Title: Top Chalets in Cumberland County in 2025 | Expedia.ca [Cumberland County Hotels](https://expedia.ca/Destinations-In-Cumberland-County.d553248635976431833.Hotel-Destinations)[Vacation Rentals in Cumberland County](https://expedia.ca/Destinations-In-Cumberland-County.d553248635976431833.Vacation-Rental-Destinations)[Cumberland County Car Rentals](https://expedia.ca/Destinations-In-Cumberland-County.d553248635976431833.Car-Rental-Destinations)[Cumberland County Vacations](https://expedia.ca/Cumberland-County.d553248635976431833.Destination-Travel-Guides) # Chalets in Cumberland County ## Compare and save ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976431833&startDate=2025-10-10&endDate=2025-10-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976431833&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976431833&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976431833&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Cumberland County ![Portland Head Light which includes rocky coastline, general coastal views and a lighthouse](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/267000/267545-South-Coast-Maine.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Portland [](https://expedia.ca/Portland-Chalets.d181420-aaChalets.Travel-Guide-Accommodation) ![Brunswick featuring a church or cathedral and flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265385-Brunswick-Maine.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brunswick [](https://expedia.ca/Brunswick-Chalets.d7114-aaChalets.Travel-Guide-Accommodation) ![Freeport featuring autumn colours and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/92000/92064-Freeport.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Freeport [](https://expedia.ca/Freeport-Chalets.d180773-aaChalets.Travel-Guide-Accommodation) ![Fort Williams Park featuring hiking or walking and a sunset as well as an individual male](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/266000/266240-South-Coast-Maine.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Cape Elizabeth [](https://expedia.ca/Cape-Elizabeth-Chalets.d55620-aaChalets.Travel-Guide-Accommodation) ![Fort Preble showing wild flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/267000/267550-South-Coast-Maine.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### South Portland [](https://expedia.ca/South-Portland-Chalets.d6769-aaChalets.Travel-Guide-Accommodation) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/483000/483630-bridgton.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Bridgton [](https://expedia.ca/Bridgton-Chalets.d6131432-aaChalets.Travel-Guide-Accommodation) ## Featured Chalets in Cumberland County ![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34340900/34340892/a778a131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34340900/34340892/454f8aca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34340900/34340892/0e31fbde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34350000/34340900/34340892/8e6f7a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury, Spacious, 4 BR Chalet, 1 Minute walk to beach, lakefront, pools, skiing Bridgton 9.4/10 Exceptional (18) "The Chalet was great, large living area and a well stocked kitchen. The screened porch came in handy for entertaining the grand kids. Would definitely recommend this property!" [](https://www.expedia.ca/Bridgton-Hotels-Luxury.h34340892.Hotel-Information) ![Chalet, 5 Bedrooms | Exterior](https://images.trvl-media.com/lodging/92000000/91440000/91432000/91431937/720e0bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, 5 Bedrooms | Dining](https://images.trvl-media.com/lodging/92000000/91440000/91432000/91431937/056d15ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, 5 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/92000000/91440000/91432000/91431937/3419df96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, 5 Bedrooms | Beach](https://images.trvl-media.com/lodging/92000000/91440000/91432000/91431937/b70a07d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Good Times Chalet Limit 19 5 Bedroom Chalet by RedAwning West Bridgton [](https://www.expedia.ca/Bridgton-Hotels-Good-Times-Chalet-Limit-19-5-Bedroom-Chalet.h91431937.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110330000/110320300/110320246/52793942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110330000/110320300/110320246/107ccf5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110330000/110320300/110320246/a761a773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/111000000/110330000/110320300/110320246/2f2df422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3-bedroom chalet in lovely Bridgton 1/4 mile from pleasant mountain Skiing West Bridgton 10/10 Exceptional (1) "Wonderful setting. Clean house. Great firepit! The area where the house is was terrific … this was a weekend together for two uncles and their nephew… could not have been more perfect!" [](https://www.expedia.ca/Bridgton-Hotels-Cozy-3-Bedroom-Chalet-In-Lovely-Bridgton-14-Mile-From-Pleasant-Mountain-Skiing.h110320246.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=2025-10-16&endDate=2025-10-17®ionId=553248635976431833&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FCumberland-County-Chalets.d553248635976431833-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCumberland-County-Chalets.d553248635976431833-aaChalets.Travel-Guide-Accommodation) ## Top Cumberland County Hotel Reviews ![Inn at St John Portland In-Town](//images.trvl-media.com/lodging/1000000/70000/67500/67481/c8f4e76e_y.jpg) ### Inn at St John Portland In-Town 10/10 Excellent "Great place to stay. Would highly recommend " [](https://expedia.ca/Portland-Hotels-Inn-At-St-John-Portland-In-Town.h67481.Hotel-Information) ![Hilton Garden Inn Portland Downtown Waterfront](//images.trvl-media.com/lodging/1000000/930000/920400/920341/0e1014a3_y.jpg) ### Hilton Garden Inn Portland Downtown Waterfront 10/10 Excellent "Nice hotel in a great location " [](https://expedia.ca/Portland-Hotels-Hilton-Garden-Inn-Portland-Downtown-Waterfront.h920341.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 "Our stay at the Regency was very enjoyable, the breakfast was outstanding and the staff's willingness to accommodate any of our requests was terrific. I highly recommend booking a room and then enjoying your stay." [](https://expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![Clarion Hotel Portland](//images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg) ### Clarion Hotel Portland 10/10 Excellent "Front desk guest service was friendly, easy, and reliable. The room was more spacious than I anticipated, although the bathroom was as small as you’d expect. They only have bars of soap for the bathroom. I did a quick trip so I thought it was better than expected. There are noticeable areas that need to be refurbished (like torn curtains) but for a night’s stay it was serviceable." [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.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 "Thanks. Great service" [](https://expedia.ca/Portland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Portland.h23500.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 "Rooms are comfortable and it is very quiet here" [](https://expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information) ![Comfort Inn & Suites Scarborough - Portland](//images.trvl-media.com/lodging/3000000/2220000/2213300/2213298/408a3e09_y.jpg) ### Comfort Inn & Suites Scarborough - Portland 10/10 Excellent "We didn't use facilities other that the morning breakfast which was fine (usual). The room smelled like cigarette smoke (supposedly smoke free). Our room was private and quiet and had all we needed." [](https://expedia.ca/Portland-Hotels-Comfort-Inn-Suites-Scarborough-Portland.h2213298.Hotel-Information) ![Cambria Hotel Portland Downtown-Old Port](//images.trvl-media.com/lodging/78000000/77990000/77981700/77981687/bd99451b_y.jpg) ### Cambria Hotel Portland Downtown-Old Port 10/10 Excellent "From check in to check out, the front desk staff was great every day. Our server in the restaurant made great suggestions for breakfast! Spot on! The $25 resort fee/credit is legit & very easy to use. Great location, room is nice, amenities are fantastic! " [](https://expedia.ca/Portland-Hotels-Cambria-Hotel-Portland-Downtown-Old-Port.h77981687.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 "Our room was very quiet and the view was lovely" [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) ## Find out more about Cumberland County ## Cumberland County Chalets information | Number of reviews | 17 | | --- | --- | | Accommodation | 10 Chalets | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Portland](https://www.expedia.ca/3Star-Portland-Hotels.s30-0-d181420.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Portland](https://www.expedia.ca/4Star-Portland-Hotels.s40-0-d181420.Travel-Guide-Filter-Hotels) - 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