Discover a selection of 1,000 vacation rentals in Oakland, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $150 per night, and cabins and houses are popular options for a stay in Oakland. Either way, you'll find a rental for everyone's needs.
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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.

How many vacation rentals are available around Oakland, MD?

Our 2021 property listings offer a large selection of 1,228 vacation rentals around Oakland. From 83 cabin rentals to 1,105 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Mountainside: 169 vacation rentals
  • Blakeslee: 52 vacation rentals
  • Paradise Point: 193 vacation rentals
  • Silver Ridge: 206 vacation rentals
  • The View: 170 vacation rentals

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

Can I rent Cabins in Oakland?

Yes, of course. Vrbo has 83 Cabins in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Houses: 1,105 rentals available
  • Cottages: 83 rentals available
  • Bungalows: 83 rentals available

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

Can I find a vacation rental with pool in Oakland?

Yes, you can select your preferred vacation rental with pool among our 187 vacation rentals with pool available in Oakland. Please use our search bar to access the selection of vacation rentals available.