Title: Oakland City Vacation Packages & Trips 2026 from CA $922 | 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. ## Top Oakland City Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Motel 6 Owensboro, KY](https://images.trvl-media.com/lodging/1000000/1000000/996300/996265/00eaf050_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 Owensboro, KY CA $922 per person Feb 9 - Feb 12 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Evansville (EVV) 5.6/10 (481 reviews) Staff nice but room just awful so torn up and damaged stuff. Never stay there again Reviewed on Nov 16, 2025 ![Residence Inn by Marriott Evansville East](https://images.trvl-media.com/lodging/1000000/70000/68000/67972/w4000h2662x0y0-c398ced3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residence Inn by Marriott Evansville East CA $987 per person Feb 9 - Feb 12 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Evansville (EVV) 8.6/10 Excellent! (508 reviews) Staff was excellent.we like staying here when we come to town for family . Reviewed on Nov 8, 2025 ![Holiday Inn Express Princeton by IHG](https://images.trvl-media.com/lodging/1000000/120000/119200/119126/2aff9b14_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Princeton by IHG CA $1,002 per person Feb 9 - Feb 12 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Evansville (EVV) 8/10 Very Good! (335 reviews) Breakfast was ok. Hot food was hot and fresh. Breakfast area nice and clean. Staff friendly Room was clean. Common areas and elevator could use deep clean. Reviewed on Dec 7, 2025 ![Comfort Inn Henderson - Evansville South](https://images.trvl-media.com/lodging/1000000/810000/807300/807268/c88db1bc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn Henderson - Evansville South CA $1,016 per person Feb 9 - Feb 12 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Evansville (EVV) 8.2/10 Very Good! (311 reviews) Didn't like that the Coffee maker is in the Bathroom Reviewed on Sep 7, 2025 ![Comfort Inn & Suites Evansville Airport](https://images.trvl-media.com/lodging/1000000/50000/40500/40405/4020e7b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn & Suites Evansville Airport CA $1,007 per person Feb 9 - Feb 12 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Evansville (EVV) 8/10 Very Good! (1,000 reviews) The staff was great really nice folks, the only thing was the furniture of the room, couches, chair desk u name it, was very old and had lots of stains the chair was all peeled, floors had some stains too they just need to remodel and tune up the place a lil more. Reviewed on Dec 11, 2025 ## 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 CA $133 CA $150 total Jan 18 - Jan 19, 2026 includes taxes & fees 7.6/10 Good! (6 reviews) The room was excellent and very clean. Staff on site was very professional and courteous! Reviewed on Nov 22, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=117625584&PinnedHotelID=117625584&HadPinnedHotel=true®ionId=6283924) ![Golf Course Views: Oakland City Retreat](https://images.trvl-media.com/lodging/113000000/112280000/112275800/112275739/2948679c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Golf Course Views: Oakland City Retreat Oakland City IN [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=112275739&PinnedHotelID=112275739&HadPinnedHotel=true®ionId=6283924) [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=112275739&PinnedHotelID=112275739&HadPinnedHotel=true®ionId=6283924) ![Half-mi to Oakland City Golf Club: Sleek Apartment](https://images.trvl-media.com/lodging/113000000/112280000/112275800/112275729/d26bd117_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Half-mi to Oakland City Golf Club: Sleek Apartment Oakland City IN [Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=112275729&PinnedHotelID=112275729&HadPinnedHotel=true®ionId=6283924) [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=112275729&PinnedHotelID=112275729&HadPinnedHotel=true®ionId=6283924) [See all 179 properties in Oakland City](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F12%2F2025&endDate=20%2F12%2F2025®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