Title: Oakland Hills Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,279 Expedia.ca [Hotels in Oakland Hills](https://expedia.ca/Oakland-Hills-Rotonda-West-Hotels.0-n553248635976470746-0.Travel-Guide-Filter-Hotels)[Flights to Rotonda West](https://expedia.ca/Cheap-Flights-To-Rotonda-West.d6341253.Travel-Guide-Flights)[Oakland Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland-Hills.d553248635976470746.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland Hills 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 ## Top Holiday Package Deals in Oakland Hills Price found within the past 48 hours. Click for updated prices. ![Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton](https://images.trvl-media.com/lodging/102000000/101510000/101505800/101505781/a4bc3bc9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton CA $1,279 per person Mar 21 - Mar 28 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Punta Gorda Airport (PGD) 9.2/10 Wonderful! (1,612 reviews) Room was nice but next to ice machine and elevators and no flexibility by staff to move us. Also supposed to be harbour view but only thing could really see was an old rooftop of the hotel. Took an hour and a half for a drink to be delivered at the rooftop bar. Hot tub was broke and no staff seemed to care Reviewed on Feb 10, 2026 ## Where to stay in Oakland Hills Find the best Oakland Hills areas and neighborhoods for the activities you enjoy most. [Learn more about Oakland Hills](https://expedia.ca/Rotonda-West-Oakland-Hills.dx553248635976470746) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Pine Valley Pine Valley might not have many top sights, but Don Pedro Island Beach and Little Gasparilla Island Beach are two attractions nearby that you can check out. [Find hotel + flight trips in Pine Valley](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pine%20Valley&DestID=553248635976470822&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Golf course on ocean shore in southwest Florida. Seaside golfing field in Boca Grande](https://images.trvl-media.com/place/553248635976471231/3ccc50c9-4fe5-4edb-aacc-d9a34bf1a2a5.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### White Marsh Though White Marsh might not have many top sights, you can venture to the surrounding area to see attractions like Don Pedro Island Beach and Little Gasparilla Island Beach. [Find hotel + flight trips in White Marsh](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=White%20Marsh&DestID=553248635976471231&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Pebble Beach Pebble Beach might not have many top sights, but Don Pedro Island Beach and Stump Pass Beach State Park are two attractions nearby that you can check out. [Find hotel + flight trips in Pebble Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pebble%20Beach&DestID=553248635976480933&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Rotonda Heights While there might not be top attractions in Rotonda Heights, you can explore the larger area and discover places like Don Pedro Island Beach and Stump Pass Beach State Park. [Find hotel + flight trips in Rotonda Heights](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Rotonda%20Heights&DestID=553248635976469318&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Broadmoor While there might not be top attractions in Broadmoor, you can explore the larger area and discover places like Don Pedro Island Beach and Don Pedro Island State Park. [Find hotel + flight trips in Broadmoor](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Broadmoor&DestID=553248635976479272&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Oakland Hills Hotel Deals ![Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton](https://images.trvl-media.com/lodging/102000000/101510000/101505800/101505781/a4bc3bc9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton 5500 Sunseeker Way Punta Gorda FL Fully refundableReserve now, pay when you stay CA $191 CA $282 total Mar 12 - Mar 13 includes taxes & fees 9.2/10 Wonderful! (1,825 reviews) Beautiful Hotel Reviewed on Feb 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=101505781&PinnedHotelID=101505781&HadPinnedHotel=true®ionId=553248635976470746) ![The Suites at Fishermen’s Village- 2 Bedroom Suites](https://images.trvl-media.com/lodging/53000000/52080000/52074900/52074809/ba7422d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Suites at Fishermen’s Village- 2 Bedroom Suites 1200 W Retta Esplanade Punta Gorda FL Fully refundableReserve now, pay when you stay CA $390 CA $437 total Feb 22 - Feb 23 includes taxes & fees 9.8/10 Exceptional! (1,100 reviews) The room was very clean, spacious, had a full kitchen, great view, and was the second floor of Fisherman's Village, which has several stores and a few restaurants. The staff was also very courteous. Reviewed on Feb 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=52074809&PinnedHotelID=52074809&HadPinnedHotel=true®ionId=553248635976470746) ![Days Inn by Wyndham Port Charlotte/Punta Gorda](https://images.trvl-media.com/lodging/1000000/10000/6600/6518/3b6904ff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Port Charlotte/Punta Gorda 1941 Tamiami Trl Port Charlotte FL Fully refundableReserve now, pay when you stay CA $166 CA $186 total Feb 15 - Feb 16 includes taxes & fees 7.6/10 Good! (1,008 reviews) Courteous staff, clean room Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=6518&PinnedHotelID=6518&HadPinnedHotel=true®ionId=553248635976470746) [See all 6,129 properties in Oakland Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F02%2F2026&endDate=14%2F02%2F2026®ionId=553248635976470746) 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) ## Frequently asked questions ### How much does an Oakland Hills vacation package cost? ### How do I get a cheap travel package to Oakland Hills? ### What are the top hotels in Oakland Hills? ### How far in advance should I book my Oakland Hills vacation? ### What does an Expedia Oakland Hills travel package include? ### What should I know before booking an Oakland Hills travel package? ### Can I choose my airline with an Oakland Hills Expedia vacation package? ### If I'm not able to travel, can I cancel my Oakland Hills vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.