Title: Oakland Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d140470.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d140470.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d140470.Car-Rental-Guide) ![](https://images.trvl-media.com/place/140470/42f41efd-d0d8-495c-9b9e-35b09539ac39.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Oakland Vacation There's no better way to embark on an adventure than with one of our vacation packages to Oakland. The rich history and eclectic style are just a couple of the convincing reasons to visit this captivating city. Make your trip to Oakland even more fun and exciting by going sightseeing. [Colby College](https://www.expedia.ca/Colby-College-Waterville.d6182152.Vacation-Attraction), [Belgrade Lakes Chain](https://www.expedia.ca/Belgrade-Lakes-Chain-Augusta.d553248635976193929.Vacation-Attraction) and [Waterville Opera House](https://www.expedia.ca/Waterville-Opera-House-Waterville.d6173839.Vacation-Attraction) are among the leading attractions worth exploring. Expedia can help you escape the everyday. Tailor your vacation to Oakland to match your travel style, whatever that may look like. ## Ready to book your vacation to Oakland? Choose your dates ## Oakland Hotel Deals ![Cozy Long Pond Cottage: private mooring & shared dock](https://images.trvl-media.com/lodging/100000000/99730000/99724000/99723919/b794f39d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Long Pond Cottage: private mooring & shared dock Rome ME 9.8/10 Exceptional! (21 reviews) The cottage was beautiful. Everything inside was new or in new condition. The host was also excellent. During our stay we conversed like we were old friends. Cottage was surprisingly well stocked. I would literally want to stay there again. Reviewed on Jan 17, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=99723919&PinnedHotelID=99723919&HadPinnedHotel=true®ionId=140470) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=99723919&PinnedHotelID=99723919&HadPinnedHotel=true®ionId=140470) ![Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore](https://images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/20d8d18f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore Oakland ME CA $194 CA $376 total Feb 16 - Feb 17 includes taxes & fees 9.8/10 Exceptional! (18 reviews) Yes, thank you again Diane Reviewed on Jan 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=107340207&PinnedHotelID=107340207&HadPinnedHotel=true®ionId=140470) ![Charming Guest House on Farm - Pets Welcome](https://images.trvl-media.com/lodging/114000000/113530000/113522100/113522019/4b703bf0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming Guest House on Farm - Pets Welcome Oakland ME CA $254 CA $485 total Feb 8 - Feb 9 includes taxes & fees 10/10 Exceptional! (8 reviews) It was a great stay. The house is very comfortable Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=113522019&PinnedHotelID=113522019&HadPinnedHotel=true®ionId=140470) [See all 523 properties in Oakland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=140470) 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) ## Explore a world of travel with Expedia \* 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