Title: Book the Best Hotels with BARS in Chebeague Island in 2025 | 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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Bar in Chebeague Island, ME from CA $138 ![](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 Hotels with Bar ## Top Chebeague Island Hotels with Bar ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23800/23779/b95e6193.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) ![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) ![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 (339) "Good location and reasonable price for a clean room and all you need if your just staying a night or two. I would book this hotel again." ![](https://a.travel-assets.com/egds/marks/flags/ca.svg) Troy CA $126 CA $138 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information) ![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/d7b085e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/52000000/51270000/51266300/51266260/99e8f1d5.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) ### The Harraseeket Inn & Event House Freeport Downtown Freeport 9.4/10 Exceptional (831) "Within walking distance of many restaurants and L L Bean….a really nice place to stay" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $167 CA $182 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Harraseeket-Inn.h51266260.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/0e1014a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/45722919.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) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/930000/920400/920341/50a23de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Portland Downtown Waterfront Downtown Portland 9.2/10 Wonderful (1016) "Great location, easy valley parking, clean rooms, friendly staff" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $154 CA $171 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/cbc24127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/6b6e052e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Embassy Suites by Hilton Portland Maine Portland 9.4/10 Exceptional (1129) "Very nice hotel, clean, comfortable and breakfast was excellent." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $131 CA $145 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/b4e33349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/ea594a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/06fb9956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Bay View](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/bc24f75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Portland Downtown - Old Port Square Downtown Portland 8.8/10 Excellent (1220) "Great hotel in great location." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $163 CA $180 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Honeymoon Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/w7354h4909x8y4-ca190742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/171efe7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/e9f78f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Portland Harbor Hotel Downtown Portland 9.2/10 Wonderful (1628) "Loved our visit! " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $161 CA $232 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/3ba35403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/afa1cd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/ec896d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/f8d50db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brunswick Hotel Brunswick 9.2/10 Wonderful (859) "Lovely place to stay." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jodie CA $177 CA $192 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boothbay-Harbor-Hotels-The-Brunswick-Hotel.h4449120.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/fae57c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/3250b622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Harbour View](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/133f948c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/915b9bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Portland Downtown-Old Port East Bayside 9.4/10 Exceptional (1108) "Excellent hotel " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $154 CA $208 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-Cambria-Hotel-Portland-Downtown-Old-Port.h77981687.Hotel-Information) ![Tapas bar](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514704/f9c45283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tapas bar](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514704/37ad9881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514704/dd9cace5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514704/59ee2cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel Portland Downtown/Waterfront, ME East Bayside 9.2/10 Wonderful (1008) "Excellent hotel close to Burlington and Green Mountain attractions. Excellent dining option - Farmhouse Tap & Grill." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Arkadiy CA $150 CA $166 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Portland-Hotels-AC-Hotel-By-Marriott-Portland-DowntownWaterfront.h22514704.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/21df5bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/e38717ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/2cd1b596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Portland Regency Hotel & Spa Downtown Portland 9.4/10 Exceptional (1477) "Loved this spot " ![](https://a.travel-assets.com/egds/marks/flags/ca.svg) Anita CA $197 CA $219 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.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=2025-11-01&endDate=2025-11-02®ionId=6046986&adults=2&amenities=BAR&sort=RECOMMENDED&openPlayBack=true) ## Top Chebeague Island Hotel Reviews ![Portland Harbor Hotel](//images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg) ### Portland Harbor Hotel 10/10 Excellent "My wife loved the shower! Hot and heavy pouring. Walkable to wharfs, shopping and restaurants. Large room and very large bathroom." [](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.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 "Nice hotel in a good location. Friendly staff. Clean room." [](https://expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.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 "Perfect location, great staff, very quiet, comfortable beds, very clean." [](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![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) ![Comfort Inn Airport](//images.trvl-media.com/lodging/1000000/30000/27100/27041/e9231d1b_y.jpg) ### Comfort Inn Airport 10/10 Excellent "The airport shuttle was great. The rooms were clean and the front desk was helpful. I would stay here again." [](https://expedia.ca/Portland-Hotels-Comfort-Inn-Airport.h27041.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 "Super friendly staff, clean, comfortable and conveniently located! The breakfast was especially good and the staff couldn't have been friendlier! I would absolutely go back!" [](https://expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.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) ## Frequently asked questions ### Searching for hotels with bars in Chebeague Island? > Though you might not find a hotel in Chebeague Island well-known for its bar, you will find 9 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're in the area, consider a visit to Wolfe's Neck Woods State Park and Bailey Island Bridge. ### What are the best hotels with bars in Chebeague Island? > Below are some of top hotels with bars in and around Chebeague Island: [Portland Harbor Hotel](https://www.expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and 3 coffee shops. [Germaine Inn South Portland](https://www.expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information): Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. [Fireside Inn & Suites Portland](https://www.expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information): Hotel with restaurant. Enjoy the 2 bars, free WiFi, and full-service spa. [Clarion Hotel Portland Airport ME](https://www.expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information): Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. [LivAway Suites Portland-Scarborough](https://www.expedia.ca/Scarborough-Hotels-LivAway-Suites-Portland-Scarborough.h116230622.Hotel-Information): Enjoy the bar, free WiFi, and breakfast. ### What is there to do in Chebeague Island? > If you have time to explore, consider visiting Wolfe's Neck Woods State Park, Bailey Island Bridge, and Casco Bay, and then find a cozy spot for a nightcap. Other places to see in the area include Sand Beach and Harrington House. ### When is the best time to visit Chebeague Island? > Visiting local bars in Chebeague Island is more fun when you know what the weather holds. These rainfall averages and temperatures can help you decide the best time for bar hopping. 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 Chebeague Island are January, March, February, and December, with each month seeing an average of 7 inches of snowfall. ### How can I get to Chebeague Island and around the area? > You might want to make the most of these transportation choices in and around Chebeague Island: Fly into Portland Intl. Jetport Airport (PWM), which is located 12.1 mi (19.4 km) from the city center. Otherwise, you can search for flights to Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 23 mi (37.1 km) away. 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