Search Cottages in Bailey Island

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 142 Cottages in Bailey Island with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (65)
"Our stay was amazing and everything was just as we expected, and more! Highly recommend this log cabin in the woods in quiet Maine"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

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

9.8 out of 10, Exceptional, (32)
"Such a cute cottage perfect for two couples. Sunrise and sunset on the deck was awesome. Great location and easy walk into town. We loved it!"
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

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

9.4 out of 10, Exceptional, (30)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"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
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer

Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer

8.8 out of 10, Excellent, (13)
"Nice views of tidal river "
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer
Charming 3BR, 1.5BA beachfront cottage with multi-level decks

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

9.2 out of 10, Wonderful, (31)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Two separate dog-friendly homes with water views & Linekin Bay Resort access

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
Private Contemporary Artist's Tree House on two acres with perennial gardens.
The floating two story private addition extends into the apple trees.

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

10.0 out of 10, Exceptional, (31)
"Very homey, very clean, comfortable bed. All we needed during our stay was procedez. The host was extremely responsive and courteous. We will like to visit again and I would stay here again."
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Classic Maine Beach Cottage **** Fabulous location!
Vibrant active local boating community

Classic Maine Beach Cottage **** Fabulous location!

9.2 out of 10, Wonderful, (24)
"Comfortable cottage with plenty of room. Very pleasant living space. We found it very convenient to the things we like to do, places we like to go. We would certainly come back"
The price is SAR 1,220
SAR 2,202 total
includes taxes & fees
3 Dec - 4 Dec
Classic Maine Beach Cottage **** Fabulous location!
Updated Long Island Maine Cottage
Interior

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay at Chaz' Long Island house. It is open and airy and maintains its 100 year old charm even as it's been updated. It sits in a great, grassy yard with plenty of bright light and has a terrific, large deck on the front. The golf cart ride to all beaches is short and lovely!"
Updated Long Island Maine Cottage
The Outlet House, Comfortable Cottage
Interior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (35)
"Nice clean quiet place but close to a lot of things."
The Outlet House, Comfortable Cottage
Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME
Marina

Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME

10.0 out of 10, Exceptional, (27)
"My sisters and I enjoyed our stay at this home, which is very comfortable, clean, and well stocked. Loved the rocking chairs looking out onto the water. Would definitely love to return some day."
Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME
As much "an experience" as shelter, Kinsale delights everyone of all ages.

As much "an experience" as shelter, Kinsale delights everyone of all ages.

9.2 out of 10, Wonderful, (13)
"Fantastic !!!"
As much "an experience" as shelter, Kinsale delights everyone of all ages.
Quaint Retro Ash Cove Cottage
Room

Quaint Retro Ash Cove Cottage

9.6 out of 10, Exceptional, (15)
"a 12 on a 1=10 scale. Real Maine...void of pretense and dreaded pandemic migrants...wonderful folks own the property. "
Quaint Retro Ash Cove Cottage
A Cozy Retreat on Southport Island
Periwinkle Cottage with a porch facing the ocean

A Cozy Retreat on Southport Island

9.8 out of 10, Exceptional, (25)
"Adorable spot. Classic and cozy seaside cottage with the amazing boat house as an extra bonus. We walked to Robinson’s Wharf every night. Delish! We wanted to stay longer, oh well, next time! "
A Cozy Retreat on Southport Island
Cozy cottage fully renovate with open concept on Forest Lake close to I95
Exterior

Cozy cottage fully renovate with open concept on Forest Lake close to I95

10.0 out of 10, Exceptional, (1)
"The little “camp” was spotless, the decor modern and impressive, attention to every detail and comfort well-thought out, and amenities numerous. There were cozy spots for reading or gazing out at the lake. The deck allowed for serious star-gazing. The location is quiet, yet a short drive from bustling Portland or quieter towns. I enjoyed kayaking on the lovely, clear, clean lake, as well as long walks on the camp roads. Check-in/checkout was a breeze. An idyllic getaway!!"
Cozy cottage fully renovate with open concept on Forest Lake close to I95
Charming Southport Island Cottage on Cozy Harbor with Sunny Deck - Sleeps 6!
Exterior

Charming Southport Island Cottage on Cozy Harbor with Sunny Deck - Sleeps 6!

Charming Southport Island Cottage on Cozy Harbor with Sunny Deck - Sleeps 6!
Boothbay - Ocean Point home w/ screened porch, amazing view & water access

Boothbay - Ocean Point home w/ screened porch, amazing view & water access

9.2 out of 10, Wonderful, (21)
"Peaceful with amazing views!"
Boothbay - Ocean Point home w/ screened porch, amazing view & water access
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, (1)
"Great property, great host, just as described."
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Woodbine Cottage, The Heart Of Harpswell
View from the water side

Woodbine Cottage, The Heart Of Harpswell

2.0 star property
9.8 out of 10, Exceptional, (9)
"Our stay for my Birthday weekend was very nice. The cottage was very clean and the well stocked kitchen made cooking easy. Our bed was the most comfortable we have ever slept on at a cottage. The location was perfect for taking wonderful hikes every day. Anne met us at the cottage after our long trip and was wonderful to show us around the cottage and its amenities. Would highly recommend this Cottage as the best we have ever stayed at. "
Woodbine Cottage, The Heart Of Harpswell
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.
Don't see what you're looking for?
See all available properties in Bailey Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Bailey Island

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
THE GILLS GROUP has two additional cottages available for larger groups

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"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
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

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

9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist

10.0 out of 10, Exceptional, (35)
"Beautiful place , had everything you need . Very comfortable bed . Great shower & Kitchen . Also a great location! "
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
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.

Frequently asked questions

Why book your cottage in Bailey Island with Expedia?
We think that vacations should be a breeze, so if you’re in search of cottages in Bailey Island at a great price, Expedia has you covered. Stick to the budget and choose a cheap option far away from the downtown buzz, or splurge on a 5-star cottage to spoil your favorite people.
How can I find cheap cottages in Bailey Island?
A good way to spot cheap cottages in Bailey Island is with Expedia’s handy filter tool. Refine your search results by amenities, budget and star rating to land unbeatable rates in just a few keystrokes.