Title: Oakland Chalets from CA $578 | 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) ![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__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 In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 27 - Mar 29](https://www.expedia.ca/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 three months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-05-22&endDate=2026-05-24&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/116000000/115060000/115059200/115059189/149ddcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/9e2e051a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/5b6cf464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/80270f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wooded Retreat w Hot Tub, Loft, Game Room & Sauna [](https://www.expedia.ca/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. CA $420 CA $956 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/d68aefb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/aca96b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/b7ecb6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115190000/115182200/115182127/ebb4b1a9.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. [](https://www.expedia.ca/Oakland-Hotels-Lake-Views-HOT-TUB-Central-Location-Walk-To-Coffee.h115182127.Hotel-Information) Oakland 10/10 Exceptional (4 reviews) "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 $210 CA $578 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Oakland-Hotels-Lake-Views-HOT-TUB-Central-Location-Walk-To-Coffee.h115182127.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) ![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) ![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) ### Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits [](https://www.expedia.ca/Davis-Hotels-Step-Inside-The-Yellow-Door-Your-Mountain-Chalet-Escape-Awaits.h117931073.Hotel-Information) Davis CA $311 CA $681 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-02-09&endDate=2026-02-10®ionId=9160&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=APARTMENT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Maryland%2C+United+States+of+America®ionId=9160&latLong=39.407875%2C-79.406715&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&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.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 ![Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing ](https://images.trvl-media.com/lodging/64000000/63750000/63746800/63746763/78c8b009_y.jpg) ### Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing 10/10 Excellent "The house was awesome! It was beautifully decorated with amazing views of the lake. We had a great time. " [](https://expedia.ca/Oakland-Hotels-Lakefront.h63746763.Hotel-Information) ![The Garrett Inn](https://images.trvl-media.com/lodging/15000000/14920000/14910400/14910340/d2b2d172_y.jpg) ### The Garrett Inn 10/10 Excellent "Very kind staff, overall pleasant experience " [](https://expedia.ca/Cumberland-Hotels-The-Garrett-Inn.h14910340.Hotel-Information) ![Level lakefront, family-friendly, hot tub, low fees, private dock](https://images.trvl-media.com/lodging/55000000/54920000/54911400/54911380/f7244719_y.jpg) ### Level lakefront, family-friendly, hot tub, low fees, private dock 10/10 Excellent "Cozy comfortable & clean house , super convenient to Wisp, yet private and quiet. " [](https://expedia.ca/Cumberland-Hotels-Level-Lakefront.h54911380.Hotel-Information) ![Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip](https://images.trvl-media.com/lodging/96000000/95210000/95208700/95208674/7af77293_y.jpg) ### Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip 10/10 Excellent "This location was a great way for us to experience Deep Creek Lake in the winter months. The house was spacious, well-stocked, and spotless on arrival. We had a wonderful weekend and will look forward to coming back in the future!" [](https://expedia.ca/Oakland-Hotels-Lakefront.h95208674.Hotel-Information) ![The Lake House- 5 bedroom in quiet area with hot tub and pool table](https://images.trvl-media.com/lodging/121000000/120050000/120048200/120048180/18d2a03b_y.jpg) ### The Lake House- 5 bedroom in quiet area with hot tub and pool table 8/10 Good "Beautiful house, plenty of room, " [](https://expedia.ca/Oakland-Hotels-The-Lake-House-5-Bedroom-In-Quiet-Area-With-Hot-Tub-And-Pool-Table.h120048180.Hotel-Information) ![Cabin in the Woods](https://images.trvl-media.com/lodging/93000000/92100000/92092300/92092234/f8871107_y.jpg) ### Cabin in the Woods 10/10 Excellent "So many little details that were so well thought out , made this experience at your property amazing. Our 9 year old and 18 year old didnt complain once the whole 3 days we were there. Hot tub was amazing, game area was great. We enjoyed the board games and puzzles. Bedrooms were clean and comfy. Access to extra blankets was great too because it was so cold that weekend. We enjoyed every part of our stay and enjoyed just being together and were thankful your place could accommodate that. Thanks for driving so far to fix the frozen pipes that busted so we could still come. Great owners and great communication ! Definitely recommend this property " [](https://expedia.ca/Oakland-Hotels-Cabin-In-The-Woods.h92092234.Hotel-Information) ![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) ### Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp 10/10 Excellent "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. The house is very pet friendly, has all the room we need and is in a perfect location for everything Deep Creek has to offer. Our first stay was during the summer and the dock was our reason for renting. We will definitely rent again. " [](https://expedia.ca/Oakland-Hotels-Bon-Vivant-Pet-Friendly.h104788464.Hotel-Information) ![The winter is coming !!!](https://images.trvl-media.com/lodging/23000000/22630000/22624200/22624198/d1f7f369_y.jpg) ### The winter is coming !!! 10/10 Excellent "Great place to stay for our family New Years get-away. Only issues encountered was the quantity of silverware did not match the stay capacity and we did not have a snow shovel (it snowed every day we were there which was great for the stay)." [](https://expedia.ca/Cumberland-Hotels-Winter-Is-Coming.h22624198.Hotel-Information) ![Baja Motel](https://images.trvl-media.com/lodging/100000000/99840000/99839500/99839480/34bea603_y.jpg) ### Baja Motel 10/10 Excellent "Everything is great " [](https://expedia.ca/Oakland-Hotels-Riverside-Suites.h99839480.Hotel-Information) ## Find out more about Oakland ## Oakland Chalets information | Number of reviews | 5 | | ----------------- | ---------- | | Accommodation | 10 Chalets | | Lowest Price | CA $578 | | Highest Price | CA $956 | ## 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) - 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