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) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KM Moore # 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 [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-18&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland 4 Star Hotels ![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 Oakland 8.0/10 Very good (2) "Pasamos un buen tiempo en familia lo recomiendo es un buen lugar para visitar " ![](https://a.travel-assets.com/egds/marks/flags/mx.svg) Cesar [](https://www.expedia.ca/Oakland-Hotels-Loft-Of-Luxury.h77817107.Hotel-Information) ![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/fc755c7a.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 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/b0b25d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011499/0022bfa7.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) ### Strawberry Fields 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/76000000/75980000/75971000/75970958/77d64256.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/76000000/75980000/75971000/75970958/59abb181.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) ### Bears Lair 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!" ![](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/f9df32bf.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) ### Acorn Cottage Oakland [](https://www.expedia.ca/Oakland-Hotels-Acorn-Cottage.h105788974.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/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) ![House (4 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/94000000/93540000/93536000/93535942/b6007274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Freedom Mountainside [](https://www.expedia.ca/Oakland-Hotels-Mountain-Freedom.h93535942.Hotel-Information) ![House (4 Bedrooms) | Property amenity](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/97000000/96180000/96178700/96178654/4d7adca8.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/e914b2de.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/fb477d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Butterfly Retreat 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 Oakland [](https://www.expedia.ca/Oakland-Hotels-Bee-Tree-II.h87715789.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/c47eb636.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) ### Home Sweet Cabin 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/77000000/76020000/76011900/76011869/0725e6b7.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/77000000/76020000/76011900/76011869/2c1805b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windsor House Oakland [](https://www.expedia.ca/Oakland-Hotels-Windsor-House.h76011869.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/96000000/95450000/95445800/95445799/458a68b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Beautiful View 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." ![](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/f6e08481.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76010300/76010256/667e8680.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/d2dfad2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76010300/76010256/126da010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain House Oakland [](https://www.expedia.ca/Oakland-Hotels-Mountain-House.h76010256.Hotel-Information) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/639a4879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/7925b150.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/0465414a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/77000000/76010000/76009900/76009805/b18ef436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakestar Chalet 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. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela [](https://www.expedia.ca/Oakland-Hotels-Lakestar-Chalet.h76009805.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/dc749a97.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) ### St. Bart's Retreat Oakland [](https://www.expedia.ca/Oakland-Hotels-St-Barts-Retreat.h76011467.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) | Front of property](https://images.trvl-media.com/lodging/77000000/76020000/76011500/76011458/6e3e793c.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/f399fb38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Some Kind of Wonderful Silver Ridge [](https://www.expedia.ca/Oakland-Hotels-Some-Kind-Of-Wonderful.h76011458.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76020000/76010400/76010339/99aa3446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Jetted Tub | Private kitchen](https://images.trvl-media.com/lodging/77000000/76020000/76010400/76010339/86b05f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Jetted Tub | Living area](https://images.trvl-media.com/lodging/77000000/76020000/76010400/76010339/97ab170f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76020000/76010400/76010339/6d7d7dce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deja Blue Oakland 10/10 Exceptional (1) "Deja Blue was extremely clean and comfortable for my family get away. Provided all neede items. I will definitely use Taylor Made again" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Elgin [](https://www.expedia.ca/Oakland-Hotels-Paddles-And-Poles.h76010339.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/96000000/95450000/95446700/95446644/2f4fc117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Winter View Oakland 6.0/10 (2) "Great place for a weekend getaway!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea [](https://www.expedia.ca/Oakland-Hotels-A-Winter-View.h95446644.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/77000000/76020000/76011700/76011644/5df1b45f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Property amenity](https://images.trvl-media.com/lodging/77000000/76020000/76011700/76011644/7c8666a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Airy Oakland [](https://www.expedia.ca/Oakland-Hotels-The-Mountain-Airy.h76011644.Hotel-Information) ![House, Multiple Beds, Hot Tub | View from property](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011857/c095c765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011857/e504c353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011857/8a1827c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Hot Tub | Private kitchen](https://images.trvl-media.com/lodging/77000000/76020000/76011900/76011857/e977e3b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waves N' Moguls Oakland [](https://www.expedia.ca/Oakland-Hotels-Waves-N-Moguls.h76011857.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 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... ![](https://a.travel-assets.com/egds/marks/flags/us.svg) veronica [](https://www.expedia.ca/Oakland-Hotels-American-Pride.h75969905.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=31%2F10%2F2025&endDate=01%2F11%2F2025&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=18%2F10%2F2025&endDate=19%2F10%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=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025®ionId=9160&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=18%2F10%2F2025&endDate=19%2F10%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 Get away to upscale Oakland! Enjoy the lake views, skiing, and camping. [See all hotels in Oakland](https://www.expedia.ca/Hotel-Search?startDate=2025-10-31&endDate=2025-11-01&adults=2®ionId=9160) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=900&h=675&p=1&q=high) Photo by KM Moore ## 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? > To book a 4-star hotel in Oakland that fits your budget, make use of Expedia's filter tool. Check out the availability during your vacation dates and use our pricing filter to set your maximum rate. You can also list your results by the most budget-friendly escape first. > > > > - Search for the lowest price ### What's the difference between 5-star and 4-star hotels in Oakland? > Give yourself the luxury treatment during your Oakland getaway by choosing a 4-star hotel. As well as featuring upscale surroundings, these retreats are usually filled with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your stay an even more lavish and special one. 24-hour concierge assistance, on-site spas and gourmet dining are only the start of the exclusive conveniences and services you'll likely get access to. ### Does Oakland have any 4-star all-inclusive resorts? > Enjoy a relaxing vacation experience where everything is included in the upfront price by using our "All inclusive" filter. Sticking to your budget is a piece of cake when your room, food, activities and entertainment are already taken care of. After something a little different? 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