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See your best deals – start by selecting your hotel
See your best deals – start by selecting your hotel
See your best deals – start by selecting your hotel

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Oakland Vacation Packages

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

Save Time and Money with an Oakland Package Deal

Get immediate savings when you purchase package deals with Expedia. Most smart travelers notice that flight and hotel packages are the best way to save time and money. Experience more on your Oakland trip with the extra cash.

If you take advantage of a deal, you can save as much as $583.

Our expansive database contains up to 400 partner airlines and 321,000 hotels across the planet.

For Oakland vacations, you'll have a hard time finding anything more cost-effective than the prices at Expedia.

Need more time to decide? You won't pay us a cancellation fee when you change almost any hotel reservation.

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.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 286 Properties in Oakland
The Garrett Inn $88
The Garrett Inn

The Garrett Inn

17848 Garrett Highway, Oakland
     
    4.7
    of 5, from 65 reviews
    2.5 out of 5.0

    Situated in Oakland, this motel is 4.7 mi (7.6 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area is 11.9 mi (19.2 km) away.

    Arctic Retreat- 3 Bedroom Lake Access Home in Tranquil Wooded Setting
    Arctic Retreat- 3 Bedroom Lake Access Home in Tranquil Wooded Setting

    Arctic Retreat- 3 Bedroom Lake Access Home in Tranquil Wooded Setting

    , OAKLAND
       
      0.0 out of 5.0

      Situated in a rural location, this romantic vacation home is 2.3 mi (3.7 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area and Big Run State Park are also within 16 mi (25 km).

      Log Home With Indoor Hot Tub Close to Activities
      Log Home With Indoor Hot Tub Close to Activities

      Log Home With Indoor Hot Tub Close to Activities

      , Oakland
         
        2.0
        of 5, from 1 reviews
        0.0 out of 5.0

        Situated in Oakland, this vacation home is 2.3 mi (3.7 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area and Big Run State Park are also within 16 mi (25 km).

        Ski In/ski Out With Lake Access
        Ski In/ski Out With Lake Access

        Ski In/ski Out With Lake Access

        , McHenry
           
          5.0
          of 5, from 1 reviews
          0.0 out of 5.0

          Situated in Oakland, this vacation home is 1.2 mi (2 km) from Wisp Resort and within 12 mi (20 km) of Deep Creek Lake State Park and Cranesville Swamp Natural Area. Thousand Acres Lakeside Golf Course and Casselman River Bridge State Park are also within 25 mi (40 km).

          Bunbury Cottage- 3 Bedroom Lake Acess Home Near Swallow Falls State Park
          Bunbury Cottage- 3 Bedroom Lake Acess Home Near Swallow Falls State Park

          Bunbury Cottage- 3 Bedroom Lake Acess Home Near Swallow Falls State Park

          , OAKLAND
             
            0.0 out of 5.0

            Situated in a rural location, this romantic vacation home is 6 mi (9.6 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Cranesville Swamp Natural Area. Thousand Acres Lakeside Golf Course is 10.5 mi (16.9 km) away.

            Inn At Deep Creek $169
            Inn At Deep Creek

            Inn At Deep Creek

            19638 Garrett Hwy, Oakland
               
              3.9
              of 5, from 126 reviews
              2.5 out of 5.0

              Located in the heart of Oakland, this hotel is 2.8 mi (4.5 km) from Deep Creek Lake State Park and within 9 mi (15 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area is 12.3 mi (19.8 km) away.

              Conveniently Located log Cabin With Outdoor hot Tub!
              Conveniently Located log Cabin With Outdoor hot Tub!

              Conveniently Located log Cabin With Outdoor hot Tub!

              , Oakland
                 
                4.3
                of 5, from 3 reviews
                0.0 out of 5.0

                Situated in Oakland, this vacation home is 4.6 mi (7.4 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area is 11.8 mi (19 km) away.

                Swallow Falls Inn Cabin 2- 1 Bedroom Cabin Near Swallow Falls State Park
                Swallow Falls Inn Cabin 2- 1 Bedroom Cabin Near Swallow Falls State Park

                Swallow Falls Inn Cabin 2- 1 Bedroom Cabin Near Swallow Falls State Park

                , OAKLAND
                   
                  0.0 out of 5.0

                  Situated in a rural location, this romantic cabin is within 9 mi (15 km) of Cranesville Swamp Natural Area, Wisp Resort, and Deep Creek Lake State Park. Thousand Acres Lakeside Golf Course and Cathedral State Park are also within 20 mi (32 km).

                  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.