Title: The Best Westernport, MD Chalets from $666 | Expedia.com [Westernport Travel Guide](https://expedia.com/Westernport.dx3000440935)[Hotels in Westernport](https://expedia.com/Westernport-Hotels.d3000440935.Travel-Guide-Hotels)[Vacation Rentals in Westernport](https://expedia.com/Westernport-Vacation-Rentals.d3000440935.Travel-Guide-VacationRentals)[Car Rentals in Westernport](https://expedia.com/Car-Rentals-In-Westernport.d3000440935.Car-Rental-Guide)[Westernport Vacation Packages](https://expedia.com/Westernport.d3000440935.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=3000440935&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=3000440935&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=3000440935&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=3000440935&startDate=2026-07-10&endDate=2026-07-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Westernport chalets ![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/dbf25a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115060000/115059200/115059189/d26529c9.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. $605 nightly $666 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Oakland-Hotels-Wooded-Retreat-W-Hot-Tub.h115059189.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=2026-03-31&endDate=2026-04-01®ionId=3000440935&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.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=APART_HOTEL) Condos [](https://www.expedia.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Westernport%2C+Maryland%2C+United+States+of+America®ionId=3000440935&latLong=39.485371%2C-79.044754&adults=2&startDate=2026-06-14&d1=2026-06-14&endDate=2026-06-17&d2=2026-06-17&lodging=CHALET) ![](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%2FWesternport-Chalets.d3000440935-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWesternport-Chalets.d3000440935-aaChalets.Travel-Guide-Accommodation) ## Top Westernport Hotel Reviews ![Ramada by Wyndham Cumberland Downtown](https://images.trvl-media.com/lodging/1000000/10000/7000/6988/8789b329_y.jpg) ### Ramada by Wyndham Cumberland Downtown 10/10 Excellent "Cumberland Ramada has met my hotel needs well. Over the last two winters I have commuted to Cumberland for weekday work. Last winter I stayed in multiple area hotels, but this winter settled on repeated stays at Ramada Downtown almost exclusively. The place is not fancy. But the rooms are clean, of ample size, with comfortable beds. Meanwhile, the price fits my reimbursement budget. I always request a town side room to get less train noise. Cumberland downtown shops and restaurants are readily accessible a block away on the revitalized Baltimore street. There is not too much to do in Cumberland, but at the Ramada you are close to what there is to do. Staff are friendly and helpful. The hotel location is five minutes from my work, so the convenience recommends it as well. " [](https://expedia.com/Cumberland-Hotels-Ramada-By-Wyndham-Cumberland-Downtown.h6988.Hotel-Information) ![Hampton Inn Frostburg](https://images.trvl-media.com/lodging/1000000/120000/119300/119265/ec1bb246_y.jpg) ### Hampton Inn Frostburg 10/10 Excellent "Very friendly staff and excellent facilities." [](https://expedia.com/Cumberland-Hotels-Hampton-Inn-Frostburg.h119265.Hotel-Information) ![Best Western Braddock Inn](https://images.trvl-media.com/lodging/1000000/30000/20300/20208/2dcd613c_y.jpg) ### Best Western Braddock Inn 8/10 Good "Pool area great, staff great, some of carpets worn and dirty. Mattress also worn but would stay again " [](https://expedia.com/Cumberland-Hotels-Best-Western-Braddock-Inn.h20208.Hotel-Information) ![Hampton Inn Cumberland](https://images.trvl-media.com/lodging/23000000/22790000/22789200/22789141/24ab5e40_y.jpg) ### Hampton Inn Cumberland 10/10 Excellent "The Hotel lobby, rooms…all very clean. Once you enter hotel lobby, it smells clean and fresh. Rooms were super clean, beds were comfortable, and room had upgraded amenities. Breakfast bar was great with all sorts food to choose from. It was a very pleasant stay." [](https://expedia.com/Cumberland-Hotels-Hampton-Inn-Cumberland.h22789141.Hotel-Information) ![Fairfield Inn & Suites by Marriott Cumberland](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758850/b025ee25_y.jpg) ### Fairfield Inn & Suites by Marriott Cumberland 8/10 Good "Location next to C&O and GAP trails with bike facilities for the riders. " [](https://expedia.com/Cumberland-Hotels-Fairfield-Inn-Suites-By-Marriott-Cumberland.h2758850.Hotel-Information) ![Lakefront Romantic Cabin Getaway:Hot Tub,Kayaks,Dock,Garden-OWLS NEST,DEEP CREEK](https://images.trvl-media.com/lodging/34000000/33950000/33948700/33948604/12585191_y.jpg) ### Lakefront Romantic Cabin Getaway:Hot Tub,Kayaks,Dock,Garden-OWLS NEST,DEEP CREEK 10/10 Excellent "Small cozy cabin with a beautiful view." [](https://expedia.com/Cumberland-Hotels-Owls-Nest.h33948604.Hotel-Information) ![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) ![Sleep Inn & Suites Cumberland - LaVale](https://images.trvl-media.com/lodging/16000000/15690000/15687200/15687145/fd5b4689_y.jpg) ### Sleep Inn & Suites Cumberland - LaVale 10/10 Excellent "Staff was nice. Breakfast was good. Pool clean annd warmed." [](https://expedia.com/Cumberland-Hotels-Sleep-Inn-Suites-Cumberland-LaVale.h15687145.Hotel-Information) ![LakeFront Lodge](https://images.trvl-media.com/lodging/121000000/120440000/120435200/120435187/cf5ded6c_y.jpg) ### LakeFront Lodge 10/10 Excellent "Very clean, view of ski area was great!" [](https://expedia.com/McHenry-Hotels-LakeFront-Lodge.h120435187.Hotel-Information) ## Find out more about Westernport ## Westernport Chalets information | Number of reviews | 1 | | ----------------- | ---------- | | Accommodation | 24 Chalets | | Lowest Price | $666 | | Highest Price | $666 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Cabin Rentals in Luke ](https://www.expedia.com/Luke-Cabins.d55806-aaCabins.Travel-Guide-Accommodation) - [B&B in Luke ](https://www.expedia.com/Luke-Bed-And-Breakfast.d55806-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luke Hotels ](https://www.expedia.com/Luke-Hotels.d55806.Travel-Guide-Hotels) - [5 Star Hotels in Luke ](https://www.expedia.com/5Star-Luke-Hotels.s50-0-d55806.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Barton ](https://www.expedia.com/Barton-Cabins.d553248626204850781-aaCabins.Travel-Guide-Accommodation) - [Barton Hotels ](https://www.expedia.com/Barton-Hotels.d553248626204850781.Travel-Guide-Hotels) - 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