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Oakland

Found in a region where you can find some pretty landscapes, Oakland is a great place to explore Western Maryland.

Packages in Oakland

Book a accommodation and flight package with Expedia and earn some savings. We love to minimize your worries by pairing up your lodging and flight bookings for even more great savings. There is a lot your family can do in Oakland with your extra cash.

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For Oakland, Cumberland, you will have a difficult time finding anything better for your budget than the prices at Expedia.

You can delay your travel reservations with us because we do not charge cancellation fees for almost all of our hotel reservations.

Oakland Vacation Packages

From Oakland, Pittsburgh is roughly 80 miles northwest, and Charlottesville is 110 miles southeast.

When you start to crave the sights and sounds of Mother Nature, load up your daypack and head to Smoke Hole Caverns, located 30 miles away from Oakland. Another option is Blackwater Falls State Park, 20 miles away.

Snowboard or ski down the trails of Timberline Four Season Resort or Bryce Ski Resort. The first is 25 miles from Oakland, while the second is 50 miles.

If you head 10 miles to the northeast of Oakland you will get to Deep Creek Lake State Park. A trip here gives you the chance to visit Wisp Resort and Thousand Acres Lakeside Golf Course. If you're keen on experiencing even more of the region, go to McHenry and stop by The Drane House and Funland. They are located just 12 miles out of Oakland.

Around 35 miles to the northwest of Oakland is Morgantown, a regional hub where travelers can find West Virginia University, Creative Arts Center and Beverly Hills Memorial Gardens. West Virginia Botanic Garden and Morgantown Farmers Market are also worth calling on.

One of the best ways to enjoy this region's natural landscapes is to go rock climbing or hiking.

As adventure-loving travelers, we're always after an exciting story to impress our co-workers when we get back home. If you try paragliding when you're in Western Maryland, you'll have plenty to talk about.

Rafting and canoeing are some of the exhilarating watersport activities to keep you on the move.

If you plan to visit on on the 4th of July, you better be ready to party. Every year on this day, the entire nation comes together to celebrate Independence Day.

You shouldn't worry about being late for boarding. Just keep in mind that the closest airport is 35 miles to the northwest.

Accommodation in Oakland

It might be a bit difficult finding accommodation in Oakland itself, as there are currently no vacancies showing up on Expedia's up-to-the-minute database. However, If you're able to commute, you can rest your head at the Inn At Deep Creek, 5 miles away in Deer Park.


Top Hotel Deals

See all 283 Hotels in Oakland
Inn At Deep Creek $95
Inn At Deep Creek

Inn At Deep Creek

19638 Garrett Hwy, Oakland
     
    3.9
    of 5, from 120 reviews
    2.5 out of 5.0

    Located in the heart of Oakland, this hotel is within 9 mi (15 km) of Wisp Resort, Deep Creek Lake State Park, and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area is 12.3 mi (19.8 km) away.

    The Garrett Inn $68
    The Garrett Inn

    The Garrett Inn

    17848 Garrett Highway, Oakland
       
      4.7
      of 5, from 52 reviews
      2.5 out of 5.0

      Situated in Oakland, this motel is within 12 mi (20 km) of Wisp Resort, Thousand Acres Lakeside Golf Course, and Cranesville Swamp Natural Area. Big Run State Park and New Germany State Park are also within 20 mi (32 km).

      Oak Mar Motel $84
      Oak Mar Motel

      Oak Mar Motel

      208 N 3rd Street, Oakland
         
        4.5
        of 5, from 20 reviews
        2.0 out of 5.0

        Situated in Oakland, this motel is 11.2 mi (18 km) from Cranesville Swamp Natural Area and 11.9 mi (19.1 km) from Cathedral State Park. Thousand Acres Lakeside Golf Course is 14.6 mi (23.5 km) away.

        Luxurous 5 Bedroom Mountain Home Showcases Breathtaking Panoramic Lake Views
        Luxurous 5 Bedroom Mountain Home Showcases Breathtaking Panoramic Lake Views

        Luxurous 5 Bedroom Mountain Home Showcases Breathtaking Panoramic Lake Views

        , Oakland
           
          4.7
          of 5, from 3 reviews
          0.0 out of 5.0

          Situated in Oakland, this vacation home is close to Deep Creek Lake State Park. Area attractions also include Thousand Acres Lakeside Golf Course and Wisp Resort.

          Wispy Mountain Hop @ Deep Creek Lake
          Wispy Mountain Hop @ Deep Creek Lake

          Wispy Mountain Hop @ Deep Creek Lake

          , McHenry
             
            0.0 out of 5.0

            Situated in Oakland, this chalet is close to Wisp Resort. Area attractions also include Deep Creek Lake State Park.

            Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!
            Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!

            Stylish Townhome With Hot Tub Conveniently Located to Area Attractions!

            , Oakland
               
              4.0
              of 5, from 1 reviews
              0.0 out of 5.0

              Situated in Oakland, this vacation home is close to Deep Creek Lake State Park and Thousand Acres Lakeside Golf Course. Area attractions also include Wisp Resort.

              Centrally Located Log Home With Indoor Hot Tub
              Centrally Located Log Home With Indoor Hot Tub

              Centrally Located Log Home With Indoor Hot Tub

              , Oakland
                 
                5.0
                of 5, from 2 reviews
                0.0 out of 5.0

                Situated in Oakland, this vacation home is close to Deep Creek Lake State Park and Thousand Acres Lakeside Golf Course. Area attractions also include Wisp Resort.

                Mountaineer Will Make an Adventurer out of You! Youll Love the Lush Natural Splendor all Around!
                Mountaineer Will Make an Adventurer out of You! Youll Love the Lush Natural Splendor all Around!

                Mountaineer Will Make an Adventurer out of You! Youll Love the Lush Natural Splendor all Around!

                , OAKLAND
                   
                  0.0 out of 5.0

                  Situated in a rural location, this vacation home is close to Deep Creek Lake State Park and Wisp Resort. Area attractions also include Thousand Acres Lakeside Golf Course.

                  Top Deals on Flights

                  These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.