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Featured Cottages in Bailey Island

Seawood Sunset Cottage: Southport Island
Seawood Sunset Cottage: Southport Island
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
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
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The Outlet House, Comfortable Cottage
9.6 out of 10, Exceptional, (29)
"Comfortable Cottage is a great description of this home! We enjoyed our time there and appreciated the location. It was very clean. We’ll definitely stay again!"
The Outlet House, Comfortable Cottage
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!
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
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
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
9.8 out of 10, Exceptional, (27)
"Just got back to NYC after spending 3 nights at the house with my dog. I already miss it. It's practically on top of the water, and sits in a very private, quiet and secluded location on a heavily wooded lot. It's a bit off the beaten path, but still a relatively short drive (10-30 mins, depending) to anywhere within the Harpswell/Brunswick area. Comfortable bed and furniture. The outdoor furniture seemed brand new (Adirondack chairs). It's a very cozy house that's perfect - even spacious - for...
Laurel Shore Cottage with Seasonal Private Tidal Dock, Pet friendly.
Island cottage getaway
10.0 out of 10, Exceptional, (15)
"Lovely stay with family as the island was just opening up and getting ready for the season. Beautiful porches and spaces for relaxation and calm and fun!"
Island cottage getaway
Highland Lakefront Cabin
9.0 out of 10, Wonderful, (65)
"We had a very nice stay and enjoyed both the cottage and property. It was a bit rainy, so we didn't get a chance to enjoy the fire pit area, but it looked great. There are a few places that could use some updates, but this is a true lake cottage, so it's really like elevated camping."
Highland Lakefront Cabin
Waterfront Cottage
9.4 out of 10, Exceptional, (15)
"This cozy cottage on a quiet lane has a beautiful view of the water. We saw a multitude of water fowl. The landtrust area just down the road made for beautiful morning walks with many birds and deer to keep you company. The neighbors were friendly and the host was responsive and helpful."
Waterfront Cottage
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.
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
10.0 out of 10, Exceptional, (1)
"The cottage was recently updated and everything worked great. The beds were super comfy. It has a cute little deck too. The owners live close by and were very friendly and helpful. We'd love to visit again!"
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
As much "an experience" as shelter, Kinsale delights everyone of all ages.
10.0 out of 10, Exceptional, (7)
"We absolutely loved this house!! The view was incredible so we spent a lot of time on the porch and exploring the water. The house was spacious and felt like a classic coastal Maine getaway. We would absolutely love to return next summer!"
As much "an experience" as shelter, Kinsale delights everyone of all ages.
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
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
9.4 out of 10, Exceptional, (23)
"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
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer
8.0 out of 10, Very good, (8)
"Property was wonderful. Very comfortable and clean. Working with the management company was not a good experience. I received multiple e-mails and texts from them providing me with confirmation of my trip, trip details, early check in etc.....Not one of those communications indicated that they still needed my ID verified. Once I sent my ID for verification on the day of my checkin and it was accepted and confirmed on line, my reservation was cancelled by the management group because they could...
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay
9.4 out of 10, Exceptional, (6)
"Cozy and comfortable"
Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
10.0 out of 10, Exceptional, (48)
"The facility and the location met our expectations, the price for two nights was a bit steep. Loved the proximity to the beach!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
9.2 out of 10, Wonderful, (10)
"LOVED my little house on the water! It was the perfect size and everything was just what I needed. I will 100% be staying there again on any future visits. That being said, the bathroom would not be ideal for anyone in the 6' range. I am 5'6" and was a little cramped. I imagine anyone taller or who has claustrophobia would not be super pleased. I doubt they would be able to do anything different without MAJOR reconstruction so it is what it is for the size they had to work with. It was totally...
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
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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

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
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, (33)
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
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
348
Accommodation
150 Cottages
Lowest Price
Highest Price

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