Destination guide

A gateway to untamed Maryland

Surrounded by towering forests and shimmering lakes, Oakland is a laid-back town in the heart of Garrett County. A true all-season destination, it lures sunseekers, snow bunnies and leaf peepers alike. Whether you want to whitewater raft down the Youghiogheny River, hit the slopes at Wisp Resort or simply relax on the deck of your Oakland vacation rentals hideaway, it's an enchanting slice of Maryland. You'll also be an easy hop from Deep Creek Lake, a year-round outdoor playground offering swimming, fishing, boating, hiking and more.

Things to do

Discover Oakland's flourishing arts scene

With its scenic setting and free-spirited lifestyle, Oakland is a hotspot for artists. Check out local talent at the Spruce Forest Artisan Village, where you can wander around historic workshops and chat to resident artists. The Simon Pearce Glassblowing Workshop is another highlight, treating visitors to demonstrations, workshops and a colorful gift store. While nearby Broadford Lake is a favorite with locals, Deep Creek Lake steals the spotlight. It serves up endless family fun, from kayaking and sailing to jet skiing and speed boating.

Activities

Whitewater thrills on the Youghiogheny River

Winding through Maryland, the Youghiogheny River is a hotspot for whitewater rafting. You can take on class IV and V rapids or head downstream for a leisurely paddle. In winter, Oakland transforms into a snow-white wonderland. If you can drag yourself away from the fireplace, Oakland vacation rentals put you just steps from some of Maryland's best snowshoeing and cross-country skiing trails. Skiers and snowboarders flock to Wisp Resort, where you'll find over 30 runs and a challenging terrain park.

Weather

Leaf peeping in Oakland

Every fall, Oakland explodes in a sea of reds, yellows and golds. In fact, it's regularly named one of the best places in America to admire fall foliage. The town celebrates with the annual Autumn Glory Festival, a 5-day celebration filled with music, art, parades, street stalls and, of course, fiery fall colors. Summer is also a busy time, especially over the US school holidays. Planning a family vacation? With plenty of pet-friendly Oakland vacation rentals to choose from, whisking the whole family to Maryland has never been easier.

Natural features

Reel in monster-sized trout

Set in Garrett County, Oakland is tucked away in a scenic valley. It's surrounded by white pines, hemlocks, maples, hickories and, of course, plenty of oaks. The town is just 10 miles from Deep Creek Lake, one of Maryland's most visited summer destinations. The Youghiogheny River carves through the landscape and is brimming with monster-sized trout. From family-friendly walks to backcountry hikes, Garrett County is surrounded by national parks and state forests. You can mountain bike in Swallow Falls State Park, hike through heritage-listed oak groves in Garrett State Forest or relax by the lake in Broadford Park.

How to get there

Transportation to and around Oakland

Fly into Morgantown, WV (MGW-Morgantown Municipal), the closest airport, located 33.3 mi (53.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Elkins, WV (EKN-Randolph County), which is 42.8 mi (68.9 km) away.

Where to stay around Oakland?

Our 2019 property listings offer a large selection of 1,218 vacation rentals near Oakland. From 804 Houses to 130 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 HomeAway.

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: 56 vacation rentals
  • The View: 171 vacation rentals
  • Timberline: 177 vacation rentals
  • Mountainside: 163 vacation rentals
  • Waterfront Greens: 98 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Oakland?

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

  • Swallow Falls State Park: 1,149 vacation rentals
  • Blackwater Falls State Park: 299 vacation rentals
  • Deep Creek Lake State Park: 1,104 vacation rentals
  • Smoke Hole Caverns: 315 vacation rentals
  • Wisp Resort: 1,064 vacation rentals

But there are many other points of interest around Oakland listed on HomeAway 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. HomeAway has 804 Houses in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Cabins: 130 rentals available
  • Cottages: 130 rentals available
  • Bungalows: 130 rentals available

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

Can I find a vacation rental with pool in Oakland?

Yes, you can select your preferred vacation rental with pool among our 203 vacation rentals with pool available in Oakland. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Oakland