Title: Oakland City Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Oakland City](https://expedia.ca/Oakland-City-Hotels.d6283924.Travel-Guide-Hotels)[Vacation Rentals in Oakland City](https://expedia.ca/Oakland-City-Vacation-Rentals.d6283924.Travel-Guide-VacationRentals)[Oakland City Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland-City.d6283924.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland City 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 City Vacation Our vacation packages to Oakland City let you customize your own adventure. Tailor your getaway to suit your needs and interests and make every moment count in this fabulous city. Need some inspiration on what to see or do first during your trip to Oakland City? Check off well-known attractions such as [Oakland City University](https://www.expedia.ca/Oakland-City-University-Oakland-City.d6281559.Vacation-Attraction). Your perfect Oakland City vacation is only clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style. ![](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_6283924) ## Ready to book your vacation to Oakland City? Choose your dates ## Oakland City Hotel Deals ![Oakland Courtyard](https://images.trvl-media.com/lodging/118000000/117630000/117625600/117625584/86a3f489_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oakland Courtyard 1000 W Morton St, Oakland City Oakland City IN 8.4/10 Very Good! (10 reviews) Room very clean and spacious. Bed was comfortable. Reviewed on Feb 7, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=117625584&PinnedHotelID=117625584&HadPinnedHotel=true®ionId=6283924) [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=117625584&PinnedHotelID=117625584&HadPinnedHotel=true®ionId=6283924) ![Drury Inn & Suites Evansville East](https://images.trvl-media.com/lodging/1000000/120000/116600/116545/2ba5f829_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Drury Inn & Suites Evansville East 100 Cross Pointe Blvd Evansville IN Fully refundableReserve now, pay when you stay CA $145 CA $167 total Mar 1 - Mar 2 includes taxes & fees 9.2/10 Wonderful! (1,005 reviews) The new manager is very friendly as is the rest of the staff. They do a great job! We will be back soon. Reviewed on Feb 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=116545&PinnedHotelID=116545&HadPinnedHotel=true®ionId=6283924) ![La Quinta Inn & Suites by Wyndham Evansville](https://images.trvl-media.com/lodging/1000000/50000/42500/42483/29ca343a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Evansville 8015 East Division Street Evansville IN Fully refundableReserve now, pay when you stay CA $104 CA $119 total Mar 8 - Mar 9 includes taxes & fees 8.6/10 Excellent! (1,006 reviews) I had a very nice stay at the LaQuinta from Feb 13 thru the morning of the 15th.Staff was excellent and attentive to my needs. Only negative comment was that my room was not attended to Saturday morning by the housekeeping staff. Reviewed on Feb 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=42483&PinnedHotelID=42483&HadPinnedHotel=true®ionId=6283924) [See all 181 properties in Oakland City](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F02%2F2026&endDate=24%2F02%2F2026®ionId=6283924) 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) ### Discover the most popular places to visit in Oakland City #### Oakland City University Explore the campus of Oakland City University, during your trip to Oakland City. [](https://expedia.ca/Oakland-City-University-Oakland-City.d6281559.Vacation-Attraction) ## 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