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Browse Select Bailey Island Cottages

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

10.0 out of 10, Exceptional, (47)
"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.

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (41)
"We loved our stay here! The cottage was super clean and in a quiet area within walking distance to town and all the shops and restaurants. Check-in was simple and the hosts were very friendly and responded quickly. Would definitely stay again!"
The Outlet House, Comfortable Cottage

Boothbay Harbor Cottage Overlooking Mill Cove

9.8 out of 10, Exceptional, (19)
"Clean, close to downtown."
Boothbay Harbor Cottage Overlooking Mill Cove

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi

8.0 out of 10, Very good, (1)
"House was very clean with the exception of some dust/sand on floors, even though you could not see it walking on the floors in bare feet always felt that that maybe a good washing was needed. We just swept with the broom/vacuum and it was better. But one thing that really stood out when arriving is the cement stairs dug into the hill that you needed to go down to get to the house. So glad that there was a railing to hold onto because the stairs were not level at all. This posed a real threat to...
Quiet 3-bedroom cottage w/ 2 specious deck with water views in Brunswick w/ WiFi

Enjoyable 1-bedroom rustic cottage in Southport.

10.0 out of 10, Exceptional, (9)
Enjoyable 1-bedroom rustic cottage in Southport.

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

10.0 out of 10, Exceptional, (12)
"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!

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

10.0 out of 10, Exceptional, (6)
Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Charming 3BR, 1.5BA beachfront cottage with multi-level decks

9.2 out of 10, Wonderful, (36)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks

Cozy Cottage with stunning views of Stover's Cove.

9.6 out of 10, Exceptional, (5)
"We loved our time at the Cozy Cottage. They have the space well stocked with laundry detergent, dish soap, and even toiletries! All the communication was smooth and fast replies. I would recommend staying here if you are visiting Harpswell! "
Cozy Cottage with stunning views of Stover's Cove.

Lilac Cottage - Near Georgetown Island - Midcoast Maine

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay at this property. Our dogs loved being able to chase eachother around the yard"
Lilac Cottage - Near Georgetown Island - Midcoast Maine

Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village

9.4 out of 10, Exceptional, (9)
"Incredible views!"
Charming Cottage: Deepwater Dock, Panoramic Linekin Bay Views, Near Village

Your own private island! Rustic and close to Nature.

9.4 out of 10, Exceptional, (32)
"wonderful place, glamping, wildlife all around, you can't but enjoy the beauty of Mid Coast Maine. Thanks for sharing your island with all of us !"
Your own private island! Rustic and close to Nature.

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (57)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (68)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (18)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage

Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!

10.0 out of 10, Exceptional, (1)
"We had a blast! The house was perfectGreat viewsVery relaxing "
Enjoy Stunning Ocean Views & Coastal Access at Sea Mist Overlook!

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

9.6 out of 10, Exceptional, (17)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (102)
"We sat and watched a major winter storm outside the window. Very exciting from within a cozy house. We enjoyed staying in a house where you could feel somebody's presence, rather than the "accessorized" vacation homes with welcoming signs from the Dollar store etc. Only thing lacking--place needs a new key box because the existing one is hard enough to use that it feels like it won't work. Gorgeous place!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Come and enjoy our Boothbay Cottage

10.0 out of 10, Exceptional, (48)
"We had a great second stay at this location. Very clean and enjoyed the trip! "
Come and enjoy our Boothbay Cottage
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