Book the Best Hotels with POOL in Bailey Island in 2026

Q: What are some accommodations with pools in Bailey Island?

The Westin Portland Harborview : Hotel located near Maine Mall. Offers free self parking, a pool, and complimentary wireless internet access. Clarion Hotel Portland Airport ME : Features a sauna, a pool, and complimentary bicycles. Cambria Hotel Portland Downtown-Old Port : Hotel located near Maine Mall. Offers a snack bar/deli, an indoor pool, and buffet. Portland Regency Hotel & Spa : Features a snack bar/deli, an indoor pool, and buffet. Portland Harbor Hotel : Features complimentary wired internet access, an indoor pool, and LCD televisions.

Bailey Island showing general coastal views

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

Check availability on Bailey Island Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Bailey Island hotels with a pool

Flagship Inn and Suites

Boothbay Harbor

Splash into summer at this Maine coastal retreat with a seasonal outdoor pool, terraced garden, and convenient in-town location.

CA $139 total

includes taxes & fees

Apr 1 - Apr 2

Spark by Hilton Portland Airport Maine Mall

South Portland

Slip into aquatic bliss with indoor and outdoor pools at this traveler-favorite hotel near Maine Mall and Portland Airport.

CA $90 total

includes taxes & fees

Mar 30 - Mar 31

Best Western Plus Brunswick Bath

Brunswick

Splash into aquatic bliss at this serene hotel with a year-round indoor pool experience.

CA $127 total

includes taxes & fees

Mar 14 - Mar 15

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

Sparkling indoor pool offers a serene escape in Portland's waterfront Art Deco hotel.

CA $147 total

includes taxes & fees

Apr 6 - Apr 7

Outdoor pool, a heated pool, open 9:00 AM to 10:00 PM, sun loungers

Best Western Merry Manor Inn

Highland

Dive into poolside paradise at this hotel featuring a relaxing waterfall hot tub and outdoor swimming oasis.

CA $136 total

includes taxes & fees

Mar 16 - Mar 17

The Harraseeket Inn & Event House Freeport Downtown

Freeport

Serene indoor pool and cozy fireside relaxation offer year-round bliss at this Freeport retreat.

CA $154 total

includes taxes & fees

Mar 15 - Mar 16

Germaine Inn South Portland

Thorton Heights

Dive into year-round aquatic bliss with heated indoor and outdoor pools, just steps from Maine Mall for shopping adventures.

CA $104 total

includes taxes & fees

Mar 19 - Mar 20

Fairfield Inn & Suites by Marriott Brunswick Freeport

Brunswick

Dive into the refreshing indoor pool at this Brunswick hotel, open all day for fitness or post-adventure relaxation.

CA $145 total

includes taxes & fees

Mar 22 - Mar 23

View all properties

Choose what matters most at hotels with a pool in Bailey Island

Breakfast included

4 stars

Top Bailey Island Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"Breakfast was good and hot Room was very clean Staff was very helpful Elevator floor could use some attention "

Clarion Hotel Portland Airport ME

4/10 Poor

"Breakfast doesn’t even start until 7. We had to leave before that. Many people stay for business and are gone by then. Also it was very cold and icy. The parking lot was pure ice and there was no salt or sand put down. We both almost landed on our faces and we had 2 children with us. "

Frequently asked questions

What are some accommodations with pools in Bailey Island?

The Westin Portland Harborview: Hotel located near Maine Mall. Offers free self parking, a pool, and complimentary wireless internet access. Clarion Hotel Portland Airport ME: Features a sauna, a pool, and complimentary bicycles. Cambria Hotel Portland Downtown-Old Port: Hotel located near Maine Mall. Offers a snack bar/deli, an indoor pool, and buffet. Portland Regency Hotel & Spa: Features a snack bar/deli, an indoor pool, and buffet. Portland Harbor Hotel: Features complimentary wired internet access, an indoor pool, and LCD televisions.

What is there to see and do in Bailey Island?

Make a point to visit attractions like Land's End Gift Shop. Discover sights such as Bailey Island Bridge, Mackerel Cove, and Cobwork Bridge during your stay.

When is the best time to book a hotel with a pool in Bailey Island?

Taking into account the local weather in Bailey Island can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Bailey Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia

Great Island Vacation Rentals

Book Hotels with a Pool in Bailey Island on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Bailey Island Hotels with a Pool