Title: Book the Best HISTORIC Hotels in Chebeague Island in 2026 | Expedia.ca [Hotels in Chebeague Island](https://expedia.ca/Chebeague-Island-Hotels.d6046986.Travel-Guide-Hotels)[Vacation Rentals in Chebeague Island](https://expedia.ca/Chebeague-Island-Vacation-Rentals.d6046986.Travel-Guide-VacationRentals)[Flights to Chebeague Island](https://expedia.ca/Cheap-Flights-To-Chebeague-Island.d6046986.Travel-Guide-Flights)[Chebeague Island Car Rentals](https://expedia.ca/Car-Rentals-In-Chebeague-Island.d6046986.Car-Rental-Guide)[Chebeague Island Vacation Packages](https://expedia.ca/Chebeague-Island.d6046986.Destination-Travel-Guides) ![Early morning harbor in Maine](https://images.trvl-media.com/place/6046986/e3672dae-ca9d-401e-a41d-f9e424fba1ca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046986/e3672dae-ca9d-401e-a41d-f9e424fba1ca.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 Chebeague Island Historic Hotels Tonight [Mar 16 - Mar 17](https://www.expedia.ca/Hotel-Search?regionId=6046986&startDate=2026-03-16&endDate=2026-03-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 17 - Mar 18](https://www.expedia.ca/Hotel-Search?regionId=6046986&startDate=2026-03-17&endDate=2026-03-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6046986&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6046986&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chebeague Island historic hotels ![Beach](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/456eee4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/031f8225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/5c9e0f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/92b9303c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### City Amenities, Casco Bay Sunrises and Natural Beauty [](https://www.expedia.ca/Portland-Hotels-City-Amenities.h34429189.Hotel-Information) East Deering 9.8/10 Exceptional (126 reviews) "Perfect location and the host was immediately repsonsive and always friendly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon L. CA $148 CA $356 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Portland-Hotels-City-Amenities.h34429189.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/18ed00db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/338ff9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/063e81f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32840000/32833100/32833020/108d7b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Lincoln beautiful home [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Little-Lincoln-Lovely-Home.h32833020.Hotel-Information) Brunswick 9.0/10 Wonderful (16 reviews) "The host was very welcoming and responsive when we had a question. We would stay here again when we come back to Brunswick. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. CA $108 CA $336 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-Little-Lincoln-Lovely-Home.h32833020.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/59add01a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/afb1af83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/46f0eb26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27540000/27534000/27533976/w2016h1286x0y0-21928c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2King Bed BR Private Apt Downtown Brunswick [](https://www.expedia.ca/Boothbay-Harbor-Hotels-2king-Bed-BR-Private-Apt-Downtown-Brunswick.h27533976.Hotel-Information) Brunswick 8.4/10 Very good (11 reviews) "Small place in a great location. Easily walk to several shops and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jillian B. CA $123 CA $321 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-2king-Bed-BR-Private-Apt-Downtown-Brunswick.h27533976.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/w1917h1645x3y0-c1000dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/8d027ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/w1920h1432x0y17-48abbb9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/1829e5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glorious getaway on Portland's Eastern Promenade. [](https://www.expedia.ca/Portland-Hotels-Glorious-Getaway-On-Portlands-Eastern-Promenade.h32668873.Hotel-Information) Munjoy Hill 9.8/10 Exceptional (172 reviews) "Very cute and comfy. We would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marie s. CA $200 CA $384 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Portland-Hotels-Glorious-Getaway-On-Portlands-Eastern-Promenade.h32668873.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/4847920a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/10493eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/17224a0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/d87ce049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centerview cottage [](https://www.expedia.ca/Harpswell-Hotels-Centerview-Cottage.h27476270.Hotel-Information) Harpswell 9.6/10 Exceptional (59 reviews) "Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin CA $405 CA $655 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Harpswell-Hotels-Centerview-Cottage.h27476270.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/917fa099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/46133e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/fa088373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Portland Regency Hotel & Spa [](https://www.expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) Downtown Portland 9.4/10 Exceptional (1,602 reviews) "Great value, I’d stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick CA $185 CA $205 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/5c42ecc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/824219c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, Netflix, streaming services](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/a3f31177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59960000/59959800/59959794/72cf4bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious and Contemporary Condo in the Heart of Portland - Close to Beach [](https://www.expedia.ca/Portland-Hotels-Spacious-And-Contemporary-Condo-In-The-Heart-Of-Portland-Close-To-Beach.h59959794.Hotel-Information) East Bayside 8.8/10 Excellent (37 reviews) "Overall a pleasing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mallory D. CA $182 CA $641 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Portland-Hotels-Spacious-And-Contemporary-Condo-In-The-Heart-Of-Portland-Close-To-Beach.h59959794.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/44b25a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/3f754004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/6ab78874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/10b6585a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound) [](https://www.expedia.ca/Brunswick-Hotels-Brand-New-Downtown-2BR-On-Noble-Next-To-Bowdoin.h59656609.Hotel-Information) Brunswick 9.6/10 Exceptional (30 reviews) "This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill C. CA $165 CA $459 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Brunswick-Hotels-Brand-New-Downtown-2BR-On-Noble-Next-To-Bowdoin.h59656609.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42070000/42069500/42069496/fade2032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/43000000/42070000/42069500/42069496/58339323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/43000000/42070000/42069500/42069496/c02e06e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/43000000/42070000/42069500/42069496/e678c4ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant condo - walk to Portland's best restaurants & Old Port [](https://www.expedia.ca/Portland-Hotels-Elegant-Condo-Walk-To-Portlands-Best-Restaurants-Old-Port.h42069496.Hotel-Information) East Bayside 9.2/10 Wonderful (77 reviews) "Property is clean quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Spencer S. CA $219 CA $691 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Portland-Hotels-Elegant-Condo-Walk-To-Portlands-Best-Restaurants-Old-Port.h42069496.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/w1917h1645x3y0-1a82cf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/fe48c018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/w1920h1432x0y17-47ca72aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/91a3f768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Portland getaway on the Eastern Promenade [](https://www.expedia.ca/Portland-Hotels-Adorable-Portland-Getaway-On-The-Eastern-Promenade.h32432059.Hotel-Information) Munjoy Hill 9.6/10 Exceptional (129 reviews) "Great location to explore Portland as many restaurants, breweries, and sites are within easy walking distance. Room is plants of space for 2 and the bed was comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rich M. CA $151 CA $280 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Portland-Hotels-Adorable-Portland-Getaway-On-The-Eastern-Promenade.h32432059.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=2026-03-30&endDate=2026-03-31®ionId=6046986&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chebeague Island Hotel Reviews ![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/17e160ed_y.jpg) ### DoubleTree by Hilton Hotel Portland 8/10 Good "Staff was excellent, room was clean and had good amenities. We had 1 broken elevator and the other to the west tower was very dirty. All in all i would stay again" [](https://expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) ![Hyatt Place Portland Downtown - Old Port Square](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/06fb9956_y.jpg) ### Hyatt Place Portland Downtown - Old Port Square 10/10 Excellent "In the perfect downtown location!" [](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc_y.jpg) ### Portland Regency Hotel & Spa 10/10 Excellent "The shuttle to the downtown area is a perk not advertised which is a great option " [](https://expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/1a7f326f_y.jpg) ### Portland Harbor Hotel 10/10 Excellent "Excelente " [](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) ![Inn at St John Portland In-Town](https://images.trvl-media.com/lodging/1000000/70000/67500/67481/c8f4e76e_y.jpg) ### Inn at St John Portland In-Town 10/10 Excellent "The only problem staying in that place is there’s no elevators. My room was on the third floor and I have really bad knees. I couldn’t leave my room for a couple days cause I couldn’t climb up those stairs.I tried to get a room on the first floor they was none available but when you book a room at that hotel they don’t say no elevator this is not right " [](https://expedia.ca/Portland-Hotels-Inn-At-St-John-Portland-In-Town.h67481.Hotel-Information) ![Embassy Suites by Hilton Portland Maine](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/6b6e052e_y.jpg) ### Embassy Suites by Hilton Portland Maine 10/10 Excellent "Embassy Suites is always clean with a nice staff and nice breakfast. They allow early check in and late check out whenever they are able to, which helps A LOT! We always prefer the Embassy Suites in Portland " [](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 "The rooms are super clean. And the blackout curtains are amazing. Easy to sleep in. Beds are comfortable. And I highly recommend using the valet parking. There is an extra charge but it is so worth it. " [](https://expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) ![Holiday Inn Portland-By the Bay by IHG](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/4e5dab1b_y.jpg) ### Holiday Inn Portland-By the Bay by IHG 8/10 Good "Always a great place to stay. Could use a bit of an update but good for the price. " [](https://expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/c90266f6_y.jpg) ### Clarion Hotel Portland Airport ME 10/10 Excellent "Excellent " [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Chebeague Island? ### How many historical hotels are there in Chebeague Island? ### What are the most important historical sites and other places in Chebeague Island? ### What is a historic hotel like in Chebeague Island? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Chebeague Island have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Beach Hotel Hotels in Bailey Island ](https://www.expedia.ca/Bailey-Island-Hotels-Beach-Hotel.0-0-d6046825-tBeachHotel.Travel-Guide-Filter-Hotels) - 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