The Best Hotels with a Pool in Bailey Island, ME from AED 281 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

Newagen Seaside Inn

Southport

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

Zachary

AED 587 total

includes taxes & fees

26 May - 27 May

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.

nial

AED 552 total

includes taxes & fees

26 May - 27 May

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.

Dorota

AED 320 total

includes taxes & fees

31 May - 1 Jun

Bluebird Ocean Point Inn

Ocean Point

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

Jeffrey

AED 767 total

includes taxes & fees

8 Jun - 9 Jun

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.

Peter

AED 281 total

includes taxes & fees

31 May - 1 Jun

Best Western Plus Brunswick Bath

Brunswick

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

Shana

AED 404 total

includes taxes & fees

3 Jun - 4 Jun

Captain's House 1BR Apt. Walk to everything.

Bath

Oceanside getaway with a shared community pool, private garden, and playground access just steps away from the beach.

Leslie F.

AED 460 total

includes taxes & fees

25 May - 26 May

The Harraseeket Inn & Event House Freeport Downtown

Freeport

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

Linda

AED 556 total

includes taxes & fees

25 May - 26 May

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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

Hyatt Place Portland Downtown - Old Port Square

8/10 Good

"Ideal location in the thick of Old Port. Walking distance to most of Portland Old Port main attractions. Staff are fantastic. They were very friendly and professional start to finish. Rooms were clean and comfortable."

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

10/10 Excellent

"Great hotel for a Seadogs game. The parking is safe and very accessible to the hotel rooms. The breakfast is great. The ice machine on floors 2 and 3 were not working but floors 1 and 4 were. Clean room with microwave and plenty of towels. Plenty of luggage trolleys. You can check in and out online. We booked again we liked it so much."

Portland Regency Hotel & Spa

6/10 Okay

"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix or Prime Video, and the girl at the front responded rather rudely that “we are a historic hotel, so we do not offer smart TVs.” We completely understand preserving the character of a historic property, but the response came across dismissive for what was just a simple question. We were also told that because parts of the hotel are older, some areas may not look as clean compared to newer hotels. While we appreciate the history and character of the property, cleanliness and customer service should still meet expectations regardless of the building’s age. We’ve enjoyed staying here in the past, which makes this visit more disappointing, and we hope these issues are addressed moving forward."

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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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