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491 Houses

    0

    Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes

    Garrett County / Oakland

    Oakland house

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Child Friendly
    • Car not necessary
    • Air conditioning

    Price per night from

    $133

    Responds fast!
    avg. 1 hour 31 minutes

    Price per night from

    $133

      0

      Lakefront cabin w/ private dock and great views - close to skiing!

      Garrett County / Oakland

      Oakland house

      4 10 min stay varies

      • 4 bedrooms
      • sleeps 10
      • min stay varies
      • Child Friendly
      • Car not necessary

      Price per night from

      $250

      Responds fast!
      avg. 1 hour 31 minutes

      Price per night from

      $250

        24

        The Haven - 8 Master Suites, Private Pool, - House

        Garrett County / Oakland

        Oakland house

        8 16 min stay varies

        • 8 bedrooms
        • sleeps 16
        • min stay varies
        • Child Friendly

        Price per night from

        $1,512

        Price per night from

        $1,512

          0

          NEW LISTING! Spacious home w/convenient location & hot tub, near lake & dining

          Garrett County / Oakland

          Oakland house

          4 10 min stay varies

          • 4 bedrooms
          • sleeps 10
          • min stay varies
          • Child Friendly
          • Car not necessary
          • Air conditioning

          Price per night from

          $179

          Responds fast!
          avg. 1 hour 9 minutes

          Price per night from

          $179

            0

            NEW LISTING! Charming cabin w/ lake access, dock, private hot tub, & fire pit

            Garrett County / Oakland

            Oakland house

            3 8 min stay varies

            • 3 bedrooms
            • sleeps 8
            • min stay varies
            • Child Friendly
            • Car not necessary

            Price per night from

            $107

            Responds fast!
            avg. 1 hour 37 minutes

            Price per night from

            $107

              0

              Tranquil home w/ private hot tub & game room - close to lake access

              Garrett County / Oakland

              Oakland house

              5 11 min stay varies

              • 5 bedrooms
              • sleeps 11
              • min stay varies
              • Child Friendly
              • Car not necessary
              • Air conditioning

              Price per night from

              $211

              Responds fast!
              avg. 1 hour 21 minutes

              Price per night from

              $211

                0

                Dog-friendly lakefront home w/ hot tub, dock, shared tennis - near the slopes!

                Garrett County / Oakland

                Oakland house

                3 10 min stay varies

                • 3 bedrooms
                • sleeps 10
                • min stay varies
                • Child Friendly
                • Car not necessary
                • Air conditioning

                Price per night from

                $184

                Responds fast!
                avg. 1 hour 31 minutes

                Price per night from

                $184

                  138

                  Spacious home on a lake w/ private hot tub & pool table - near the slopes!

                  Garrett County / Oakland

                  Oakland house

                  5 12 min stay varies

                  • 5 bedrooms
                  • sleeps 12
                  • min stay varies
                  • Child Friendly
                  • Car not necessary
                  • Air conditioning

                  Price per night from

                  $198

                  Responds fast!
                  avg. 1 hour 27 minutes

                  Price per night from

                  $198

                    0

                    Dog-friendly cabin in the woods with hot tub, furnished deck, & pool table

                    Garrett County / Oakland

                    Oakland house

                    3 10 min stay varies

                    • 3 bedrooms
                    • sleeps 10
                    • min stay varies
                    • Child Friendly
                    • Car not necessary
                    • Pet Friendly

                    Price per night from

                    $177

                    Responds fast!
                    avg. 1 hour 31 minutes

                    Price per night from

                    $177

                      0

                      Roomy, lakefront, dog-friendly home w/hot tub, game room, dock and more!

                      Garrett County / Oakland

                      Oakland house

                      6 25 min stay varies

                      • 6 bedrooms
                      • sleeps 25
                      • min stay varies
                      • Child Friendly
                      • Car not necessary
                      • Air conditioning

                      Price per night from

                      $330

                      Responds fast!
                      avg. 1 hour 37 minutes

                      Price per night from

                      $330

                        90

                        Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!

                        Garrett County / Oakland

                        Oakland house

                        3 6 min stay varies

                        • 3 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Child Friendly
                        • Car not necessary
                        • Pet Friendly

                        Price per night from

                        $111

                        Responds fast!
                        avg. 1 hour 31 minutes

                        Price per night from

                        $111

                        (12) Excellent 

                          31

                          Ski Solitude

                          Garrett County / Oakland

                          Oakland house

                          3 6 min stay varies

                          • 3 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Child Friendly
                          • Private garden

                          Price per night from

                          $114

                          Responds fast!
                          avg. 7 minutes

                          Price per night from

                          $114

                          (29) Excellent 

                            22

                            Red Run Cabin

                            Garrett County / Oakland

                            Oakland log cabin

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Child Friendly
                            • Air conditioning
                            • Pet Friendly
                            “Beautiful, clean home in a perfect setting!” My husband, two year old daughter, dog and I just returned from a five night stay at Red Run Cabin. The home, although nothing fancy, was beautiful and well kept. We generally always stay in cabins or cond
                            …see more

                            Price per night from

                            $162

                            Responds fast!
                            avg. 2 hours 2 minutes

                            Price per night from

                            $162

                              23

                              Preston on the Lake

                              Garrett County / Oakland

                              Oakland house

                              5 14 min stay varies

                              • 5 bedrooms
                              • sleeps 14
                              • min stay varies
                              • Child Friendly

                              Price per night from

                              $1,080

                              Price per night from

                              $1,080

                                0

                                Lake access chalet-style home w/ 2 furnished patios, & private hot tub - dogs OK

                                Garrett County / Oakland

                                Oakland house

                                4 12 min stay varies

                                • 4 bedrooms
                                • sleeps 12
                                • min stay varies
                                • Child Friendly
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $179

                                Responds fast!
                                avg. 1 hour 37 minutes

                                Price per night from

                                $179

                                  0

                                  NEW LISTING! Dog-friendly family cabin with private hot tub & dock access

                                  Garrett County / Oakland

                                  Oakland house

                                  3 8 min stay varies

                                  • 3 bedrooms
                                  • sleeps 8
                                  • min stay varies
                                  • Child Friendly
                                  • Car not necessary
                                  • Pet Friendly

                                  Price per night from

                                  $187

                                  Responds fast!
                                  avg. 1 hour 9 minutes

                                  Price per night from

                                  $187

                                    23

                                    Innisfree - Spacious Chalet with Sunset La

                                    Garrett County / Oakland

                                    Oakland house

                                    5 16 min stay varies

                                    • 5 bedrooms
                                    • sleeps 16
                                    • min stay varies
                                    • Child Friendly

                                    Price per night from

                                    $378

                                    Price per night from

                                    $378

                                      17

                                      Winter is Coming

                                      Garrett County / Oakland

                                      Oakland house

                                      3 8 min stay varies

                                      • 3 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • Child Friendly

                                      Price per night from

                                      $343

                                      Responds fast!
                                      avg. 9 minutes

                                      Price per night from

                                      $343

                                        24

                                        Windsor House

                                        Garrett County / Oakland

                                        Oakland house

                                        4 12 min stay varies

                                        • 4 bedrooms
                                        • sleeps 12
                                        • min stay varies
                                        • Child Friendly

                                        Price per night from

                                        $248

                                        Price per night from

                                        $248

                                        (1)  

                                          0

                                          Dog-friendly, lakefront log home on a quiet cove - front deck & shared dock

                                          Garrett County / Oakland

                                          Oakland house

                                          3 10 min stay varies

                                          • 3 bedrooms
                                          • sleeps 10
                                          • min stay varies
                                          • Child Friendly
                                          • Car not necessary
                                          • Pet Friendly

                                          Price per night from

                                          $138

                                          Responds fast!
                                          avg. 1 hour 37 minutes

                                          Price per night from

                                          $138

                                            24

                                            The Mountain Airy

                                            Garrett County / Oakland

                                            Oakland house

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Child Friendly

                                            Price per night from

                                            $184

                                            Price per night from

                                            $184

                                              29

                                              Charming lake house w/ private hot tub & great views from the deck - dogs OK!

                                              Garrett County / Oakland

                                              Oakland house

                                              4 10 min stay varies

                                              • 4 bedrooms
                                              • sleeps 10
                                              • min stay varies
                                              • Child Friendly
                                              • Car not necessary
                                              • Air conditioning

                                              Price per night from

                                              $168

                                              Responds fast!
                                              avg. 1 hour 27 minutes

                                              Price per night from

                                              $168

                                                24

                                                Lake House

                                                Garrett County / Oakland

                                                Oakland house

                                                4 12 min stay varies

                                                • 4 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Child Friendly

                                                Price per night from

                                                $189

                                                Price per night from

                                                $189

                                                  17

                                                  El Dorado - Beautiful 4 Bedroom Lakefront

                                                  Garrett County / Oakland

                                                  Oakland house

                                                  4 8 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Child Friendly

                                                  Price per night from

                                                  $315

                                                  Price per night from

                                                  $315

                                                    24

                                                    The Quarterdeck

                                                    Garrett County / Oakland

                                                    Oakland house

                                                    4 12 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 12
                                                    • min stay varies
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $265

                                                    Price per night from

                                                    $265

                                                      24

                                                      Duffy's Oar House

                                                      Garrett County / Oakland

                                                      Oakland house

                                                      5 10 min stay varies

                                                      • 5 bedrooms
                                                      • sleeps 10
                                                      • min stay varies
                                                      • Child Friendly

                                                      Price per night from

                                                      $252

                                                      Price per night from

                                                      $252

                                                        24

                                                        Hideaway - Picturesque 2 Bedroom Cottage

                                                        Garrett County / Oakland

                                                        Oakland house

                                                        2 8 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 8
                                                        • min stay varies
                                                        • Child Friendly

                                                        Price per night from

                                                        $145

                                                        Price per night from

                                                        $145

                                                          24

                                                          Sunrise - Remarkable 4 bedroom lakefront

                                                          Garrett County / Oakland

                                                          Oakland house

                                                          4 9 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 9
                                                          • min stay varies
                                                          • Child Friendly

                                                          Price per night from

                                                          $220

                                                          Price per night from

                                                          $220

                                                            23

                                                            Stargazer - Spacious 4 bedroom home with p

                                                            Garrett County / Oakland

                                                            Oakland house

                                                            4 10 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Child Friendly

                                                            Price per night from

                                                            $378

                                                            Price per night from

                                                            $378

                                                              24

                                                              Changes in Attitude

                                                              Garrett County / Oakland

                                                              Oakland house

                                                              5 14 min stay varies

                                                              • 5 bedrooms
                                                              • sleeps 14
                                                              • min stay varies
                                                              • Child Friendly

                                                              Price per night from

                                                              $461

                                                              Price per night from

                                                              $461

                                                                24

                                                                San-Stress

                                                                Garrett County / Oakland

                                                                Oakland house

                                                                4 10 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • min stay varies
                                                                • Child Friendly

                                                                Price per night from

                                                                $216

                                                                Price per night from

                                                                $216

                                                                  24

                                                                  Finn McCool's

                                                                  Garrett County / Oakland

                                                                  Oakland house

                                                                  5 14 min stay varies

                                                                  • 5 bedrooms
                                                                  • sleeps 14
                                                                  • min stay varies
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $378

                                                                  Price per night from

                                                                  $378

                                                                    24

                                                                    Cross the River

                                                                    Garrett County / Oakland

                                                                    Oakland house

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $126

                                                                    Price per night from

                                                                    $126

                                                                      23

                                                                      Mountain House

                                                                      Garrett County / Oakland

                                                                      Oakland house

                                                                      5 14 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 14
                                                                      • min stay varies
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $220

                                                                      Price per night from

                                                                      $220

                                                                        18

                                                                        Hidden Treasure

                                                                        Garrett County / Oakland

                                                                        Oakland house

                                                                        4 8 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $133

                                                                        Price per night from

                                                                        $133

                                                                          24

                                                                          Sunset Delight

                                                                          Garrett County / Oakland

                                                                          Oakland house

                                                                          9 24 min stay varies

                                                                          • 9 bedrooms
                                                                          • sleeps 24
                                                                          • min stay varies
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $1,134

                                                                          Price per night from

                                                                          $1,134

                                                                            24

                                                                            Hemlock Hideaway

                                                                            Garrett County / Oakland

                                                                            Oakland house

                                                                            6 16 min stay varies

                                                                            • 6 bedrooms
                                                                            • sleeps 16
                                                                            • min stay varies
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $397

                                                                            Price per night from

                                                                            $397

                                                                              24

                                                                              Lazy Days - Charming and charismatic 3 bed

                                                                              Garrett County / Oakland

                                                                              Oakland house

                                                                              3 10 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $284

                                                                              Price per night from

                                                                              $284

                                                                              About Oakland

                                                                              Located in the beautiful mountains of western Maryland, Oakland is the perfect woodland escape. Be the first to see the sun hit the green hills from your vacation home's bedroom balcony, then walk just minutes to Deep Creek Lake, perfect for boating, tubing, hiking, and swimming. Feel free to bring the water skis and kayak as there is plenty of space inside your vacation rental to store your equipment. While you are here, spend a day at Swallow Falls State Park, home to some of Maryland's most beautiful natural scenery. Hike along trails with panoramic views of rocky gorges, flowing rapids, and Muddy Creek Falls, a thrashing 53-foot waterfall. The park offers a large picnic area with a pavilion and playground, as well as nature programs, boat rentals, and a beach for swimming during the summer.

                                                                              Here are a few additional suggestions of things to do in the area:

                                                                              • Visit Maryland's Historic B&O Train Station: This authentic 1884 train station has been restored to its original Queen Anne condition. The train speaks to Oakland's old, small town feel and adjoins a shop that sells baked goods, candles and maple syrup.
                                                                              • See a show at Our Town Theatre: This little production company offers great local and imported talent. Be sure to check the current schedule while visiting, and catch great comedies, dramas, and more.
                                                                              • Visit the county's Historical Society Museum: Like the train station, the historical museum is a great place to learn about the area's history and get a feel for small town life in another era.
                                                                              • Play golf: Champion caliber Deep Creek golf courses offer some of the best greens in the state. After a day of golf, spend an afternoon indulging in a pedicure at a luxury Deep Creek spa.
                                                                              • Go horseback riding: Several private stables in the state park area offer one-on-one lessons or trail rides with a friendly knowledgeable guide.
                                                                              • Experience Deep Creek skiing: In the winter, Deep Creek offers pristine, powdery trails perfect for both cross country and downhill skiing.

                                                                              Experience the best of Oakland and the Deep Creek Lake area by staying in your own private luxury vacation rental. A trendy winter condo or summer apartment rental may be perfect for a long weekend getaway with friends. You may also decide to host your family and friends for a barbeque at your lakeside vacation home or mountain cabin. While you're visiting Oakland, make the most of your stay by scheduling a visit to nearby Swanton or McHenry.