Oakland, MD, USA

Oakland, MD, USA

We found 1,076 vacation rentals — enter your dates for availability

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Find the best place to stay — Oakland

Where to stay around Oakland, MD?

Our 2018 property listings offer a large selection of 1,076 vacation rentals near Oakland. From 759 houses to 124 townhomes, 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: 57 vacation rentals
  • The View: 117 vacation rentals
  • Waterfront Greens: 85 vacation rentals
  • Old Timberline: 159 vacation rentals
  • North Glade Hills: 80 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 5 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Deep Creek Lake State Park: 1,010 vacation rentals
  • Wisp Resort: 1,033 vacation rentals
  • Canaan Valley Ski Resort: 388 vacation rentals
  • Blackwater Falls State Park: 369 vacation rentals
  • Canaan Valley Resort State Park: 388 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 759 houses in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Townhomes: 124 rentals available
  • Cabins: 80 rentals available
  • Condos: 71 rentals available

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

Can I rent golf rental rentals in Oakland?

Absolutely, VRBO has 570 golf rental rentals in Oakland. You have also many other possibilities in Oakland area, including:

  • Ski rental rentals: 416 rentals
  • Lakefront rentals: 404 rentals
  • Lake view rentals: 291 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 1,060 vacation rentals with online bookable available in Oakland. Please use our search bar to access the selection of vacation rentals available.