Title: Book the Best CHEAP Hotels in Oakland, Winter Garden - Oakland Cheap Hotels | Expedia.ca [Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6360404.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6360404.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/a8a5cc3452c5ce939a38ef30d23f8715.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Gregg Yutko # Find Cheap Hotels in Oakland, Winter Garden ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oakland Cheap Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6360404&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Cheap Hotels ## Top Oakland Hotel Reviews ![Holiday Inn Resort Kissimmee by the Parks by IHG](//images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg) ### Holiday Inn Resort Kissimmee by the Parks by IHG 10/10 Excellent "Noisy family next door with multiple small children." [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![DoubleTree by Hilton at the Entrance to Universal Orlando](//images.trvl-media.com/lodging/1000000/10000/5400/5398/4997b5df_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 10/10 Excellent "Great" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![CoCo Key Hotel and Water Resort ](//images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2_y.jpg) ### CoCo Key Hotel and Water Resort  10/10 Excellent "Very friendly staff and budget friendly hotel with great water park and restaurants close by." [](https://expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)  ![DoubleTree by Hilton Hotel Orlando at SeaWorld](//images.trvl-media.com/lodging/1000000/20000/18900/18874/69019073_y.jpg) ### DoubleTree by Hilton Hotel Orlando at SeaWorld 10/10 Excellent "My weekend stay was awesome, my wife and I loved the hotel the moment we entered the staff was very helpful and pleasant. We had slight challenge in our room and it was corrected in a timely manner. We will definitely be back!!" [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Hotel-Orlando-At-SeaWorld.h18874.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Plenty of swimming areas for kids and volleyball area. I especially loved the calming lake view from our balcony." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "It was nice I saw kids enjoying the lazy river on one pool and the slide had kids playing with no problem. I have 7 kids and I think they would really enjoy this resort." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Rosen Inn Lake Buena Vista](//images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 10/10 Excellent "Staff is always friendly and rooms are always clean! My go to hotel for an off property Disney trip! " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Absoluteky enjoyed my week there, can not wait to come back. Perfect for families and solo travelers :) " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Very nice property for couples or families." [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ## Frequently asked questions ### What is Oakland like for travelers on a budget? > Check out discount places to stay in Oakland on Expedia.com and book a vacation that sticks within your budget. You can scroll through a variety of hotels and other types of accommodation with Member Prices to score great deals. Guided by our site's helpful page filters, you can limit results by price per night, or by amenities that customers often look for like free breakfast and free airport transportation. The location filters are a great way to see affordable options near specific attractions, such as Oakland Nature Preserve. While you browse, use the heart button to save your favorites so that it's easy to find them when you're ready to book. Need a car or a flight too? Choose from the Bundle and Save travel packages and discover huge discounts by booking transportation at the same time. ### What is there to see and do in Oakland? > You won't have to spend a fortune to find places to visit in Oakland. You can budget for the popular local attractions that are highest on your list, such as Magic Kingdom® Park and Walt Disney World® Resort, and choose other low-cost activities to fill your itinerary. Check out the area's cultural spots like Titanic the Experience and Pirate's Dinner Adventure, or get outdoors at Oakland Nature Preserve. ### How can I get to Oakland and get around on a budget? > Checking out these ways to get around Oakland can help keep you on budget. The most convenient airport is 21.4 mi (34.5 km) from the center in Leesburg, FL (LEE-Leesburg Intl.). If that doesn't suit your budget, you can look into flights to Orlando Intl. Airport (MCO), which is 21.5 mi (34.6 km) away. 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