were able to take the stroller from the house and walk into the downtown area to restaurants etc…beautiful large deck at the property as well. Highly recommend!"
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"Whole hotel was immaculate. Frontt desk lady very helpful. Breakfast very good and ample. "
Lynn 1-night trip
Posted 1 day ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Bailey Island

Find out more about Bailey Island

Bailey Island Cottages information

Number of reviews
554
Accommodation
206 Cottages
Lowest Price
Highest Price

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