Title: Oakland Chalets from CA $442 | 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)[Oakland Vacation Packages](https://expedia.ca/Oakland.d9160.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KM Moore # Search Chalets in Oakland from CA $442 ![](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 prices for these dates Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Oakland Chalets ![Exterior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/d68aefb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/4e8ed583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/80e692ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/067bcc9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats. Oakland 10/10 Exceptional (3) "The place was so clean and fully stocked. We had a wonderful stay. Five stars!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori S. CA $505 CA $955 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Oakland-Hotels-Lake-Views-HOT-TUB-Central-Location-Walk-To-Coffee.h115182127.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113270000/113266900/113266892/ed8e2b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113270000/113266900/113266892/079c6b5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113270000/113266900/113266892/fb609c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113270000/113266900/113266892/a97f0432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet in the Orchard;Romance, Luxury, Relaxation -Movie theater, Sauna, Hot tub Swanton 10/10 Exceptional (3) "We loved the tranquility we experienced during our stay. They offered amazing amenities and it was beautifully furnished. We especially loved the theater room! We will definitely be staying here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia S. CA $224 CA $442 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Swanton-Hotels-Chalet-In-The-OrchardRomance.h113266892.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/01bb64a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/35e0cad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/56916380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/116dffac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits Davis CA $314 CA $662 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Davis-Hotels-Step-Inside-The-Yellow-Door-Your-Mountain-Chalet-Escape-Awaits.h117931073.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76720000/76714300/76714285/51eaf678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/77000000/76720000/76714300/76714285/w2500h1665x4y4-8f221140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76720000/76714300/76714285/30c40be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76720000/76714300/76714285/w2501h1666x3y3-33be715b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Primo Vista! Spectacular views, Dock Slip, Hot Tub McHenry CA $565 CA $1,482 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/McHenry-Hotels-Primo-Vista-Spectacular-Views.h76714285.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04®ionId=9160&adults=2&lodging=CHALET&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Chalets.d9160-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Chalets.d9160-aaChalets.Travel-Guide-Accommodation) ## Top Oakland Hotel Reviews ![Amazing Central Location! Lakefront! Hot tub/dock!](//images.trvl-media.com/lodging/63000000/62990000/62988900/62988840/3de4819e_y.jpg) ### Amazing Central Location! Lakefront! Hot tub/dock! 10/10 Excellent "Great property. Well-equipped for large families." [](https://expedia.ca/Oakland-Hotels-Amazing-Central-Location-Lakefront-Hot-Tubdock.h62988840.Hotel-Information) ![Cabin in the Woods](//images.trvl-media.com/lodging/93000000/92100000/92092300/92092234/f8871107_y.jpg) ### Cabin in the Woods 10/10 Excellent "Very well appointed rental. Lots of amenities! Really enjoyable vacation rental! " [](https://expedia.ca/Oakland-Hotels-Cabin-In-The-Woods.h92092234.Hotel-Information) ![New: Lakefront Luxury Home with Private Indoor Heated Pool!](//images.trvl-media.com/lodging/101000000/100210000/100201500/100201414/9bf07bdb_y.jpg) ### New: Lakefront Luxury Home with Private Indoor Heated Pool! 10/10 Excellent "This property is incredible. The house is spacious and very nicely appointed. We made use of the indoor pool, the hot tubs, the fire pit, and we caught some fish off the dock. No cable, but we screencast our phones onto the TV in the main room to watch a football game. Everyone was constantly mentioning how great the place was. Also, we ordered some firewood before our stay, so their concierge services are great as well. I enjoyed talking to the people at Red Barns. " [](https://expedia.ca/Oakland-Hotels-New-Lakefront-Luxury-Home-With-Private-Indoor-Heated-Pool.h100201414.Hotel-Information) ![Charming Dog Friendly Cottage w/ Dock & Fire Pit](//images.trvl-media.com/lodging/70000000/69390000/69385600/69385600/dc6a9bbc_y.jpg) ### Charming Dog Friendly Cottage w/ Dock & Fire Pit 10/10 Excellent "Excellent stay, we had a blast with the dogs. Just as advertised. The road was a little daunting to cross, but the picnic table down by the dock made it easy to stay down by the water for the day. Hot tub was great and everything in kitchen worked well (but BYO sugar & K Cups!)" [](https://expedia.ca/Oakland-Hotels-NEW-DOGS-WELCOME-Split-Lake-Front-Home-With-Hot-Tub-And-Fire-Pit.h69385600.Hotel-Information) ![Baja Motel](//images.trvl-media.com/lodging/100000000/99840000/99839500/99839480/bc2fc8ba_y.jpg) ### Baja Motel 10/10 Excellent "10 out of 10. Clean, large room. Very nice staff" [](https://expedia.ca/Oakland-Hotels-Riverside-Suites.h99839480.Hotel-Information) ![The Garrett Inn](//images.trvl-media.com/lodging/15000000/14920000/14910400/14910340/d2b2d172_y.jpg) ### The Garrett Inn 10/10 Excellent "Safe, quiet, clean, and adorable. " [](https://expedia.ca/Cumberland-Hotels-The-Garrett-Inn.h14910340.Hotel-Information) ![Bright condo with Deep Creek Lake views, wood fireplace](//images.trvl-media.com/lodging/29000000/28830000/28827300/28827227/9819ae90_y.jpg) ### Bright condo with Deep Creek Lake views, wood fireplace 10/10 Excellent "This was a very nice getaway. Home away from home. We were able to relax and enjoy each other without feeling like we were in someone else’s home. Shops were close by and the scenes were excellent. There was a problem with the toilet overflowing for the entire time. The TV in the downstairs bedroom didn’t work. We are pleased and will be coming back. We actually wanted to stay an extra night but it was already booked.Thank you for the opportunity to stay in your home. " [](https://expedia.ca/Oakland-Hotels-Bright-Condo-With-Deep-Creek-Lake-Views.h28827227.Hotel-Information) ![The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek](//images.trvl-media.com/lodging/106000000/105960000/105953100/105953075/15a0572e_y.jpg) ### The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek 10/10 Excellent "Cute tiny home with plenty of space in the kitchen and living room for two people. The house is very centrally located so it was no more than 15 mins to get anywhere we wanted to go. I particularly enjoyed the fire pit out back!" [](https://expedia.ca/Oakland-Hotels-The-Tiny-House-Deep-Creek-Lake-Centrally-Located-To-Everything-Deep-Creek.h105953075.Hotel-Information) ![Lakefront, dog friendly, dock slip, hot tub, and fire pit](//images.trvl-media.com/lodging/96000000/95210000/95208700/95208674/7af77293_y.jpg) ### Lakefront, dog friendly, dock slip, hot tub, and fire pit 10/10 Excellent "Our stay at this vacation rental was truly unforgettable for our group of 12! The property is impeccably maintained and spotless. The thoughtful layout of both the home and outdoor spaces made it effortless for us to come together as a group or find quiet moments of relaxation on our own. Personally, I couldn’t get over how incredibly comfortable the beds and bedding were! The location is perfect: peaceful and scenic, while still being close to local attractions and amenities. We especially appreciated the hosts letting us know about the complimentary kayaks, paddleboards, and splash pads available at the dock—those little extras created cherished memories for our kids. This rental and responsiveness of the host went beyond all our expectations. We’re already looking forward to our next visit and wholeheartedly recommend it to anyone hoping to create lasting vacation memories. Thank you for making our getaway so special!" [](https://expedia.ca/Oakland-Hotels-Lakefront.h95208674.Hotel-Information) ## Find out more about Oakland ## Oakland Chalets information | Number of reviews | 5 | | --- | --- | | Accommodation | 8 Chalets | | Lowest Price | CA $442 | | Highest Price | CA $1,482 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in Paradise Point](https://www.expedia.ca/2Star-Paradise-Point-Oakland-Hotels.s20-n553248635976481309-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Westernport](https://www.expedia.ca/4Star-Westernport-Hotels.s40-0-d3000440935.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Mountainside](https://www.expedia.ca/5Star-Mountainside-Oakland-Hotels.s50-n553248635976481730-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sunplace](https://www.expedia.ca/5Star-Sunplace-McHenry-Hotels.s50-n553248635976468730-0.Travel-Guide-Filter-Hotels) - [Family Hotels in Accident](https://www.expedia.ca/Accident-Hotels-Family-Hotel.0-0-d3000421215-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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[Chalets in Swanton](https://www.expedia.ca/Swanton-Chalets.d164144-aaChalets.Travel-Guide-Accommodation) - [Honeymoon Resorts and in Swanton](https://www.expedia.ca/Swanton-Hotels-Honeymoon-Hotels.0-0-d164144-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Swanton Hotels](https://www.expedia.ca/Swanton-Hotels.d164144.Travel-Guide-Hotels) - [Motels in Swanton](https://www.expedia.ca/Swanton-Motels.d164144-aaMotels.Travel-Guide-Accommodation) - [Thayerville Hotels](https://www.expedia.ca/Thayerville-Hotels.d553248635975871934.Travel-Guide-Hotels) - [Vacation Homes in Thayerville](https://www.expedia.ca/Thayerville-Private-Vacation-Homes.d553248635975871934-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Honeymoon Resorts and in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Honeymoon-Hotels.0-n553248635976471573-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Hotels-With-Balconies.0-n553248635976471573-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Hotels-With-Indoor-Pool.0-n553248635976471573-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976471573-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Mountain Hotels in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Mountain-Hotels.0-n553248635976471573-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Wedding-Hotels.0-n553248635976471573-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Winery-Hotel.0-n553248635976471573-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Waterfront Greens](https://www.expedia.ca/Waterfront-Greens-Swanton-Hotels-Winery-Hotel.0-n553248635976482173-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Waterfront Greens Hotels](https://www.expedia.ca/Waterfront-Greens-Swanton-Hotels.0-n553248635976482173-0.Travel-Guide-Filter-Hotels) - [Westernport Hotels](https://www.expedia.ca/Westernport-Hotels.d3000440935.Travel-Guide-Hotels) - [Hotels near Wisp Resort](https://www.expedia.ca/Wisp-Resort-Hotels.0-l6091719-0.Travel-Guide-Filter-Hotels) - [Flights to McHenry](https://www.expedia.ca/Cheap-Flights-To-McHenry.d131592.Travel-Guide-Flights) - [Flights from Westernport](https://www.expedia.ca/lp/flights/3000440935/flights-from-westernport) - [Flights from Barton](https://www.expedia.ca/lp/flights/553248626204850781/flights-from-barton) - [Flights from Luke](https://www.expedia.ca/lp/flights/55806/flights-from-luke) - [Flights from Boston (BOS) to Oakland (ODM)](https://www.expedia.ca/lp/flights/bos/odm/boston-to-oakland) - [Flights from Cleveland (CLE) to Oakland (ODM)](https://www.expedia.ca/lp/flights/cle/odm/cleveland-to-oakland) - [Flights from New York (JFK) to Oakland (ODM)](https://www.expedia.ca/lp/flights/jfk/odm/new-york-to-oakland) - [Deep Creek Lake](https://www.expedia.ca/Deep-Creek-Lake-Maryland.d553248635959734861.Vacation-Attraction) - [Friendsville Vacations](https://www.expedia.ca/Friendsville.d6338432.Destination-Travel-Guides) - [Funland](https://www.expedia.ca/Funland-McHenry.d553248621532660290.Vacation-Attraction) - [Visit Thayerville](https://www.expedia.ca/Thayerville.dx553248635975871934) - [Wisp Resort](https://www.expedia.ca/Wisp-Resort-McHenry.d6091719.Vacation-Attraction) - [Budget Rental Cars in Barton](https://www.expedia.ca/Budget-Car-Rentals-In-Barton.d553248626204850781-c39.Car-Rental-Guide-Suppliers) - [Car rental McHenry](https://www.expedia.ca/Car-Rentals-In-McHenry.d131592.Car-Rental-Guide) - [Book Chalets in Oakland on Expedia.com](https://www.expedia.com/Oakland-Chalets.d9160-aaChalets.Travel-Guide-Accommodation)