Title: The Best Oakland, MD Chalets from $450 | Expedia.com [Oakland Travel Guide](https://expedia.com/Oakland.dx9160)[Hotels in Oakland](https://expedia.com/Oakland-Hotels.d9160.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.com/Oakland-Vacation-Rentals.d9160.Travel-Guide-VacationRentals)[Flights to Oakland](https://expedia.com/Cheap-Flights-To-Oakland.d9160.Travel-Guide-Flights)[Car Rentals in Oakland](https://expedia.com/Car-Rentals-In-Oakland.d9160.Car-Rental-Guide)[Oakland Vacation Packages](https://expedia.com/Oakland.d9160.Destination-Travel-Guides) ![Waterfall at Swallow Falls](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jenn Charbonneau ![](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=9160&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=9160&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=9160&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=9160&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oakland chalets ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/d6784fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/542780ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/a13f4c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120880000/120875900/120875821/0f9bd9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeview Chalet in Deep Creek Lake + Hot Tub [](https://www.expedia.com/Oakland-Hotels-Lakeview-Chalet-In-Deep-Creek-Lake-Hot-Tub.h120875821.Hotel-Information) Oakland $798 nightly $846 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Oakland-Hotels-Lakeview-Chalet-In-Deep-Creek-Lake-Hot-Tub.h120875821.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/0bf4912f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/f867aaa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/dbf25a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/81a9de4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wooded Retreat w Hot Tub, Loft, Game Room & Sauna [](https://www.expedia.com/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.Hotel-Information) Oakland 10/10 Exceptional (1 review) "Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bonny S. $608 nightly $669 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/8496eca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/267d9fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/a6a774c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117940000/117931100/117931073/fe0daeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits [](https://www.expedia.com/Davis-Hotels-Step-Inside-The-Yellow-Door-Your-Mountain-Chalet-Escape-Awaits.h117931073.Hotel-Information) Davis $397 nightly $450 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Davis-Hotels-Step-Inside-The-Yellow-Door-Your-Mountain-Chalet-Escape-Awaits.h117931073.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.com/Hotel-Search?startDate=2026-03-26&endDate=2026-03-27®ionId=9160&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_9160) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=COTTAGE) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=APART_HOTEL) Condos [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=CHALET) Apartments [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-06-10&d1=2026-06-10&endDate=2026-06-13&d2=2026-06-13&lodging=VILLA) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Chalets.d9160-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOakland-Chalets.d9160-aaChalets.Travel-Guide-Accommodation) ## Top Oakland Hotel Reviews ![The Garrett Inn](https://images.trvl-media.com/lodging/15000000/14920000/14910400/14910340/d2b2d172_y.jpg) ### The Garrett Inn 10/10 Excellent "Convenient parking. Clean room. Air conditioning just right. Convenient to stores and restaurants. Have stayed here twice now and when in the area, would stay again." [](https://expedia.com/Cumberland-Hotels-The-Garrett-Inn.h14910340.Hotel-Information) ![Baja Motel](https://images.trvl-media.com/lodging/100000000/99840000/99839500/99839480/9095b56d_y.jpg) ### Baja Motel 10/10 Excellent "The room was clean and the king bed was quite comfortable. The heater was a bit loud but very effective, and the heated air fan in the bath was a nice touch; plenty of hot water, too. The microwave oven was small but worked well, and the mini-fridge was bigger than many we've seen. The staff were friendly and helpful, and cheerfully accomodated our late arrival. " [](https://expedia.com/Oakland-Hotels-Riverside-Suites.h99839480.Hotel-Information) ![Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit](https://images.trvl-media.com/lodging/96000000/95210000/95208700/95208667/6841633a_y.jpg) ### Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit 10/10 Excellent "We had a wonderful time! The house was perfect with so many extras to make our stay comfortable, thank you! " [](https://expedia.com/Oakland-Hotels-Lakefront.h95208667.Hotel-Information) ![In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,](https://images.trvl-media.com/lodging/90000000/89150000/89146100/89146013/w944h527x0y0-6b6f8ac0_y.jpg) ### In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp, 10/10 Excellent "Everything was great " [](https://expedia.com/Oakland-Hotels-In-The-Heart-Of-Deep-Creek.h89146013.Hotel-Information) ![Lakefront/Dock/Amazing views HotTub](https://images.trvl-media.com/lodging/78000000/77820000/77813400/77813386/c4e314c7_y.jpg) ### Lakefront/Dock/Amazing views HotTub 10/10 Excellent "We had an absolute wonderful stay at Hygge Memories. The house was beautiful and spotless, and had everything we needed for a comfortable getaway! The lake front view was stunning - the perfect backdrop for relaxing and making memories! The location was ideal-close to everything, yet peaceful and private. The owners were fantastic to work with, friendly, responsive and truly made us feel welcomed! We would definitely stay here again and highly recommend this property to anyone looking for a great getaway!" [](https://expedia.com/Oakland-Hotels-8min2WISPLakefrontDockHotTub.h77813386.Hotel-Information) ![ Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek](https://images.trvl-media.com/lodging/25000000/24300000/24292000/24291953/10678050_y.jpg) ### Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek 10/10 Excellent "We had a wonderful stay this weekend at this adorable and well-appointed cabin! It had incredible amenities to make a family of 5 very comfortable in between skiing, snow-tubing and hiking. We enjoyed the scenery in the woods with the fire pit and lighting. Will definitely be back! " [](https://expedia.com/Cumberland-Hotels-Charming.h24291953.Hotel-Information) ![The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek](https://images.trvl-media.com/lodging/106000000/105960000/105953100/105953075/95bef466_y.jpg) ### The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek 10/10 Excellent "The location was great for our weekend getaway. Close to restaurants and shopping." [](https://expedia.com/Oakland-Hotels-The-Tiny-House-Deep-Creek-Lake-Centrally-Located-To-Everything-Deep-Creek.h105953075.Hotel-Information) ![The winter is coming !!!](https://images.trvl-media.com/lodging/23000000/22630000/22624200/22624198/1bd56ed5_y.jpg) ### The winter is coming !!! 10/10 Excellent "We had a fantastic stay at Winter is Coming!! The cabin was very warm and inviting. Chris was prompt in responding to any questions. It was exactly as described in the description and more! We would definitely recommend Chris and this cabin to others! So much fun. Hot tub was fantastic also!! " [](https://expedia.com/Cumberland-Hotels-Winter-Is-Coming.h22624198.Hotel-Information) ![Mt. Dew- AMAZING LAKE FRONT! 7 BR Home with Hot Tub, Fire Pit, Dock, Pool Table](https://images.trvl-media.com/lodging/35000000/34160000/34151200/34151122/381c360b_y.jpg) ### Mt. Dew- AMAZING LAKE FRONT! 7 BR Home with Hot Tub, Fire Pit, Dock, Pool Table 8/10 Good "Good communications. Home was clean and welcoming. " [](https://expedia.com/Oakland-Hotels-Stunning-7-Bedroom-65-Bath-Lakefront-Home-With-Dock-Slip.h34151122.Hotel-Information) ## Find out more about Oakland ## Oakland Chalets information | Number of reviews | 1 | | ----------------- | ---------- | | Accommodation | 10 Chalets | | Lowest Price | $450 | | Highest Price | $669 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Cabin Rentals in Garrett County ](https://www.expedia.com/Garrett-County-Cabins.d3000405803-aaCabins.Travel-Guide-Accommodation) - [Motels in Garrett County ](https://www.expedia.com/Garrett-County-Motels.d3000405803-aaMotels.Travel-Guide-Accommodation) - [Condo Rentals in Garrett County ](https://www.expedia.com/Garrett-County-Condos.d3000405803-aaCondos.Travel-Guide-Accommodation) - [Vacation Homes in Garrett County ](https://www.expedia.com/Garrett-County-Private-Vacation-Homes.d3000405803-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Garrett County Hotels ](https://www.expedia.com/Destinations-In-Garrett-County.d3000405803.Hotel-Destinations) - 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