Title: Book the Best Hotels with POOL in Bailey Island in 2026 | 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 showing general coastal views](https://images.trvl-media.com/place/6046825/3641ac6e-a5fc-4f22-a47d-0c23ea40681b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046825/3641ac6e-a5fc-4f22-a47d-0c23ea40681b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-26&endDate=2026-01-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-27&endDate=2026-01-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/a014d527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/bdc4333d.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 [](https://www.expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information) Thorton Heights 7.6/10 Good (411 reviews) "Under renovations but still a good stay. Pool was very well kept and heated. Staff were very accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $99 CA $108 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/01a4aa17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/0e129270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/84e040b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/1000000/20000/18700/18662/f72fdddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Portland Airport Maine Mall [](https://www.expedia.ca/South-Portland-Hotels-Spark-By-Hilton-Portland-Airport-Maine-Mall.h18662.Hotel-Information) South Portland 7.8/10 Good (1,385 reviews) "No frills, but great location and price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $101 CA $111 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/South-Portland-Hotels-Spark-By-Hilton-Portland-Airport-Maine-Mall.h18662.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/627581df.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) ![In-room safe, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/3701f117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/19000000/18960000/18952900/18952854/c3cda57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Portland Airport Area [](https://www.expedia.ca/Portland-Hotels-Tru-By-Hilton-Portland-Airport-Area.h18952854.Hotel-Information) South Portland 8.8/10 Excellent (1,720 reviews) "The perfect hotel if you’re looking for a cozy place for a quick stopover. The staff was very friendly and welcoming. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $91 CA $100 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Portland-Hotels-Tru-By-Hilton-Portland-Airport-Area.h18952854.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/4f4bd485.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/0cb4ca97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/f3b41288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Long Creek Hotel by IHG [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Airport.h24280.Hotel-Information) South Portland 7.4/10 Good (1,011 reviews) "Enjoyed the stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Farouq CA $99 CA $108 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Airport.h24280.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/965f6d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/73a05b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/b990d573.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) ### The Harraseeket Inn & Event House Freeport Downtown [](https://www.expedia.ca/Portland-Hotels-Harraseeket-Inn.h51266260.Hotel-Information) Freeport 9.4/10 Exceptional (888 reviews) "Good place and good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill CA $156 CA $170 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Portland-Hotels-Harraseeket-Inn.h51266260.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/17e160ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/26dc82a5.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) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/87d2a7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Portland [](https://www.expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) South Portland 8.0/10 Very good (1,336 reviews) "We had a great stay! Friendly, comfortable and clean. Great location too. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Jo CA $102 CA $111 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1e92d45b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Accessible, Non Smoking | Living area](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/ce637b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/d5d40c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/c7f9c4d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Portland Downtown - Waterfront [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) Downtown Portland 8.8/10 Excellent (1,025 reviews) "The hotel was lovely, very clean and warm. The staff was extremely friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $122 CA $135 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/e40c347e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/4f5c0299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/cbc24127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LED TV with cable channels, TV, MP3 dock](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/c8e21f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Portland Maine [](https://www.expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information) Portland 9.4/10 Exceptional (1,155 reviews) "Great spot next to the airports " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $142 CA $157 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.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) ![Lounge](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/415bf320.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) ![37-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/w3837h2557x3y3-d064711d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Portland Downtown Waterfront [](https://www.expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) Downtown Portland 9.2/10 Wonderful (1,007 reviews) "So good we extended our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $141 CA $156 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/a14b3a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/a3d98684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/efcbbed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2803900/2803802/5ba6b9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn Portland Downtown/Waterfront [](https://www.expedia.ca/Portland-Hotels-Residence-Inn-By-Marriott-Portland-Downtown-Waterfront.h2803802.Hotel-Information) East Bayside 8.8/10 Excellent (1,000 reviews) "Great parking, friendly staff, good healthy breakfast options, good location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ben CA $130 CA $144 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Portland-Hotels-Residence-Inn-By-Marriott-Portland-Downtown-Waterfront.h2803802.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=2026-02-09&endDate=2026-02-10®ionId=6046825&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Bailey Island Hotel Reviews ![Hilton Garden Inn Portland Downtown Waterfront](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/0e1014a3_y.jpg) ### Hilton Garden Inn Portland Downtown Waterfront 10/10 Excellent "room was spotless and I like all of the toiletries in the bathroom, shampoo conditioner face soap etc, Loved the hotel and staff was super courteous and helpful Thank You" [](https://expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) ![Embassy Suites by Hilton Portland Maine](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/cbc24127_y.jpg) ### Embassy Suites by Hilton Portland Maine 10/10 Excellent "Staff was excellent, amenities were spectacular. Overall the best stay in years!" [](https://expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information) ![Holiday Inn Portland-By the Bay by IHG](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/e922ee9f_y.jpg) ### Holiday Inn Portland-By the Bay by IHG 10/10 Excellent "Yes" [](https://expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) ![Hyatt Place Portland Downtown - Old Port Square](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/b4e33349_y.jpg) ### Hyatt Place Portland Downtown - Old Port Square 10/10 Excellent "great people" [](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg) ### Hampton Inn Portland Downtown - Waterfront 10/10 Excellent "Needs more options for breakfast " [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg) ### Portland Regency Hotel & Spa 10/10 Excellent "Everything was great…the staff was very friendly." [](https://expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![Long Creek Hotel by IHG](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/f3b41288_y.jpg) ### Long Creek Hotel by IHG 10/10 Excellent "Everything was fine here. Took forever to find someone who worked there in the morning but when we did she was able to help me." [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Airport.h24280.Hotel-Information) ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg) ### Clarion Hotel Portland Airport ME 10/10 Excellent "Very helpful and very clean room" [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information) ![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/33bb60f2_y.jpg) ### DoubleTree by Hilton Hotel Portland 10/10 Excellent "Nice clean room." [](https://expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Bailey Island? ### What is there to see and do in Bailey Island? ### When is the best time to book a hotel with a pool in Bailey Island? ## 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) - 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