The Best Hotels with a Pool in Bailey Island, ME from NT$1,916 in 2026

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

Portland Harbor Hotel : Hotel located near Thompson's Point. Features a sauna, a pool, and complimentary bicycles. Portland Regency Hotel & Spa : Hotel located near Thompson's Point. Features daily, a seasonal outdoor pool, and complimentary wireless internet access. Cambria Hotel Portland Downtown-Old Port : Hotel, 11-minute walk from Thompson's Point. Offers free self parking, a pool, and complimentary wireless internet access. HomeAwhile : Hotel located near Thompson's Point. Offers a snack bar/deli, an indoor pool, and buffet. Inn at St John Portland In-Town : Hotel located near Thompson's Point. Features an indoor pool, an outdoor pool, and daily.

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Our top choices for Bailey Island hotels with a pool

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.

NT$1,916 total

includes taxes & fees

Jun 1 - Jun 2

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.

NT$4,210 total

includes taxes & fees

May 31 - Jun 1

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.

NT$3,114 total

includes taxes & fees

Jun 7 - Jun 8

Bluebird Ocean Point Inn

Ocean Point

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

NT$7,123 total

includes taxes & fees

Jun 8 - Jun 9

Best Western Plus Brunswick Bath

Brunswick

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

NT$3,446 total

includes taxes & fees

Jun 10 - Jun 11

The Harraseeket Inn & Event House Freeport Downtown

Freeport

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

NT$4,408 total

includes taxes & fees

May 31 - Jun 1

Newagen Seaside Inn

Southport

Discover seaside tranquility at this coastal retreat with a refreshing outdoor pool and tennis courts for active summer days.

NT$6,784 total

includes taxes & fees

May 31 - Jun 1

Standard Room, 2 Queen Beds, Balcony, Pool View (Anchor Building) | Balcony

Smuggler's Cove Inn

East Boothbay

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

NT$6,518 total

includes taxes & fees

Jun 1 - Jun 2

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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

Portland Regency Hotel & Spa

10/10 Excellent

"Portland Regency Inn and Spa is an amazing place to stay. It is centrally located in the Old Port area of Portland. The staff and amenities were incredible. Next time we visit Portland we will definitely stay again."

Embassy Suites by Hilton Portland Maine

6/10 Okay

"Housekeeping was not great. I had to ask if our room would be cleaned as it was past 6pm and was not cleaned. I found out they only clean every three days. This was Sunday. Room serviced Monday but not cleaned until Friday when I asked. There was sticky stuff on the floors and beds were never made. The free breakfast was not very good although the omelet station was good. The location is great for first timers visiting Maine."

Frequently asked questions

What are some accommodations with pools in Bailey Island?

Portland Harbor Hotel: Hotel located near Thompson's Point. Features a sauna, a pool, and complimentary bicycles. Portland Regency Hotel & Spa: Hotel located near Thompson's Point. Features daily, a seasonal outdoor pool, and complimentary wireless internet access. Cambria Hotel Portland Downtown-Old Port: Hotel, 11-minute walk from Thompson's Point. Offers free self parking, a pool, and complimentary wireless internet access. HomeAwhile: Hotel located near Thompson's Point. Offers a snack bar/deli, an indoor pool, and buffet. Inn at St John Portland In-Town: Hotel located near Thompson's Point. Features an indoor pool, an outdoor pool, and daily.

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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