The Best Hotels with a Pool in Bailey Island, ME from NT$2,668 in 2026

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

The Westin Portland Harborview : Hotel located near Thompson's Point. Features a sauna, a pool, and complimentary bicycles. Cambria Hotel Portland Downtown-Old Port : Hotel located near Thompson's Point. Offers a snack bar/deli, an indoor pool, and buffet. Portland Harbor Hotel : Hotel located near Thompson's Point. Features a snack bar/deli, an indoor pool, and buffet. Holiday Inn Portland-By the Bay by IHG : Hotel located near Thompson's Point. Offers daily, a seasonal outdoor pool, and complimentary wireless internet access. Portland Regency Hotel & Spa : Hotel located near Thompson's Point. Provides complimentary wired internet access, an indoor pool, and LCD televisions.

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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.

NT$7,034 total

includes taxes & fees

May 13 - May 14

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$2,104 total

includes taxes & fees

Apr 26 - Apr 27

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

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

NT$4,300 total

includes taxes & fees

Apr 27 - Apr 28

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.

NT$3,953 total

includes taxes & fees

May 7 - May 8

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$2,668 total

includes taxes & fees

Apr 16 - Apr 17

The Harraseeket Inn & Event House Freeport Downtown

Freeport

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

NT$4,125 total

includes taxes & fees

Apr 30 - May 1

Hampton Inn Bath (Brunswick Area)

Bath

Splash into year-round aquatic bliss at this welcoming hotel with a refreshing indoor pool and scenic waterfront location.

NT$5,244 total

includes taxes & fees

May 10 - May 11

Inn By The Sea

Cape Elizabeth

Oceanside luxury with a full-service spa and serene outdoor pool awaits at this coastal retreat.

NT$8,363 total

includes taxes & fees

Apr 15 - Apr 16

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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

10/10 Excellent

"Front desk people were super kind, the hotel is very close to all the stores and places to eat!"

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"We only stayed for a night but we had a wonderful stay at this hotel, and what truly made the experience stand out was the exceptional staff, Richard. When we asked him for a lunch recommendation, he suggested a fantastic local spot! His knowledge of the area and willingness to go the extra mile made us feel well taken care of throughout our stay. It’s rare to find such a perfect blend of professionalism and friendliness. I would absolutely return and highly recommend this hotel to anyone looking for not just comfort, but outstanding service as well."

Frequently asked questions

What are some accommodations with pools in Bailey Island?

The Westin Portland Harborview: Hotel located near Thompson's Point. Features a sauna, a pool, and complimentary bicycles. Cambria Hotel Portland Downtown-Old Port: Hotel located near Thompson's Point. Offers a snack bar/deli, an indoor pool, and buffet. Portland Harbor Hotel: Hotel located near Thompson's Point. Features a snack bar/deli, an indoor pool, and buffet. Holiday Inn Portland-By the Bay by IHG: Hotel located near Thompson's Point. Offers daily, a seasonal outdoor pool, and complimentary wireless internet access. Portland Regency Hotel & Spa: Hotel located near Thompson's Point. Provides 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, 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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