Search Cottages in Bailey Island

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

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

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

8.8 out of 10, Excellent, (14)
"Our family had a great stay here. Lovely location."
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer
Salty Breeze Cottage
Fridge, microwave, oven, stovetop

Salty Breeze Cottage

10.0 out of 10, Exceptional, (6)
"We absolutely loved this peaceful spot by the water! It’s a quiet location with great water access, and the property is very well managed and maintained. We’d love to return!"
Salty Breeze Cottage
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

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

9.8 out of 10, Exceptional, (26)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
The Outlet House, Comfortable Cottage
Fridge, microwave, oven, stovetop

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
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Interior

Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town

9.6 out of 10, Exceptional, (25)
"Convenient and cozy. Lovely wooded lot with views. "
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

Enjoyable 1-bedroom rustic cottage in Southport.
Cute 2+ Bedroom Cottage
Fridge, microwave, oven, stovetop

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

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

9.6 out of 10, Exceptional, (66)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Exterior

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.0 out of 10, Wonderful, (64)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Beach

WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND

10.0 out of 10, Exceptional, (1)
"Boomfish Cottage is a cozy place with everything you could need . It was clean , comfy and serene . It provided the perfect calm for us during a weekend long family wedding at nearby Caswell Flower Farm . It was also easy access for an older person ( me) as well as small children and my little ShihTzu rescue dogs . My granddaughters came by and loved catching minnows in the still warm lake. Extra bonus was enjoying the peak foliage at the lake . Eric , the property manager was very communicative...
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Fridge, microwave, oven, stovetop

Thorburn - Experience a classic ME vacation at this beautiful summer cottage

9.8 out of 10, Exceptional, (13)
"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
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
TV, DVD player, books, video library

Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor

9.8 out of 10, Exceptional, (43)
"Great spot in Southport Island. Highly recommend."
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Terrace/patio

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

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
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Interior

Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great property, great host, just as described."
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (50)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior

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

8.6 out of 10, Excellent, (53)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views
Popham Beach Direct Oceanfront Cottage Steps to the sand
Interior

Popham Beach Direct Oceanfront Cottage Steps to the sand

10.0 out of 10, Exceptional, (62)
"Great location and very clean Camp with great views. "
Popham Beach Direct Oceanfront Cottage Steps to the sand
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Outdoor spa tub

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

10.0 out of 10, Exceptional, (32)
"Great stay. Unique place with lots of character. Clean and pleasant. Loved the geese that greeted us each time we walked in/out (fenced not loose) !"
Private Contemporary Artist's Tree House on two acres with perennial gardens.
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Terrace/patio

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Bailey Island with Expedia?
We think a getaway should be simple, so if you’re in search of cottages in Bailey Island at a competitive rate, Expedia has got your back. Keep costs down and opt for an economical option far from the rush of the city, or book a 5-star cottage to really pamper your favorite people.
How can I find cheap cottages in Bailey Island?
With Expedia’s useful filter tool, booking cheap cottages in Bailey Island has never been simpler. To discover properties that are friendly on the wallet, refine your search results by amenities, star rating and budget.