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Featured Cottages in Bailey Island

Property grounds
Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor
9.8 out of 10, Exceptional, (39)
"Serene and private with an amazing view. Highly recommend!"
Southport Island Cottage | Deck & New Luxe Kitchen | Near Boothbay Harbor
View from property
Popham Beach Direct Oceanfront Cottage Steps to the sand
10.0 out of 10, Exceptional, (44)
"We had a great stay. Check in and communication was easy. Due to storm damage, our original booked cottage was not available and Deb offered us a different (much larger) home without added cost. We greatly appreciated it so we didn't have to cancel our vacation. The home was very clean and had everything we needed and then some. The area is beautiful and the beach was very clean. You cannot beat the views from the home. We look forward to staying here again!"
Popham Beach Direct Oceanfront Cottage Steps to the sand
Fridge, microwave, oven, stovetop
Waterfront Cottage
9.4 out of 10, Exceptional, (14)
"Clean, nicely decorated and stocked, and located right on the water with 180 degree views of tidal inlet. Should have brought binoculars to bird watch."
Waterfront Cottage
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Pool
Island cottage getaway
10.0 out of 10, Exceptional, (12)
"Coastal funky cottage, very comfortable and clean, terrific location and fabulous porch!"
Island cottage getaway
Highland Lakefront Cabin
9.0 out of 10, Wonderful, (64)
"Beautiful view. Worked for what we needed."
Highland Lakefront Cabin
Fridge, microwave, oven, stovetop
Dog-friendly forest cottage with HOA beach on Linekin Bay, walk to dining/spa
9.0 out of 10, Wonderful, (2)
"A terrific cozy cabin for a getaway with our dogs. The property was in a good location, close to town, with ample yard to explore wiwith the pups. The cabin was cozy and comfortable."
Dog-friendly forest cottage with HOA beach on Linekin Bay, walk to dining/spa
Outdoor spa tub
Private Contemporary Artist's Tree House on two acres with perennial gardens.
10.0 out of 10, Exceptional, (15)
"What an enjoyable and relaxing respite! The location was quiet & private but a quick drive to restaurants, sites & attractions. Best of both worlds. Our host (Brian) was friendly and gracious. He made sure we had everything we needed and was a joy to talk to. This property is definitely worth returning to!"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Fridge, microwave, oven, stovetop
The Outlet House, Comfortable Cottage
9.6 out of 10, Exceptional, (28)
"Clean, comfortable, very well located. We have stayed here several times."
The Outlet House, Comfortable Cottage
Property grounds
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
Exterior
Boothbay privacy with the ocean, lake, trails, and lobster, all within a walk.
10.0 out of 10, Exceptional, (35)
"This was a perfect getaway for us. The home was lovely and very clean. Had everything we could need/want including a sweet welcome gift from the owners. Home is exactly as described and pictured. Location is convenient to everything in the area. We gave 4 stars for location only because we couldn't walk the neighborhood as there aren't sidewalks and it's a somewhat busy road. But having said that there are endless trails and paths everywhere to walk. We visited a different one every day and...
Boothbay privacy with the ocean, lake, trails, and lobster, all within a walk.
Fridge, microwave, oven, stovetop
Renovated waterfront cabin with beach access, canoes, WiFi, & full kitchen
9.4 out of 10, Exceptional, (3)
"Map quest and google take you on unnecessary routes into the cabin. We got there in the dark and after being instructed to drive into the woods on dirt road we came into someones back yard. Noticed one small sign nailed to post pointing in "assumed" direction to go. No lights, very dark and even when we found the house no lights were left on or hey how about a solar night light over the door?. Need a welcome book too listing what's what and where inside items are located"
Renovated waterfront cabin with beach access, canoes, WiFi, & full kitchen
Interior
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.8 out of 10, Excellent, (43)
"We needed a quiet place to visit with elderly aunt and uncle. This was a great place with all the living space on the same floor with spacious area to visit."
Unique oceanfront home with a deck, tons of natural light, & amazing views
TV, fireplace, books, stereo
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.4 out of 10, Exceptional, (22)
"Beautiful home that is a great proximity to Boothbay Harbor downtown. The pond is very nice but the water level was very low during our stay in March and there were no boats available as described in the listing. It is unclear whether this is something to note for all offseason travelers"
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Interior
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
10.0 out of 10, Exceptional, (47)
"Popham Beach is amazing! As a busy professional, I have needed some time to relax and recharge. Although the weather wasn’t as cooperative as I hoped, being rather cold and windy the first days and rainy on the third, it meant I had the beach basically to myself each day when I ventured out. Not spending all day on the beach also gave me time to visit some of the nearby attractions, such as Fort Popham, the Maine Maritime Museum, the Botanical Gardens, and the Wiscasset Antiques Mall. I highly...
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Property grounds
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
9.4 out of 10, Exceptional, (9)
"When we walked in, all we could say was WOWWWWW!!!! It was beautiful. Everything was clean and absolutely met all expectations and more!"
Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home
Beach
Two separate dog-friendly homes with water views & Linekin Bay Resort access
8.0 out of 10, Very good, (5)
"This was a beautiful place to stay and had more parking than we expected. The only hiccups we had was that the check in code we were given was one digit off from what it actually was so we had a little trouble getting into the house. Also there is an outlet that was uncovered in the bedroom and we had a child touch it. Luckily the child wasn’t harmed but this should definitely be addressed if there’s any little ones staying on the property. The houses were very clean and the only reason I gave...
Two separate dog-friendly homes with water views & Linekin Bay Resort access
Fridge, microwave, oven, stovetop
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
10.0 out of 10, Exceptional, (10)
"Absolutely loved our late summer stay at this dreamy cottage in Harpswell. The cottage reminded us of childhood summer stays in coastal New England and the nostalgia was real and definitely welcome."
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
TV, DVD player
The Little House - Gorgeous Views of Lowell's Cove and Casco Bay
9.8 out of 10, Exceptional, (7)
"The Little House is situated in a great spot which provides for a lovely view of the water. It was very clean and I really appreciate the hosts using a professional laundering service for sheets and towels - provides reassurance of sanitary conditions during this unfortunate time of Covid. The home is well maintained. Three things which impacted our stay adversely: the queen bed is quite hard, like a brick; very uncomfortable. The living room has a small couch. Unfortunately it could really...
The Little House - Gorgeous Views of Lowell's Cove and Casco Bay
Beach
Your own private island! Rustic and close to Nature.
9.4 out of 10, Exceptional, (30)
"My husband and myself have spent multiple years returning to the island. We really highly recommend it for the rustic nature loving souls who are searching for some serious separation from chaos. Deb and her husband are also just wonderful to work with. A tree had fallen in the pathway and her husband drove a long distance to come cut it out of the way and even found me on the island to ask if we were okay with the way he had moved and cut the tree. Just a wonderful family. We spend much of...
Your own private island! Rustic and close to Nature.
Don't see what you're looking for?
See all available properties in Bailey Island
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.

Other property types in Bailey Island

Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Fridge, microwave, oven, stovetop
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is NZ$669
includes taxes & fees
19 May - 20 May
Completely remodeled 2 bedroom apartment in Portland's West End
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.

Bailey Island Cottages information

Number of reviews
435
Accommodation
127 Cottages
Lowest Price
Highest Price

Recent Reviews in Bailey Island
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