Title: Cumberland County Vacations & Trips 2026 from CA $861 | 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) ![](https://images.trvl-media.com/place/55620/ffa97ca5-f2ba-41f5-85a2-a60d70c859b1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cumberland County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Rob Gosse - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ### Your Cumberland County Vacation When adventure calls, answer it with a tailor-made vacation package to Cumberland County. Wherever your journey takes you and whatever you have planned, get set to discover a destination with so much to offer. With so many things to explore on a trip to Cumberland County, it can be hard to know where to start. Kick off your journey in [Portland](https://www.expedia.ca/Portland.d181420.Destination-Travel-Guides) at Maine Mall and Thompson's Point — two popular attractions here. Another city to add to your itinerary is [Brunswick](https://www.expedia.ca/Brunswick.d7114.Destination-Travel-Guides). Don't miss Maine Street and LL Bean Flagship Store. From the instant you book your Cumberland County vacation to the second you come back home, Expedia will take care of you every step of the way. ## Top vacation destinations 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.d181420.Destination-Travel-Guides) ![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.d7114.Destination-Travel-Guides) ![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.d180773.Destination-Travel-Guides) ![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.d6769.Destination-Travel-Guides) ![Scarborough featuring a coastal town and general coastal views as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/267000/267649-Scarborough-Portland.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Scarborough [](https://expedia.ca/Scarborough.d6809.Destination-Travel-Guides) ## Top Cumberland County Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Studio Allston Hotel](https://images.trvl-media.com/lodging/23000000/22760000/22757100/22757092/a522d616_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Studio Allston Hotel Brighton CA $861 per person May 7 - May 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.6/10 Excellent! (1,175 reviews) Staff was friendly. Room was clean Reviewed on Feb 5, 2026 ![The Boston Hotel](https://images.trvl-media.com/lodging/101000000/100140000/100136300/100136229/54a79fec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Boston Hotel Brighton CA $1,260 per person May 7 - May 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 7.4/10 Good! (802 reviews) Clean room, staff was great, chill and easy to access. Good price as well! Reviewed on Feb 9, 2026 ![Fairmont Copley Plaza, Boston](https://images.trvl-media.com/lodging/1000000/30000/26000/25981/ea541272_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Copley Plaza, Boston Back Bay CA $1,896 per person Apr 4 - Apr 11 found 11 hours ago Roundtrip flight included Halifax (YHZ) to Boston (BOS) 9/10 Wonderful! (1,094 reviews) The hotel was beautiful and the staff friendly and welcoming, Reviewed on Feb 15, 2026 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,458 per person May 1 - May 3 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_553248635976431833) ## Cumberland County Hotel Deals ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clarion Hotel Portland Airport ME 1230 Congress St Portland ME Fully refundableReserve now, pay when you stay CA $105 CA $116 total Feb 19 - Feb 20 includes taxes & fees 8/10 Very Good! (1,354 reviews) Was nice Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F02%2F2026&endDate=20%2F02%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=553248635976431833) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Harbor Hotel 468 Fore Street Portland ME Fully refundableReserve now, pay when you stay CA $144 CA $212 total Mar 15 - Mar 16 includes taxes & fees 9.2/10 Wonderful! (1,752 reviews) Nice decor and amenities (pantry) Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=898621&PinnedHotelID=898621&HadPinnedHotel=true®ionId=553248635976431833) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Regency Hotel & Spa 20 Milk Street Portland ME Fully refundableReserve now, pay when you stay 9.4/10 Exceptional! (1,584 reviews) Loved the sauna / spa! Will definitely make this a regular getaway destination. Reviewed on Feb 9, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=553248635976431833) [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=553248635976431833) [See all 2,156 properties in Cumberland County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F02%2F2026&endDate=17%2F02%2F2026®ionId=553248635976431833) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Cumberland County vacation package cost? ### How do I get a cheap travel package to Cumberland County? ### Where should I stay in Cumberland County? ### What are the top hotels in Cumberland County? ### How far in advance should I book my Cumberland County vacation? ### What does an Expedia Cumberland County travel package include? ### What should I know before booking a Cumberland County travel package? ### Can I choose my airline with a Cumberland County Expedia vacation package? ### If I'm not able to travel, can I cancel my Cumberland County vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app