Title: Cumberland County Vacation Packages 2026 from $395 | Expedia.com [Cumberland County Hotels](https://expedia.com/Destinations-In-Cumberland-County.d553248635976431833.Hotel-Destinations)[Vacation Rentals in Cumberland County](https://expedia.com/Destinations-In-Cumberland-County.d553248635976431833.Vacation-Rental-Destinations)[Cumberland County Flights](https://expedia.com/Destinations-In-Cumberland-County.d553248635976431833.Flight-Destinations)[Car Rentals in Cumberland County](https://expedia.com/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 Vacations & Trips from $395 ## Book a Hotel + Flight or Car together to unlock savings Photo by Rob Gosse ### 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.com/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.com/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 destinations in Cumberland County ![Brunswick showing 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.com/Brunswick.d7114.Destination-Travel-Guides) ![Freeport featuring a city and fall colors](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.com/Freeport.d180773.Destination-Travel-Guides) ![Fort Williams Park showing a sunset and hiking or walking 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.com/Cape-Elizabeth.d55620.Destination-Travel-Guides) ![Fort Preble featuring wildflowers](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.com/South-Portland.d6769.Destination-Travel-Guides) ![Bridgton](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.com/Bridgton.d6131432.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.com/Scarborough.d6809.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/6046fecae1367ea61a2fe990e800fee2.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Raymond [](https://expedia.com/Raymond.d183293.Destination-Travel-Guides) ![Bridgton](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/483000/483630-bridgton.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Naples [](https://expedia.com/Naples.d183286.Destination-Travel-Guides) ## The Latest Cumberland County Vacation Packages Price found within the past 48 hours. Click for updated prices. ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### D. Hotel Suites & Spa Save 100% on your flight $395 per person May 2 - May 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.4/10 Exceptional! (2,242 reviews) Great clean room that was nice and warm on the cold day. Loved the fireplace in the living area and the bed was very comfortable and cozy. Great value for the space we got! Reviewed on Feb 8, 2026 ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Revolution Hotel South End Save 100% on your flight $674 per person May 2 - May 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9/10 Wonderful! (2,241 reviews) A bit disappointed in the cleanliness of my room. Dusty areas around the bed and hair on my sheets, which freaked me out. Staff was not knowledgeable about parking options. Restaurant was fantastic! Reviewed on Feb 8, 2026 ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Charles Hotel West Cambridge Save 100% on your flight $763 per person Mar 12 - Mar 16 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 9.4/10 Exceptional! (1,003 reviews) Room very well appointed and gym was the stand out Reviewed on Jan 25, 2026 ![Boston Lodge and Suites](https://images.trvl-media.com/lodging/22000000/21340000/21333100/21333029/d2b7feac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Lodge and Suites Dorchester Save 100% on your flight $947 per person May 2 - May 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 8.4/10 Very Good! (188 reviews) Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available. Reviewed on Nov 10, 2025 ![Eurostars The Boxer](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/db81308e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars The Boxer West End Save 100% on your flight $835 per person May 2 - May 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Boston (BOS) 8.6/10 Excellent! (1,337 reviews) Thank you for the cool corner suite on the 9th floor! We stayed over after attending a Bruins game. Short stay but nice place. Good location for our adventures. We’ll stay again if when we are back in Boston! Ty Reviewed on Jan 29, 2026 ## Find the Best Cumberland County Vacation Packages ## Cumberland County Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Portland Intl. Jetport Airport (PWM) | | Top Sights | [Sebago Lake](https://www.expedia.com/Sebago-Lake-Maine.d553248635056397238.Vacation-Attraction), [Higgins Beach](https://www.expedia.com/Higgins-Beach-Maine.d6326755.Vacation-Attraction) and [East End Beach](https://www.expedia.com/East-End-Beach-East-End.d6326357.Vacation-Attraction) | ## 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 $77 nightly $85 total Feb 19 - Feb 20 Total with taxes and fees 8/10 Very Good! (1,351 reviews) Great location great staff everything functioned. Reviewed on Feb 6, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%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 $147 nightly $163 total Feb 11 - Feb 12 Total with taxes and fees 9.2/10 Wonderful! (1,751 reviews) Wonderful stay! Reviewed on Feb 7, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%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 $127 nightly $141 total Mar 1 - Mar 2 Total with taxes and fees 9.4/10 Exceptional! (1,578 reviews) The room was impeccable, the restaurant was delicious and perfect location Reviewed on Jan 29, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=553248635976431833) [See all 2,152 properties in Cumberland County](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F9%2F2026&endDate=2%2F10%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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) Explore a world of travel with Expedia ## Other vacations you might like - Top cities in Cumberland County - Vacations and getaways similar to Cumberland County - Best vacation destinations by month - [South Portland Vacations ](https://expedia.com/South-Portland.d6769.Destination-Travel-Guides) - [Scarborough Vacations ](https://expedia.com/Scarborough.d6809.Destination-Travel-Guides) - [Raymond Vacations ](https://expedia.com/Raymond.d183293.Destination-Travel-Guides) - [Freeport Vacations ](https://expedia.com/Freeport.d180773.Destination-Travel-Guides) - [Brunswick Vacations ](https://expedia.com/Brunswick.d7114.Destination-Travel-Guides) - [Cape Elizabeth Vacations ](https://expedia.com/Cape-Elizabeth.d55620.Destination-Travel-Guides) - [Bridgton Vacations ](https://expedia.com/Bridgton.d6131432.Destination-Travel-Guides) - [Windham Vacations ](https://expedia.com/Windham.d10053.Destination-Travel-Guides) - [Falmouth Vacations ](https://expedia.com/Falmouth.d6336429.Destination-Travel-Guides) - [Peaks Island Vacations ](https://expedia.com/Peaks-Island.d6151240.Destination-Travel-Guides) - [Naples Vacations ](https://expedia.com/Naples.d183286.Destination-Travel-Guides) - [Sebago Vacations ](https://expedia.com/Sebago.d6327259.Destination-Travel-Guides) - [New Hampshire Vacations ](https://expedia.com/New-Hampshire.d231.Destination-Travel-Guides) - [January Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-january) - [February Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-february) - [March Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-march) - [April Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-april) - [May Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-may) - [June Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-june) - [July Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-july) - [August Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-august) - [September Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-september) - [October Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-october) - [November Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-november) - [December Vacations and Deals ](https://www.expedia.com/lp/b/where-to-go/vacations-december) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.