The Best Hotels with a Pool in Bailey Island, ME from ￥17,291 in 2026

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

Clarion Hotel Portland Airport ME : Hotel, 11-minute walk from Thompson's Point. Features free self parking, a pool, and complimentary wireless internet access. Portland Harbor Hotel : Hotel, 11-minute walk from Maine Medical Center. Offers daily, a seasonal outdoor pool, and complimentary wireless internet access. Cambria Hotel Portland Downtown-Old Port : Hotel, 1-minute walk from Maine Mall. Features a snack bar/deli, an outdoor pool, and free self parking. Portland Regency Hotel & Spa : Hotel, 6-minute walk from Maine Mall. Offers an indoor pool, an outdoor pool, and daily. La Quinta Inn & Suites by Wyndham Portland DT/Maine Med : Hotel, 5-minute walk from State Theatre. Offers a sauna, a pool, and complimentary bicycles.

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Our top choices for Bailey Island hotels with a pool

Bluebird Ocean Point Inn

Ocean Point

Seasonal oceanfront pool with coastal views and black sand beach access creates a perfect Maine summer escape.

￥39,457 total

includes taxes & fees

Jun 23 - Jun 24

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.

￥23,320 total

includes taxes & fees

Jun 28 - Jun 29

Best Western Plus Brunswick Bath

Brunswick

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

￥18,864 total

includes taxes & fees

Jun 28 - Jun 29

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.

￥22,335 total

includes taxes & fees

Jun 21 - Jun 22

Best Western Freeport Inn

Freeport

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

￥17,327 total

includes taxes & fees

Jun 16 - Jun 17

Smuggler's Cove Inn

East Boothbay

Pristine saltwater pool with bay views creates refreshing coastal sanctuary at beachside hotel.

￥44,518 total

includes taxes & fees

Jun 29 - Jun 30

Clarion Pointe South Portland

Thorton Heights

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

￥17,291 total

includes taxes & fees

Jul 1 - Jul 2

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

Ocean Gate Inn

Southport

Seasonal outdoor pool with sun loungers and umbrellas offers serene bay views at this Maine retreat.

￥39,584 total

includes taxes & fees

Jun 24 - Jun 25

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

Breakfast included

4 stars

Top Bailey Island Hotel Reviews

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent

"We only stayed for one night but they were quick and efficient and the bedroom was nicely kept and clean!"

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"The check-in was so easy and the staff was so friendly and helpful. They gave us recommendations for food and sights. The location was perfect for both the old port and the art district. The room was beautiful and welcoming but was even better was the beautiful view of the bay. We loved waking up to the beautiful view. Parking was easy and the hotel was comfortable."

DoubleTree by Hilton Hotel Portland

8/10 Good

"Great location. Nice room clean and tidy. Hotel breakfast on sunday was excellent. Parking close. Big indoor pool. As always on weekends in these areas tons of kids travel sports people. Dont like that at all. Noisy, crowded lobby and kids running . Easy access to Portland! Nice weekend"

Frequently asked questions

What are some accommodations with pools in Bailey Island?

Clarion Hotel Portland Airport ME: Hotel, 11-minute walk from Thompson's Point. Features free self parking, a pool, and complimentary wireless internet access. Portland Harbor Hotel: Hotel, 11-minute walk from Maine Medical Center. Offers daily, a seasonal outdoor pool, and complimentary wireless internet access. Cambria Hotel Portland Downtown-Old Port: Hotel, 1-minute walk from Maine Mall. Features a snack bar/deli, an outdoor pool, and free self parking. Portland Regency Hotel & Spa: Hotel, 6-minute walk from Maine Mall. Offers an indoor pool, an outdoor pool, and daily. La Quinta Inn & Suites by Wyndham Portland DT/Maine Med: Hotel, 5-minute walk from State Theatre. Offers a sauna, a pool, and complimentary bicycles.

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, Cobwork Bridge, and Mackerel Cove 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.

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