Title: Book the Best Hotels with POOL in Five Islands in 2025 | Expedia.ca [Hotels in Five Islands](https://expedia.ca/Five-Islands-Hotels.d553248635976385296.Travel-Guide-Hotels)[Vacation Rentals in Five Islands](https://expedia.ca/Five-Islands-Vacation-Rentals.d553248635976385296.Travel-Guide-VacationRentals)[Five Islands Car Rentals](https://expedia.ca/Car-Rentals-In-Five-Islands.d553248635976385296.Car-Rental-Guide)[Five Islands Vacation Packages](https://expedia.ca/Five-Islands.d553248635976385296.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Five Islands, ME from CA $166 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Five Islands Hotels with a Pool Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976385296&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976385296&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976385296&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976385296&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Five Islands Hotels with a Pool ![Oceanfront Deluxe King w/ porch | Beach/ocean view](https://images.trvl-media.com/lodging/25000000/24320000/24319800/24319759/3b52fec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sea Kist Oceanfront Cottage Suite | Living area](https://images.trvl-media.com/lodging/25000000/24320000/24319800/24319759/w5749h3976x0y0-af3434cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shore Oceanfront ADA King](https://images.trvl-media.com/lodging/25000000/24320000/24319800/24319759/5bcdf010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/25000000/24320000/24319800/24319759/0f9c8477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bluebird Ocean Point Inn Ocean Point 8.8/10 Excellent (539) "Staff was super friendly! Will stay again if in the area." CA $350 CA $404 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Ocean-Point-Inn.h24319759.Hotel-Information) ![Outdoor pool, open 7:30 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2130000/2130000/2129923/6496398a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2130000/2130000/2129923/ca7a6ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2130000/2130000/2129923/3eb1f126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Room, 2 Queen Beds, Balcony, Ocean View (Pier Building) | View from room](https://images.trvl-media.com/lodging/3000000/2130000/2130000/2129923/834b5f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Smuggler's Cove Inn East Boothbay 9.0/10 Wonderful (435) "Great views, family friendly, amazing breakfasts in a quiet part of Boothbay❤️" CA $245 CA $268 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Smugglers-Cove-Inn.h2129923.Hotel-Information) ![Daily buffet breakfast (USD 10 per person)](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/8ffdcddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Theatre show](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/8017bb8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/732283ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/6b31ff17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flagship Inn and Suites Boothbay Harbor 8.2/10 Very good (1007) "Good breakfast Convenient location " CA $147 CA $193 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Flagship-Inn-And-Suites.h894021.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/9000000/8090000/8082900/8082897/e842ee11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8090000/8082900/8082897/e54e92ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/9000000/8090000/8082900/8082897/2db2adee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8090000/8082900/8082897/f779e6ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newagen Seaside Inn Southport 9.4/10 Exceptional (337) "Location was beautiful and food was great. " CA $310 CA $376 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Newagen-Seaside-Inn.h8082897.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/35000000/34930000/34925200/34925132/61d970aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/35000000/34930000/34925200/34925132/da734f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/35000000/34930000/34925200/34925132/50243f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34930000/34925200/34925132/3039adca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cod Cove Inn, BW Signature Collection Edgecomb 9.0/10 Wonderful (457) "Lowkey and lovely inn very close to Booth bay, Newcastle and all the other towns we visited. We had a great stay!" CA $152 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Cod-Cove-Inn.h34925132.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/15000000/14660000/14657800/14657719/eec9d1a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/15000000/14660000/14657800/14657719/09c81ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 King Bed, Bay View | Balcony](https://images.trvl-media.com/lodging/15000000/14660000/14657800/14657719/47dcf3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/15000000/14660000/14657800/14657719/e94fc0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Linekin Bay Resort Boothbay Harbor 9.2/10 Wonderful (200) "Great place out of the way but also not far from town,loved it!" CA $378 CA $454 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Linekin-Bay-Resort.h14657719.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/893300/893209/7d3f5fe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893300/893209/86bcca46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/900000/893300/893209/a5acf401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/1000000/900000/893300/893209/76da18d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spruce Point Inn Boothbay Harbor 8.8/10 Excellent (388) "What a beautiful resort. I can’t wait to visit again. The staff were all wonderful well." CA $423 CA $531 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Spruce-Point-Inn.h893209.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1209100/1209081/c8b83a50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1210000/1209100/1209081/e2b9a938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1210000/1209100/1209081/a97dfc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1210000/1209100/1209081/de8a07d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour Towne Inn on the Waterfront Boothbay Harbor 9.6/10 Exceptional (74) "Liked decor, staff, and breakfast " CA $410 CA $447 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Harbour-Towne-Inn-On-The-Waterfront.h1209081.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/107000000/106100000/106093200/106093185/w1024h722x0y15-b9242c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106100000/106093200/106093185/w1024h679x0y44-512381a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106100000/106093200/106093185/e3f3ede7_edited_d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106100000/106093200/106093185/1c44e170_edited_b541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WoodlandView Ldg | Porch + Garden | No Hidden Fees Boothbay Harbor 10/10 Exceptional (1) "Hands down - best place to stay in Boothbay Harbor. It's quiet and quaint; right on the water. Love that they had free kayaks for guests to use. Wish we could've stayed longer! " CA $490 CA $610 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Woodlandview-Lodge-With-Porch-And-GardenFireplace.h106093185.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/103000000/102720000/102717400/102717353/f770d834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, internet](https://images.trvl-media.com/lodging/103000000/102720000/102717400/102717353/111aa980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102720000/102717400/102717353/7b2e850b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/103000000/102720000/102717400/102717353/37f32467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Superior Double Room - 2 Double Bed Boothway Harbor 6.0/10 (3) "Room smelled strongly of old cooked food (Indian?). Windows were already left open to air the room out when we arrived. Luckily, we arrived early enough to run the fan for a couple of hours prior to going to bed. Room should not have been rented that day. Am continental buffet was good. Coffee was pretty good." CA $180 CA $274 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Superior-Double-Room-2-Double-Bed.h102717353.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=2025-10-21&endDate=2025-10-22®ionId=553248635976385296&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Five Islands Hotel Reviews ![Fairfield Inn & Suites by Marriott Brunswick Freeport](//images.trvl-media.com/lodging/2000000/1090000/1086100/1086088/a735e9f6_y.jpg) ### Fairfield Inn & Suites by Marriott Brunswick Freeport 10/10 Excellent "Very comfortable beds and wonderful bedding. Rooms are a bit small. " [](https://expedia.ca/Boothbay-Harbor-Hotels-Fairfield-Inn-Suites-By-Marriott-Brunswick-Freeport.h1086088.Hotel-Information) ![Flagship Inn and Suites](//images.trvl-media.com/lodging/1000000/900000/894100/894021/8ffdcddf_y.jpg) ### Flagship Inn and Suites 10/10 Excellent "The rooms were very clean and cute. The staff and owner very friendly and helpful " [](https://expedia.ca/Boothbay-Harbor-Hotels-Flagship-Inn-And-Suites.h894021.Hotel-Information) ![Comfort Inn Brunswick](//images.trvl-media.com/lodging/1000000/10000/4100/4072/a1d01a3c_y.jpg) ### Comfort Inn Brunswick 10/10 Excellent "It is a beautiful property!" [](https://expedia.ca/Boothbay-Harbor-Hotels-Comfort-Inn-Brunswick-Freeport.h4072.Hotel-Information) ![Ocean Gate Resort](//images.trvl-media.com/lodging/1000000/900000/893200/893144/b444fb5c_y.jpg) ### Ocean Gate Resort 10/10 Excellent "Cool family friendly place with lots of activities (ping pong, minigolf, canoes and kayaks) and a beautiful location and view from all the rooms. Very generous and tasty breakfast, too." [](https://expedia.ca/Boothbay-Harbor-Hotels-Ocean-Gate-Resort.h893144.Hotel-Information) ![Relax Inn](//images.trvl-media.com/lodging/2000000/1370000/1368700/1368669/06364814_y.jpg) ### Relax Inn 10/10 Excellent "clean room" [](https://expedia.ca/Boothbay-Harbor-Hotels-Relax-Inn.h1368669.Hotel-Information) ![Residence Inn Bath Brunswick Area](//images.trvl-media.com/lodging/1000000/10000/2800/2756/123ef08d_y.jpg) ### Residence Inn Bath Brunswick Area 10/10 Excellent "VERY helpful front desk!!!! Great place to base out of for the area." [](https://expedia.ca/Boothbay-Harbor-Hotels-Residence-Inn-Bath-Brunswick-Area.h2756.Hotel-Information) ![Best Western Plus Brunswick Bath](//images.trvl-media.com/lodging/1000000/30000/27700/27652/dc0dd762_y.jpg) ### Best Western Plus Brunswick Bath 10/10 Excellent "Very nice staff" [](https://expedia.ca/Boothbay-Harbor-Hotels-Best-Western-Plus-Brunswick-Bath.h27652.Hotel-Information) ![Moonlight Inn](//images.trvl-media.com/lodging/1000000/10000/7300/7287/ff13265a_y.jpg) ### Moonlight Inn 10/10 Excellent "Thank you so much it is always great to stay here" [](https://expedia.ca/Boothbay-Harbor-Hotels-Moonlight-Inn.h7287.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Five Islands? > [Charming cottage near the beach with balcony, deck, grill, fireplace - dogs OK](https://www.expedia.ca/Georgetown-Hotels-Charming-Cottage-Retreat-With-Balcony-Bliss-And-Wi-Fi.h95789653.Hotel-Information): Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Travelers Inn](https://www.expedia.ca/Boothbay-Harbor-Hotels-Travelers-Inn.h8208979.Hotel-Information): Offers buffet, a seasonal outdoor pool, and flat-screen televisions. [Comfort Inn Brunswick](https://www.expedia.ca/Boothbay-Harbor-Hotels-Comfort-Inn-Brunswick-Freeport.h4072.Hotel-Information): Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Flagship Inn and Suites](https://www.expedia.ca/Boothbay-Harbor-Hotels-Flagship-Inn-And-Suites.h894021.Hotel-Information): Features a snack bar/deli, an indoor pool, and full. [The Federal](https://www.expedia.ca/Brunswick-Hotels-The-Federal.h75630171.Hotel-Information): Offers buffet, an indoor pool, and free self parking. ### What is there to see and do in Five Islands? > Make a point to visit attractions like Grimes Cove Beach and Coastal Maine Botanical Gardens. During your stay, check out sights such as Reid State Park, Burnt Island Living Lighthouse, and Boothbay Harbor Marina. ### When is the best time to book a hotel with a pool in Five Islands? > Taking into account the local weather in Five Islands is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Five Islands are January, March, December, and February, with each month seeing an average of 6 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [B&B in Arrowsic](https://www.expedia.ca/Arrowsic-Bed-And-Breakfast.d3000435431-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Arrowsic](https://www.expedia.ca/Arrowsic-Cabins.d3000435431-aaCabins.Travel-Guide-Accommodation) - [Townhomes in Arrowsic](https://www.expedia.ca/Arrowsic-Townhomes.d3000435431-aaTownhomes.Travel-Guide-Accommodation) - [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) - [Adults Only Resorts & in Boothbay Harbor](https://www.expedia.ca/Boothbay-Harbor-Hotels-Adults-Only-Resorts.0-0-d6057298-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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