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 kitchens and swimming pools. Prices start at $192 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 2020 property listings offer a large selection of 1,229 vacation rentals around Oakland. From 89 cabin rentals to 837 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a lakeside property in Oakland?

Skip the beach and stay by a lake instead. Kick back, chill out and soak in the views. Vrbo has 545 vacation properties near lakes available. Of course, that might not be your style. Luckily, Vrbo has a selection of other options, including:

  • 518 mountainside vacation rentals.
  • 444 rural vacation rentals.
  • 428 lakefront vacation rentals.

Can I rent a house in Oakland?

If you're seeking a home away from home this trip, renting a house is a fantastic idea. You and your crew will have the space you need for all sorts of vacation activities. There are 1,031 options currently available on Vrbo. Prices start from $38 a night. If that doesn't agree with your posse's taste, we've got a number of other rental options available, such as:

  • Townhome: 166 vacation homes. Prices start from $98 per night.
  • Cabin: 87 vacation homes. Prices start from $49 per night.
  • Condo: 86 vacation homes. Prices start from $116 per night.

Can I stay in Oakland in a large group?

Sometimes it can be tough finding time to relax with your family and close friends. A group getaway is a fantastic opportunity to get together. If you were hoping to stay under the same roof, Vrbo has options. House vacation homes are the preferred choice here for big groups of guests. Our database currently has 212 available. The lodging options that are perfect for large numbers here include:

  • If yours is a group of 12, we've got 251 vacation homes appropriate for that size. Spend a night for as little as $38.
  • After a vacation rental for 10 people? We have 247 that will suit. You can get one for as low as $116 per night.
  • Seeking rental properties catering to 8 people? You'll be pleased to hear we have 221 that'll be perfect. You can bag one from just $49 per night.

So don't fret! When you travel with us you can bring your mom, your grandma and all your friends to Oakland.

Where are the cheapest rentals in Oakland?

Pint-sized hotel rooms are no place to spend those precious vacation moments! Explore our thrifty rentals today and make sure everyone has room to spread out. When it comes to seeking out an awesome deal, the first place you look ought to be Waterside At Wisp. Here, Vrbo has 205 rentals at an average price of $198 per night. You'll find another 160 Vrbo rentals waiting for you in or around Old Timberline. The average price in this area is $210 a night.

Explore destinations around Oakland