The Best Hotels with a Pool in Bailey Island, ME from AED 621 in 2026

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

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med : Hotel, 11-minute walk from Maine Medical Center. Features daily, a seasonal outdoor pool, and complimentary wireless internet access. Portland Harbor Hotel : Hotel located near Maine Mall. Features an indoor pool, an outdoor pool, and daily. Cambria Hotel Portland Downtown-Old Port : Hotel, 4-minute walk from Cross Insurance Arena. Provides a sauna, a pool, and complimentary bicycles. Clarion Pointe South Portland : Hotel steps from Casco Bay Lines Ferry Terminal. Offers a snack bar/deli, an indoor pool, and buffet. Comfort Inn South Portland Airport : Hotel, 11-minute walk from Thompson's Point. Provides free self parking, a pool, and complimentary wireless internet access.

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Our top choices for Bailey Island hotels with a pool

Smuggler's Cove Inn

East Boothbay

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

AED 1,010 total

includes taxes & fees

12 Jul - 13 Jul

Bluebird Ocean Point Inn

Ocean Point

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

AED 886 total

includes taxes & fees

29 Jul - 30 Jul

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

Linekin Bay Resort

Boothbay Harbor

Seasonal poolside paradise with waterfront views and tennis courts awaits.

AED 1,255 total

includes taxes & fees

9 Jul - 10 Jul

Woodlandview Lodge | 2 Queens + Porch

Boothbay Harbor

AED 2,719 total

includes taxes & fees

15 Jul - 16 Jul

Holland Room 2 | Lighthouse View + Ocean Deck

Boothbay Harbor

AED 2,307 total

includes taxes & fees

12 Jul - 13 Jul

Little Spruce Cottage | Wood Stove + Porch

Boothbay Harbor

AED 3,796 total

includes taxes & fees

11 Jul - 12 Jul

Spruce Point Inn

Boothbay Harbor

Splash into paradise with a waterside retreat that promises poolside relaxation and bay views to soothe your soul.

AED 2,095 total

includes taxes & fees

12 Jul - 13 Jul

Harbour Towne Inn on the Waterfront

Boothbay Harbor

Harborside inn offers a refreshing outdoor pool experience steps from coastal adventures.

AED 1,129 total

includes taxes & fees

9 Jul - 10 Jul

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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

"Nice clean room and a helpful staff. Enjoyable stay."

Embassy Suites by Hilton Portland Maine

10/10 Excellent

"The hotel’s location is excellent, especially for travelers arriving on late-night flights. It is within walking distance of the airport, making it very convenient to reach without needing a shuttle or taxi. Another big advantage is that the hotel is also just a short walk from the rental car center, making it easy to pick up a rental car the next morning and continue your trip. The room was clean and comfortable, and the staff were friendly and welcoming. Overall, it was a very convenient and pleasant stay, and I would definitely recommend this hotel to anyone flying into or out of Portland."

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Frequently asked questions

What are some accommodations with pools in Bailey Island?

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med: Hotel, 11-minute walk from Maine Medical Center. Features daily, a seasonal outdoor pool, and complimentary wireless internet access. Portland Harbor Hotel: Hotel located near Maine Mall. Features an indoor pool, an outdoor pool, and daily. Cambria Hotel Portland Downtown-Old Port: Hotel, 4-minute walk from Cross Insurance Arena. Provides a sauna, a pool, and complimentary bicycles. Clarion Pointe South Portland: Hotel steps from Casco Bay Lines Ferry Terminal. Offers a snack bar/deli, an indoor pool, and buffet. Comfort Inn South Portland Airport: Hotel, 11-minute walk from Thompson's Point. Provides free self parking, a 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, 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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