Title: Bailey Island B&B: Find the Best Bed and Breakfast from CA $120 | 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 featuring rugged coastline and a house](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Bailey Island from CA $120 - ![](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 prices for these dates Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6046825&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Bailey Island bed & breakfast ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/70000/67500/67481/c8f4e76e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/70000/67500/67481/bebb6386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/1000000/70000/67500/67481/3ca9202d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/70000/67500/67481/4319ee50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at St John Portland In-Town [](https://www.expedia.ca/Portland-Hotels-Inn-At-St-John-Portland-In-Town.h67481.Hotel-Information) Valley Street 8.8/10 Excellent (1135) "Friendly helpful staff and a nice independent location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $110 CA $120 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Portland-Hotels-Inn-At-St-John-Portland-In-Town.h67481.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/2f62fb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pemaquid Point Room](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/7c9e969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/46b14734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/ce6ea468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brewster House Bed & Breakfast [](https://www.expedia.ca/Portland-Hotels-Brewster-House-Bed-Breakfast.h126758.Hotel-Information) Freeport 9.8/10 Exceptional (114) "The food was wonderful and the hospitality was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia CA $230 CA $251 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Portland-Hotels-Brewster-House-Bed-Breakfast.h126758.Hotel-Information) ![Deluxe Room, 1 King Bed, Harbour View, Oceanfront | Water view](https://images.trvl-media.com/lodging/9000000/8320000/8318100/8318038/0365c6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Harbour View, Oceanfront](https://images.trvl-media.com/lodging/9000000/8320000/8318100/8318038/6a8689f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Private Bathroom | Living area](https://images.trvl-media.com/lodging/9000000/8320000/8318100/8318038/a7378ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/9000000/8320000/8318100/8318038/05544c82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harborage Inn on the Oceanfront [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Harborage-Inn-On-The-Oceanfront.h8318038.Hotel-Information) Boothbay Harbor 9.6/10 Exceptional (223) "Yes, the room was spotless and comfortable. Check in was easy. Breakfast was delicious and appeared right on time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie CA $292 CA $318 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Harborage-Inn-On-The-Oceanfront.h8318038.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1512100/1512059/dd96af6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1520000/1512100/1512059/5ea6d96f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1512100/1512059/10d66cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1520000/1512100/1512059/bce07578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kendall Inn [](https://www.expedia.ca/Portland-Hotels-Kendall-Tavern-Inn.h1512059.Hotel-Information) Freeport 9.8/10 Exceptional (145) "Quaint stay. Enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $231 CA $252 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Portland-Hotels-Kendall-Tavern-Inn.h1512059.Hotel-Information) ![Baxter](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/4e66cf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/60dba00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/bc3317cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Billiards](https://images.trvl-media.com/lodging/1000000/210000/200300/200246/20c86715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blind Tiger Portland - Danforth Street. [](https://www.expedia.ca/Portland-Hotels-Blind-Tiger-Guest-House.h200246.Hotel-Information) West End 9.6/10 Exceptional (167) "The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darby CA $284 CA $310 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Portland-Hotels-Blind-Tiger-Guest-House.h200246.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/12000000/11490000/11484600/11484573/db56ab15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/12000000/11490000/11484600/11484573/c6afbb33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Evergreen Room](https://images.trvl-media.com/lodging/12000000/11490000/11484600/11484573/b21b3f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11490000/11484600/11484573/7d9cb820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlebay Inn [](https://www.expedia.ca/Portland-Hotels-Candlebay-Inn.h11484573.Hotel-Information) Freeport 9.6/10 Exceptional (460) "The Candlebay Inn was a great stay! Staff was wonderful and the place was super cute and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paige CA $213 CA $232 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Portland-Hotels-Candlebay-Inn.h11484573.Hotel-Information) ![Stovall | Living area](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/ed6b0e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/8a9890d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/545bc193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12750000/12743300/12743204/926be017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blind Tiger Portland – Carleton Street [](https://www.expedia.ca/Portland-Hotels-Inn-On-Carleton.h12743204.Hotel-Information) West End 9.6/10 Exceptional (120) "Loved the place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $255 CA $278 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Portland-Hotels-Inn-On-Carleton.h12743204.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 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Harbour-Towne-Inn-On-The-Waterfront.h1209081.Hotel-Information) Boothbay Harbor 9.6/10 Exceptional (78) "Very nice comfortable room with friendly staff and excellent breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $366 CA $399 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Harbour-Towne-Inn-On-The-Waterfront.h1209081.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/26000000/25010000/25005400/25005328/e3f8dcf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/26000000/25010000/25005400/25005328/ef9e2994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/26000000/25010000/25005400/25005328/a98cd959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Edith Ann Room, 1 Queen bed, Shared bathroom. Credit cards accepted, Cash or Checks preferred](https://images.trvl-media.com/lodging/26000000/25010000/25005400/25005328/718f3676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fleetwood House Bed & Breakfast [](https://www.expedia.ca/Portland-Hotels-Fleetwood-House-Bed-Breakfast.h25005328.Hotel-Information) Rosemont 9.0/10 Wonderful (132) "Lovely, comfortable stay! So welcoming and accommodating. We only stayed one night but will keep this in mind next time we are in the area :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sadie CA $316 CA $345 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Portland-Hotels-Fleetwood-House-Bed-Breakfast.h25005328.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/5d783f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 Bedroom, Bathtub](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/20306c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/c17fb587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/e5c17fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The James Place Inn B&B [](https://www.expedia.ca/Portland-Hotels-The-James-Place-Inn-Bed-And-Breakfast.h1489274.Hotel-Information) Freeport 10/10 Exceptional (182) "Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $301 CA $329 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Portland-Hotels-The-James-Place-Inn-Bed-And-Breakfast.h1489274.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123480000/123476100/123476022/7dbac3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123480000/123476100/123476022/0344e907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123480000/123476100/123476022/58d1c64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/124000000/123480000/123476100/123476022/7e04fab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boothbay Harbor King Suite - Room 2 at Greenleaf Inn - Balcony, Harbor Views! [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Boothbay-Harbor-King-Suite-Room-2-At-Greenleaf-Inn-Balcony.h123476022.Hotel-Information) Boothbay Harbor CA $345 CA $421 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Boothbay-Harbor-King-Suite-Room-2-At-Greenleaf-Inn-Balcony.h123476022.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=2026-01-04&endDate=2026-01-05®ionId=6046825&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FBailey-Island-Bed-And-Breakfast.d6046825-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBailey-Island-Bed-And-Breakfast.d6046825-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Bailey Island Hotel Reviews ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg) ### Portland Harbor Hotel 10/10 Excellent "Room was spotless and the staff was so kind and welcoming " [](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.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 "From the front desk to the restaurant/bar and morning staff all were pleasant! Due to our breakfast staff, we changed our plans to eat dinner at the restaurant instead of eating at another establishment. We were not disappointed. Food and drinks were great! Our room was very clean. We will be staying at the Double Tree Hilton again. " [](https://expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.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 "Room was great, very clean. Staff were all very nice and even offered to blow up a beach ball for my daughter in the pool. " [](https://expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information) ![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 "This property was very clean and everyone was helpful and efficient. " [](https://expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg) ### The Westin Portland Harborview 10/10 Excellent "Helpful staff" [](https://expedia.ca/Portland-Hotels-The-Westin-Portland-Harborview.h6273.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 "Pleasant stay." [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.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 "It was a very pleasant experience we will definitely be staying here again. " [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Airport.h24280.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 "The hotel was quiet and our room had a great view of the harbor." [](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 corner" [](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ## Find out more about Bailey Island ## Bailey Island B&B information | Number of reviews | 2,729 | | ----------------- | ------- | | Accommodation | 29 B&B | | Lowest Price | CA $120 | | Highest Price | CA $421 | ## Frequently asked questions ### Searching for B&Bs in Bailey Island? ### Are you thinking about a B&B for your stay? ### What are the best bed and breakfasts in Bailey Island? ### What's the best time of year to stay at a B&B in Bailey Island? ### What is there to do in Bailey Island? ### How can I get to and around Bailey Island? ## Explore a world of travel with Expedia - 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