Title: Book the Best Hotels with POOL in Bailey Island in 2025 | Expedia.ca [Bailey Island Travel Guide](https://expedia.ca/Bailey-Island.dx6046825)[Hotels in Bailey Island](https://expedia.ca/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Vacation Rentals in Bailey Island](https://expedia.ca/Bailey-Island-Vacation-Rentals.d6046825.Travel-Guide-VacationRentals)[Bailey Island Car Rentals](https://expedia.ca/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide)[Bailey Island Vacation Packages](https://expedia.ca/Bailey-Island.d6046825.Destination-Travel-Guides) ![Bailey Island which includes general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265181-Central-Coast-Maine.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Bailey Island, ME from CA $109 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Bailey Island Hotels with a Pool Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2025-10-13&endDate=2025-10-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2025-10-14&endDate=2025-10-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Bailey Island Hotels with a Pool ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/2233a3c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Television](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/e64c361a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/433cc32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/bcaa0376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Germaine Inn South Portland South Portland 7.6/10 Good (316) "Very nice remake of an old Howard Johnson, conveniently located for road trip" CA $126 CA $137 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/7d36c6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/6ffb8399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/27ffce50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Portland Airport Maine Mall South Portland 7.8/10 Good (1344) "Great parking and quite area." CA $114 CA $124 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/South-Portland-Hotels-Spark-By-Hilton-Portland-Airport-Maine-Mall.h18662.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/c3cda57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/03c54bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/627581df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/7762fb2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Portland Airport Area South Portland 9.0/10 Wonderful (1573) "Third stay here and as always, its just perfect " CA $114 CA $124 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Tru-By-Hilton-Portland-Airport-Area.h18952854.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/e5da0114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/d379976a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/9d8f8d9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/0873dd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Independents Long Creek Hotel by IHG South Portland 7.4/10 Good (1012) "Look good , very friendly staff " CA $100 CA $109 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Airport.h24280.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/3516b137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/2e48d234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/513ce4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/0e1014a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Portland Downtown Waterfront Downtown Portland 9.2/10 Wonderful (1015) "Great location, easy valley parking, clean rooms, friendly staff" CA $154 CA $170 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/51604711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; garden views](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/24ae4e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/6905e33d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/d7b085e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harraseeket Inn & Event House Freeport Downtown Freeport 9.4/10 Exceptional (823) "Within walking distance of many restaurants and L L Bean….a really nice place to stay" CA $167 CA $182 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Harraseeket-Inn.h51266260.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/290000/282000/281934/63de006c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/282000/281934/145cd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/290000/282000/281934/3f09a2e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/282000/281934/65d64cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Freeport/Brunswick Freeport 9.0/10 Wonderful (1004) "Hotel was great, super friendly and helpful staff, breakfast had many choices, very clean. " CA $131 CA $143 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-FreeportBrunswick.h281934.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/39000000/38230000/38230000/38229978/bf446f6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible | Living area](https://images.trvl-media.com/lodging/39000000/38230000/38230000/38229978/93e2d435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38230000/38230000/38229978/1fa2f918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38230000/38230000/38229978/b5947c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Portland West Nasons Corner 8.8/10 Excellent (573) "Parking was great , shopping & restaurants nearby, great breakfast, clean comfortable rooms & friendly helpful staff." CA $123 CA $136 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-Suites-Portland-West.h38229978.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695918/2b9919b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695918/ba1ba6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695918/e8fe9006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1700000/1696000/1695918/fa5edabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Portland Airport South Portland 9.0/10 Wonderful (1006) "Very close to airport. " CA $123 CA $134 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Courtyard-By-Marriott-Portland-Airport.h1695918.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/33bb60f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/385a7714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/6983fdb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/41cba30c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Portland South Portland 8.0/10 Very good (1271) "Friendly staff and clean hotel to go t near shopping and restaurants. " CA $114 CA $124 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=6046825&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Bailey Island Hotel Reviews ![Hampton Inn Portland Downtown - Waterfront](//images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg) ### Hampton Inn Portland Downtown - Waterfront 10/10 Excellent "The Hampton Inn Portland Downtown Waterfront is in an excellent location near Old Port and the waterfront restaurants. It was very easy to retreat to our room during the day to cool down and relax in between sightseeing and shopping. The parking is weirdly expensive for such a hotel, but the valets were professional and easy to work with." [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) ![Fireside Inn & Suites Portland](//images.trvl-media.com/lodging/1000000/10000/9900/9842/bc09b846_y.jpg) ### Fireside Inn & Suites Portland 10/10 Excellent "clean room. staff very helpful" [](https://expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information) ![Portland Regency Hotel & Spa](//images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg) ### Portland Regency Hotel & Spa 10/10 Excellent "We loved our stay at Portland Regency! Staff were friendly, welcoming and helpful and responded immediately to any requests. We did not dine at the hotel but enjoy the basement bar. The room, whilst lacking a 'view' was large and the bed was enormous. The bathroom had everything we could ask for and more! We loved being so central that we could nip back several times a day in the unseasonable heat to refresh ourselves with the air con!" [](https://expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Portland DT/Maine Med](//images.trvl-media.com/lodging/1000000/30000/23500/23500/8325dcb5_y.jpg) ### La Quinta Inn & Suites by Wyndham Portland DT/Maine Med 10/10 Excellent "The room was clean and nice. They provided a wonderful breakfast. With eggs, sausage, bread & waffles." [](https://expedia.ca/Portland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Portland.h23500.Hotel-Information) ![Clarion Hotel Portland](//images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg) ### Clarion Hotel Portland 10/10 Excellent "We enjoyed this place very much. Highly recommend it to everyone. " [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information) ![Ramada Plaza by Wyndham Portland](//images.trvl-media.com/lodging/1000000/10000/3000/2908/f5509e04_y.jpg) ### Ramada Plaza by Wyndham Portland 10/10 Excellent "The establishment was clean and everything went well" [](https://expedia.ca/Portland-Hotels-Ramada-Plaza-By-Wyndham-Portland.h2908.Hotel-Information) ![Hyatt Place Portland Downtown - Old Port Square](//images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/b4e33349_y.jpg) ### Hyatt Place Portland Downtown - Old Port Square 10/10 Excellent "Staff friendly and willing to help. " [](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Holiday Inn Portland-By the Bay by IHG](//images.trvl-media.com/lodging/1000000/20000/12000/11991/e922ee9f_y.jpg) ### Holiday Inn Portland-By the Bay by IHG 10/10 Excellent "Clean room. " [](https://expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) ![Germaine Inn South Portland](//images.trvl-media.com/lodging/1000000/30000/23800/23779/b95e6193_y.jpg) ### Germaine Inn South Portland 10/10 Excellent "Bathtub had some hairs, but other than that, the rest of the room was clean" [](https://expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Bailey Island? > [Clarion Hotel Portland](https://www.expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information): Hotel, 11-minute walk from Thompson's Point. Features free self parking, a pool, and complimentary wireless internet access. [Germaine Inn South Portland](https://www.expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information): Hotel located near Maine Mall. Offers an indoor pool, an outdoor pool, and daily. [Fireside Inn & Suites Portland](https://www.expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information): Hotel located near Thompson's Point. Provides a seasonal outdoor pool, an indoor pool, and a sauna. [Portland Harbor Hotel](https://www.expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information): Hotel located near Thompson's Point. Offers daily, a seasonal outdoor pool, and complimentary wireless internet access. [Comfort Inn Airport](https://www.expedia.ca/Portland-Hotels-Comfort-Inn-Airport.h27041.Hotel-Information): Hotel located near Thompson's Point. Provides a snack bar/deli, an indoor pool, and buffet. ### What is there to see and do in Bailey Island? > Make a point to visit attractions like Ragged Island and 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Business Hotels in Bangor](https://www.expedia.ca/Bangor-Hotels-Business-Hotel.0-0-d6050918-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Bangor](https://www.expedia.ca/Bangor-Hotels-LGBT-Friendly-Hotel.0-0-d6050918-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Condo Rentals in Bustins Island](https://www.expedia.ca/Bustins-Island-Condos.d553248635976478507-aaCondos.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Cape Elizabeth](https://www.expedia.ca/Cape-Elizabeth-Hotels-Beach-Hotel.0-0-d55620-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Cape Elizabeth](https://www.expedia.ca/Cape-Elizabeth-Hotels-Boutique-Hotel.0-0-d55620-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cape Elizabeth](https://www.expedia.ca/Cape-Elizabeth-Hotels-Cheap-Hotels.0-0-d55620-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Beach Hotel Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-Beach-Hotel.0-0-d6046209-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Long Island](https://www.expedia.ca/Long-Island-Hotels-Hotel-With-Pool.0-0-d6046209-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Long Island](https://www.expedia.ca/Long-Island-Hotels-Hotels-With-Balconies.0-0-d6046209-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-LGBT-Friendly-Hotel.0-0-d6046209-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-Luxury-Hotel.0-0-d6046209-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Long Island](https://www.expedia.ca/Long-Island-Hotels-Romantic-Hotel.0-0-d6046209-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Monhegan Island](https://www.expedia.ca/Monhegan-Island-Hotels-Beach-Hotel.0-0-d183284-tBeachHotel.Travel-Guide-Filter-Hotels) - 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[Kk Leisure Rental Cars in Casco Bay Islands](https://www.expedia.ca/KK-Leisure-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1133.Car-Rental-Guide-Suppliers) - [National Car Rental Rental Cars in Great Island](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Great-Island.d553248635976193455-c42.Car-Rental-Guide-Suppliers) - [Thai Cars Rental Cars in Casco Bay Islands](https://www.expedia.ca/Thai-Cars-Car-Rentals-In-Casco-Bay-Islands.d553248621532668098-c1027.Car-Rental-Guide-Suppliers) - [Great Island Vacation Rentals](https://www.expedia.ca/Great-Island-Vacation-Rentals.d553248635976193455.Travel-Guide-VacationRentals) - [Book Hotels with a Pool in Bailey Island on Expedia.com](https://www.expedia.com/Bailey-Island-Hotels-Hotel-With-Pool.0-0-d6046825-tHotelwithPool.Travel-Guide-Filter-Hotels)