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Compare 179 Cottages in Bailey Island with updated reviews, rates, and availability.

Popham Beach Direct Oceanfront Cottage Steps to the sand

9.8 out of 10, Exceptional, (58)
"Great location and very clean Camp with great views. "
Popham Beach Direct Oceanfront Cottage Steps to the sand

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (100)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

10.0 out of 10, Exceptional, (9)
"This place has a ton of character and we loved being able to walk to restaurants, the park, and private beach. Great view from the porch!"
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Waterfront Cottage

9.2 out of 10, Wonderful, (24)
"Perfect for us close location wise for visiting my so at college, close to freeport for shopping, house was so comfortable and had amazing views. Everything you needed was supplied, cant wait to visot again"
Waterfront Cottage

Cute 2+ Bedroom Cottage

9.6 out of 10, Exceptional, (14)
"Returned this year for our 2nd stay. Clean, comfortable and quiet. Will book again!"
Cute 2+ Bedroom Cottage

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

9.8 out of 10, Exceptional, (18)
"Very nice all the basics covered. Close to the harbor, very quiet."
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (39)
"We booked this to be near our daughter and grandchildren in Freeport. It is a great location, large interior, quiet location."
The Outlet House, Comfortable Cottage

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

9.8 out of 10, Exceptional, (32)
"I highly recommend this place for ocean lovers and only a 10 minute walk to the harbor"
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

Boothbay Harbor Cottage Overlooking Mill Cove

10.0 out of 10, Exceptional, (18)
"Very cozy and clean cottage with easy walk to town"
Boothbay Harbor Cottage Overlooking Mill Cove

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

9.8 out of 10, Exceptional, (6)
"A rustic quaint adorable house. Great views of the water--everything was on the small size, but really do you need anything more?"
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

9.4 out of 10, Exceptional, (33)
"Very cozy house in an absolutely lovely spot. We really enjoyed the outdoor space and the peace and quiet. "
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

Classic Maine Beach Cottage **** Fabulous location!

9.2 out of 10, Wonderful, (25)
"Great stay at a cute property"
The price is AED 1,469
AED 2,518 total
includes taxes & fees
15 May - 16 May
Classic Maine Beach Cottage **** Fabulous location!

Cozy Year-round House right outside Portland Maine on Highland Lake.

9.8 out of 10, Exceptional, (62)
"We really enjoyed our stay. The location couldn’t be any better and the host was very attentive. We would consider staying again. "
Cozy Year-round House right outside Portland Maine on Highland Lake.

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

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

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

Historic riverfront home with boathouse & private dock - dogs OK

8.8 out of 10, Excellent, (20)
"Very close to botanical garden and harbor. Perfect for our needs."
Historic riverfront home with boathouse & private dock - dogs OK

Boothbay privacy with the ocean, lake, trails, and lobster, all within a walk.

10.0 out of 10, Exceptional, (41)
"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!"
Boothbay privacy with the ocean, lake, trails, and lobster, all within a walk.

Beachy Vibes Only !! Updated Oceanfront Gem for 2

9.8 out of 10, Exceptional, (45)
"This was the perfect little Maine cabin getaway! Wonderful location right on the water that offered endless wildlife and beautiful views. Great location close to town if you needed anything but perfectly quiet and peaceful at the cabin. "
Beachy Vibes Only !! Updated Oceanfront Gem for 2

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

10.0 out of 10, Exceptional, (8)
"Location is great, clean cabin with all you need, privacy, access to food and fun. Comfortable feeling as you enter cabin views of waterfront community , with beautiful sunsets on the harbour. "
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
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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Other property types in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (212)
"We enjoyed everything about our place!"
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (1)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
The price is AED 637
AED 1,575 total
includes taxes & fees
1 May - 2 May
Orchid Harbor, Bailey Island 3BR

The Weldon Hotel

4.0 star property
9.8 out of 10, Exceptional, (56)
"Great hotel"
The price is AED 772
AED 1,117 total
includes taxes & fees
11 May - 12 May
The Weldon Hotel
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.