Title: 4 Stars Hotels in Oakland, Maryland - Find Cheap Oakland Hotels With 4 Stars | Expedia.ca [Oakland Travel Guide](https://expedia.ca/Oakland.dx9160)[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)[Flights to Oakland](https://expedia.ca/Cheap-Flights-To-Oakland.d9160.Travel-Guide-Flights)[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 # 4 Stars Hotels in Oakland, Maryland - ![](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 4 Star Hotels Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-12-26&endDate=2025-12-27&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-12-27&endDate=2025-12-28&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-01-02&endDate=2026-01-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oakland 4-star hotels ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/a709d25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/f48c82cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/b4092160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/13e1eb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bear Hollow Lodge by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Bear-Hollow-Lodge.h75970245.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-Bear-Hollow-Lodge.h75970245.Hotel-Information) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011499/72883e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011499/w2420h1814x0y1-9f219a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011499/b0b25d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011499/99b1412e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Strawberry Fields by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Strawberry-Fields.h76011499.Hotel-Information) Oakland 10/10 Exceptional (1) [](https://www.expedia.ca/Oakland-Hotels-Strawberry-Fields.h76011499.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75971000/75970958/8d4cf6f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75971000/75970958/49d1e427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75971000/75970958/77d64256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75971000/75970958/679eb559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bears Lair by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Bears-Lair.h75970958.Hotel-Information) Oakland 10/10 Exceptional (1) "The property was more than expected and we had a wonderful time. Everything we wanted to do was within driving distance. Wonderful experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane [](https://www.expedia.ca/Oakland-Hotels-Bears-Lair.h75970958.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/106000000/105790000/105789000/105788974/3960dd0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/106000000/105790000/105789000/105788974/00824e7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/106000000/105790000/105789000/105788974/6c4a4491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/106000000/105790000/105789000/105788974/7bd893a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Acorn Cottage by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Acorn-Cottage.h105788974.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-Acorn-Cottage.h105788974.Hotel-Information) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/78000000/77820000/77817200/77817107/91474100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/78000000/77820000/77817200/77817107/2bb9d907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/78000000/77820000/77817200/77817107/4548af91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/78000000/77820000/77817200/77817107/126580b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loft of Luxury by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Loft-Of-Luxury.h77817107.Hotel-Information) Oakland 8.0/10 Very good (2) "Pasamos un buen tiempo en familia lo recomiendo es un buen lugar para visitar " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Cesar [](https://www.expedia.ca/Oakland-Hotels-Loft-Of-Luxury.h77817107.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/97000000/96180000/96178700/96178654/9ac592e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/97000000/96180000/96178700/96178654/51f9c71b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/97000000/96180000/96178700/96178654/11bf3bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/97000000/96180000/96178700/96178654/4e609e64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Butterfly Retreat by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Butterfly-Retreat.h96178654.Hotel-Information) Mountainside [](https://www.expedia.ca/Oakland-Hotels-Butterfly-Retreat.h96178654.Hotel-Information) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/88000000/87720000/87715800/87715789/ad7b6132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/88000000/87720000/87715800/87715789/3e8ada34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/88000000/87720000/87715800/87715789/3352e909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/88000000/87720000/87715800/87715789/e5207246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bee Tree II by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Bee-Tree-II.h87715789.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-Bee-Tree-II.h87715789.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/94000000/93540000/93536000/93535942/2fae40b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/94000000/93540000/93536000/93535942/1fe5828b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/94000000/93540000/93536000/93535942/b66c5589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/94000000/93540000/93536000/93535942/ba36cc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Freedom by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Mountain-Freedom.h93535942.Hotel-Information) Mountainside [](https://www.expedia.ca/Oakland-Hotels-Mountain-Freedom.h93535942.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009500/76009491/bc4acf17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009500/76009491/2a9f3f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009500/76009491/e5fd70f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009500/76009491/c47eb636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home Sweet Cabin by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Home-Sweet-Cabin.h76009491.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-Home-Sweet-Cabin.h76009491.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011869/9ff4801f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011869/2c1805b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011869/3e27cd59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011869/cb05c32f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windsor House by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Windsor-House.h76011869.Hotel-Information) Paradise Point [](https://www.expedia.ca/Oakland-Hotels-Windsor-House.h76011869.Hotel-Information) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/9e6556dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/0dd61ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/bc1431ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/2eab723c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakestar Chalet by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Lakestar-Chalet.h76009805.Hotel-Information) Oakland 8.0/10 Very good (1) "Property matched description. It could’ve been a bit cleaner on arrival. The tvs did not work, but everything else was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela [](https://www.expedia.ca/Oakland-Hotels-Lakestar-Chalet.h76009805.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445799/9a64c81c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445799/857e1411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445799/b3e6dd30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/96000000/95450000/95445800/95445799/b95badbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Beautiful View by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-A-Beautiful-View.h95445799.Hotel-Information) Oakland 8.0/10 Very good (2) "Cute place with updated furnishings and appliances, right across the street from Deep Creek Lake boat rentals, jet skis, restaurants and Lakeside Creamery. 15 minute drive to Swallow Falls and quick drive to any other activity offered." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie [](https://www.expedia.ca/Oakland-Hotels-A-Beautiful-View.h95445799.Hotel-Information) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76010300/76010256/c4571083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/77000000/76020000/76010300/76010256/1350d72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76010300/76010256/e969ed7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76010300/76010256/e8fbb03f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain House by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Mountain-House.h76010256.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-Mountain-House.h76010256.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011458/fef1f61b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011458/d15b08f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011458/012b16c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011458/f399fb38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Some Kind of Wonderful by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Some-Kind-Of-Wonderful.h76011458.Hotel-Information) Silver Ridge [](https://www.expedia.ca/Oakland-Hotels-Some-Kind-Of-Wonderful.h76011458.Hotel-Information) ![House (Multiple Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011467/a069023b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011467/77f23f4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011467/37fb3fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (Multiple Bedrooms) | Front of property](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011467/b30bd043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St. Bart's Retreat by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-St-Barts-Retreat.h76011467.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-St-Barts-Retreat.h76011467.Hotel-Information) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011700/76011644/c2e6150f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011700/76011644/f89d868f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011700/76011644/47686216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011700/76011644/5df1b45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Airy by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-The-Mountain-Airy.h76011644.Hotel-Information) Oakland 10/10 Exceptional (1) "The whole house was beautiful and clean we loved our stay the hot tub was lovely and the chimney made it very cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yesenia [](https://www.expedia.ca/Oakland-Hotels-The-Mountain-Airy.h76011644.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/96000000/95450000/95446700/95446644/972a4ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/96000000/95450000/95446700/95446644/f8660f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/96000000/95450000/95446700/95446644/71b344e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/96000000/95450000/95446700/95446644/680f6aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Winter View by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-A-Winter-View.h95446644.Hotel-Information) Oakland 6.0/10 (2) "Great place for a weekend getaway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea [](https://www.expedia.ca/Oakland-Hotels-A-Winter-View.h95446644.Hotel-Information) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75970000/75970000/75969905/695d6476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75970000/75970000/75969905/d87d101e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75970000/75970000/75969905/42419d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75970000/75970000/75969905/2652885d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### American Pride by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-American-Pride.h75969905.Hotel-Information) Blakeslee 6.0/10 (1) "This is a spacious home with plenty of space for a large family gathering and most importantly graciously allows dogs. Very close to the WISP resort, and minutes away from the lake. Owners have thoughtfully included plenty of "extras" to make guests feel at home like board games, DVDs, a game room, and a well-appointed kitchen! Home however is starting to show lots of wear and tear. To mention a few; a non-working gas fireplace (a pretty big deal for winter stays) missing door handles on the... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) veronica [](https://www.expedia.ca/Oakland-Hotels-American-Pride.h75969905.Hotel-Information) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011481/7a1a4c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011481/2c9bc605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011481/87289890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011481/90d808c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stargazer by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-Stargazer.h76011481.Hotel-Information) Oakland [](https://www.expedia.ca/Oakland-Hotels-Stargazer.h76011481.Hotel-Information) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/102000000/101150000/101141400/101141390/w2880h2158x0y1-9694f18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/102000000/101150000/101141400/101141390/6abfb946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/102000000/101150000/101141400/101141390/w2880h2158x0y1-6c9e4019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/102000000/101150000/101141400/101141390/w2880h2159x0y1-df55b05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bears Lodge by Taylor Made Deep Creek [](https://www.expedia.ca/Oakland-Hotels-3-Bears-Lodge.h101141390.Hotel-Information) Paradise Point [](https://www.expedia.ca/Oakland-Hotels-3-Bears-Lodge.h101141390.Hotel-Information) ![](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%2F4Star-Oakland-Hotels.s40-0-d9160.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Oakland-Hotels.s40-0-d9160.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Oakland. ![Preston on the Lake 5 Bedroom House](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/1a59f6a9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Preston on the Lake 5 Bedroom House 585 Glendale Road Oakland MD [Get rates](https://expedia.ca/Hotel-Search?startDate=09%2F01%2F2026&endDate=10%2F01%2F2026&selected=32721047&PinnedHotelID=32721047&HadPinnedHotel=true®ionId=9160) [](https://expedia.ca/Cumberland-Hotels-Preston-On-The-Lake-5-Bedroom-House.h32721047.Hotel-Information) Still don't see what you're looking for? [See all properties in Oakland.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=9160&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=9160&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=9160&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=9160&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=9160&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F12%2F2025&endDate=28%2F12%2F2025®ionId=9160&star=40&star=40&amenities=WATER_PARK) 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. ## Learn more about Oakland Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors. [See all hotels in Oakland](https://www.expedia.ca/Hotel-Search?startDate=2026-01-09&endDate=2026-01-10&adults=2®ionId=9160) ![Waterfall at Swallow Falls](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=576&h=768&p=1&q=high) Photo by Jenn Charbonneau ## Top Oakland Hotel Reviews ## Find out more about Oakland If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Oakland are calling your name. Known for providing first-rate service in amazing locations, each of the Oakland 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Oakland. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Oakland, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Oakland hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Oakland? > - Search for the lowest price ### What's the difference between 5-star and 4-star hotels in Oakland? ### Does Oakland have any 4-star all-inclusive resorts? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Sharpsburg ](https://www.expedia.ca/1Star-Sharpsburg-Hotels.s10-0-d157080.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Paradise Point ](https://www.expedia.ca/2Star-Paradise-Point-Oakland-Hotels.s20-n553248635976481309-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Downtown Frederick ](https://www.expedia.ca/3Star-Downtown-Frederick-Frederick-Hotels.s30-n553248635976468745-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Westernport ](https://www.expedia.ca/4Star-Westernport-Hotels.s40-0-d3000440935.Travel-Guide-Filter-Hotels) - 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