Find the best place to stay — Oakland

Where to stay around Oakland, MD?

Our 2018 property listings offer a large selection of 1,069 vacation rentals near Oakland. From 728 houses to 115 cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oakland for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Oakland?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Oakland:

  • Blakeslee: 55 vacation rentals
  • The View: 116 vacation rentals
  • Canaan Valley Ski Resort: 28 vacation rentals
  • Old Timberline: 158 vacation rentals
  • Mountainside: 146 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Oakland?

VRBO offers a large selection of vacation rentals near lovely places in Oakland. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Wisp Resort: 1,018 vacation rentals
  • Deep Creek Lake State Park: 998 vacation rentals
  • Timberline Four Season Resort: 365 vacation rentals
  • Cathedral State Park: 1,062 vacation rentals
  • Blackwater Falls State Park: 362 vacation rentals

But there are many other points of interest around Oakland listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent houses in Oakland?

Yes, of course. VRBO has 728 houses in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Cabins: 115 rentals available
  • Townhomes: 113 rentals available
  • Condos: 66 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including chalets and more.

Can I rent golf rental rentals in Oakland?

Absolutely, VRBO has 558 golf rental rentals in Oakland. You have also many other possibilities in Oakland area, including:

  • Ski rentals: 528 rentals
  • Lakefront rentals: 354 rentals
  • Lake view rentals: 350 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Oakland?

Yes, you can select your prefered vacation rental with online bookable among our 1,053 vacation rentals with online bookable available in Oakland. Please use our search bar to access the selection of vacation rentals available.

    Explore the lakeside setting in Oakland

    The lake and riverfront provide a pleasant backdrop to your vacation home in Oakland. Renowned for its rafting, skiing and ecotours, this city welcomes all visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

    Sightseeing in and around Oakland

    Do you want to discover attractions to visit in the area? Venture out of your vacation home and experience everything that Oakland has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

    • Thousand Acres Lakeside Golf Course (9.3 mi / 14.9 km)
    • Wisp Resort (11.7 mi / 18.9 km)
    • Hovatter's Wildlife Zoo (20.4 mi / 32.9 km)
    • Timberline Four Season Resort (23.9 mi / 38.5 km)
    • Canaan Valley Ski Resort (25.6 mi / 41.2 km)

    Exploring the natural landscape of Oakland

    Travelers enjoy Oakland for its lakeside setting and riverfront. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oakland is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

    • Cathedral State Park (8.9 mi / 14.2 km)
    • Deep Creek Lake State Park (10.5 mi / 16.8 km)
    • Cranesville Swamp Natural Area (11.2 mi / 18 km)
    • Fairfax Stone Historical Monument Park (14.5 mi / 23.3 km)
    • Big Run State Park (17.2 mi / 27.6 km)
    • Blackwater Falls State Park (19.9 mi / 32.1 km)