Book the Best Hotels with POOL in Bailey Island in 2026

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

Quality Inn & Suites South Portland : Hotel located near State Theatre. Provides free self parking, a pool, and complimentary wireless internet access. Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel : Hotel located near Maine Mall. Features an indoor pool, an outdoor pool, and daily. Clarion Hotel Portland Airport ME : Features a seasonal outdoor pool, an indoor pool, and a sauna. Clarion Pointe South Portland : Hotel, 4-minute walk from Cross Insurance Arena. Provides a sauna, a pool, and complimentary bicycles. Portland Harbor Hotel : Hotel located near State Theatre. Features buffet, a seasonal outdoor pool, and complimentary wireless internet access.

A rocky shoreline with a boat, a house, and a forest in the background.

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

An indoor swimming pool with a clear water surface, surrounded by beige tiled walls and a blue accent wall.

1. Holiday Inn Express Hotel & Suites Freeport by IHG

Freeport

Serene indoor pool sanctuary in Freeport awaits with extended hours for swimming and relaxation near popular attractions.

CA $142 total

includes taxes & fees

Nov 2 - Nov 3

A swimming pool with clear blue water, surrounded by large windows offering views of trees and a clear sky.

2. Hampton Inn Freeport/Brunswick

Freeport

Dip into year-round pool fun at this hotel with a sparkling indoor swimming sanctuary.

CA $149 total

includes taxes & fees

Nov 8 - Nov 9

An indoor swimming pool with clear signage, including pool user capacity and no diving rules.

3. SpringHill Suites by Marriott Freeport Brunswick

Freeport

Plunge into relaxation at the indoor pool, where comfort meets convenience in this modern Freeport hotel near shopping gems.

CA $122 total

includes taxes & fees

Nov 2 - Nov 3

A modern living room with dark blue walls, large windows, and a view of a landscaped garden.

4. Best Western Freeport Inn

Freeport

Sun-soaked summer splashing awaits at this peaceful inn with a seasonal outdoor pool.

CA $134 total

includes taxes & fees

Nov 3 - Nov 4

A hotel room with a large bed, a desk with a chair, a TV, and a window with curtains.

5. Hilton Garden Inn Freeport Downtown

Freeport

Dive into a refreshing aquatic escape at this Freeport hotel with an inviting indoor pool.

CA $161 total

includes taxes & fees

Nov 8 - Nov 9

A swimming pool with lounge chairs and tables, surrounded by walls with wooden panels and windows.

6. 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 $167 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool with a lifeguard chair, a blue chair, and a pool ladder.

7. Best Western Plus Brunswick Bath

Brunswick

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

CA $143 total

includes taxes & fees

Nov 24 - Nov 25

An indoor swimming pool with lounge chairs and a view of the outdoors.

8. The Harraseeket Inn & Event House Freeport Downtown

Freeport

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

CA $197 total

includes taxes & fees

Nov 1 - Nov 2

View all properties

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

Breakfast included

4 stars

Top Bailey Island Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent

"staff is friendly rooms are clean. Bathrooms are clean good price."

Portland Regency Hotel & Spa

10/10 Excellent

"I chose to take a day and night for me. Booked day of.. based on proximity, price (via Hotels.com), and did I get a good “vibe”. I do not regret my descision one but smiling walking in Monday. Walked out Tuesday, after a pit stop at the spa (incredible massage), with an even bigger smile. I scheduled a follow up massage the next day for the next Tuesday. Now, do I stay again this Monday? 🤔"

Ramada Plaza by Wyndham Portland

8/10 Good

"I was there for 2 nights and was told when I checked in housekeeping would not be cleaning my room but if I needed anything just ask. I was fine with that. Room was clean, bed was comfortable, and there was a fridge in the room. The shower head was adjustable for different water flows but the pressure made them all seem about the same. The shower covering over the old tub felt weird as there was some give to the floor as you moved around in the shower. The bathroom was clean and they provided facecloths as well as towels. There was a sink in the bathroom as well as one outside the bathroom door. Room had a balcony. I would definitely stay hear again for the combination location, affordability, cleanliness and friendliness of staff."

Frequently asked questions

What are some accommodations with pools in Bailey Island?

Quality Inn & Suites South Portland: Hotel located near State Theatre. Provides free self parking, a pool, and complimentary wireless internet access. Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel: Hotel located near Maine Mall. Features an indoor pool, an outdoor pool, and daily. Clarion Hotel Portland Airport ME: Features a seasonal outdoor pool, an indoor pool, and a sauna. Clarion Pointe South Portland: Hotel, 4-minute walk from Cross Insurance Arena. Provides a sauna, a pool, and complimentary bicycles. Portland Harbor Hotel: Hotel located near State Theatre. Features buffet, a seasonal outdoor pool, and complimentary wireless internet access.

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

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

Our top choices for Bailey Island hotels with a pool