Title: Oakland Vacation Packages & Trips 2026 from CA $910 | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d9160.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d9160.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d9160.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9160/8b60b0ad-d1dd-4e6b-8fc4-a386a87d5f65.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by KM Moore - ## 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 When a fun city break is calling, answer it with a vacation package to Oakland. The neighborhood of Blakeslee, which is great for nature, watersports and views, makes a wonderful base for your adventures. If going to see the sights is a priority during your trip to Oakland, be sure to swing by popular attractions like [Swallow Falls State Park](https://www.expedia.ca/Swallow-Falls-State-Park-Oakland.d553248621532660285.Vacation-Attraction) and [Herrington Manor State Park](https://www.expedia.ca/Herrington-Manor-State-Park-Cumberland.d637198051668946944.Vacation-Attraction). No matter your travel plans or the size of your budget, putting together a tailored Oakland vacation is a cinch with Expedia. ## Top Oakland Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Microtel Inn & Suites by Wyndham Hazelton/Bruceton Mills](https://images.trvl-media.com/lodging/2000000/1710000/1705900/1705851/0efde2c4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Microtel Inn & Suites by Wyndham Hazelton/Bruceton Mills CA $910 per person Apr 18 - Apr 25 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Morgantown (MGW) 8.2/10 Very Good! (1,002 reviews) Outstanding front desk staff! Reviewed on Jan 25, 2026 ![VVS - Very Very Special](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011849/9108af02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### VVS - Very Very Special CA $6,835 per person Apr 18 - Apr 25 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Morgantown (MGW) No reviews ![St. Bart's Retreat](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011467/a069023b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### St. Bart's Retreat CA $4,832 per person Apr 18 - Apr 25 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Morgantown (MGW) No reviews ![Nature's Retreat](https://images.trvl-media.com/lodging/77000000/76020000/76010400/76010311/e7cd11f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nature's Retreat Blakeslee CA $3,479 per person Apr 18 - Apr 25 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Morgantown (MGW) No reviews ![Bear Hollow Lodge](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/a709d25a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bear Hollow Lodge CA $3,583 per person Apr 18 - Apr 25 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Morgantown (MGW) No reviews ## Ready to book your vacation to Oakland? Choose your dates ## Oakland Hotel Deals ![The Garrett Inn](https://images.trvl-media.com/lodging/15000000/14920000/14910400/14910340/d2b2d172_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Garrett Inn 17848 Garrett Highway Oakland MD CA $146 CA $167 total Feb 11 - Feb 12 includes taxes & fees 9.6/10 Exceptional! (415 reviews) Clean, quiet, nice amenities - nice! Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=14910340&PinnedHotelID=14910340&HadPinnedHotel=true®ionId=9160) ![In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,](https://images.trvl-media.com/lodging/90000000/89150000/89146100/89146013/2fb0c438_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp, Oakland MD 8/10 Very Good! (69 reviews) Host was great!! Got back to me right away when I had a question. We all had a great time! Great location!! Reviewed on Jan 18, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=89146013&PinnedHotelID=89146013&HadPinnedHotel=true®ionId=9160) [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=89146013&PinnedHotelID=89146013&HadPinnedHotel=true®ionId=9160) ![Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp](https://images.trvl-media.com/lodging/105000000/104790000/104788500/104788464/f498bb48_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp Oakland MD 9.4/10 Exceptional! (16 reviews) My family and I, including our dog Harley, had a great stay. Terry was an amazing host. We had a weather related issue and she was super responsive and extremely helpful. This was our second stay at this property. It fits our needs and was perfect for a few days of skiing and playing in the snow. ... Reviewed on Jan 5, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=104788464&PinnedHotelID=104788464&HadPinnedHotel=true®ionId=9160) [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=104788464&PinnedHotelID=104788464&HadPinnedHotel=true®ionId=9160) [See all 821 properties in Oakland](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026®ionId=9160) 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