Photo by KM Moore

Oakland vacation rentals

We found 1,564 vacation rentals — enter your dates for availability

Select from 649 houses, 57 condos, and other vacation rentals to find the perfect place for your stay in Oakland. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for spending time at your vacation home, which might include a garden and WiFi. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Oakland

Showing deals for:Aug 22 - Aug 29
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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.

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.

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.

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.

Transportation to and around Oakland

The nearest airport is in Morgantown, WV (MGW-Morgantown Municipal), located 31.8 mi (51.2 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Elkins, WV (EKN-Randolph County), which is 43.3 mi (69.7 km) away.

Frequently asked questions

What is the best area to stay in Oakland when booking a vacation rental?
Blakeslee is one of the most sought-after locations for a vacation home in Oakland. Spend your break here and enjoy all the privacy and convenience that comes with having an entire place to yourself.
What is the most popular type of vacation rental accommodation in Oakland?
Condos are the most popular type of vacation rental in Oakland, according to our data. Even if you’ve got a different idea about what you want, Vrbo has properties in loads of shapes and sizes. Browse our options to find your perfect Oakland pad.
How much does it cost to rent a vacation rental in Oakland?
The average price for a vacation rental in Oakland can vary depending on factors such as season, length of stay and property type. Whether you’re searching for a sprawling villa with a pool or an apartment just enough for two, just add your travel dates to see stays with exceptional value.
How much does it cost to rent a beach house in Oakland?
The average price for a vacation rental close to the beach in Oakland depends on when you’re traveling and the type and size of property you’re looking for. You can quickly and easily find prices on Vrbo by entering your destination and preferred travel dates. Then use the handy filter tool to pick the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.
Are there pet-friendly vacation rentals in Oakland?
There certainly are. Choose from 521 vacation homes that roll out the welcome mat in Oakland on Vrbo. Our furry kids deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to book a place where your puppy dog can share in the good times.
Can I rent a house with a pool in Oakland?
Add a whole new level of fun to your adventure by booking your family into one of the 264 houses with a private pool in Oakland. Use our handy search filter to find the kind of property you want on Vrbo, and then spend carefree days splashing around in a swimming pool that’s just for you.
What are popular rental amenities in Oakland?
The most popular rental amenities people search for in Oakland include a water view, a sauna and a garden. Whether you’re taking a trip with family, pals or even pets, Vrbo vacation homes include the best amenities for chilling out with the people that matter most.
Are there large group vacation rentals in Oakland?
Oakland has 286 vacation homes that can cater to 10 or more people. These stays come with enough space to share good times with loved ones.
Are there vacation rentals in Oakland that welcome kids?
With 521 family-friendly vacation properties to select from in Oakland, now is the perfect time to introduce the little ones to the thrills of travel. Simply click on our “Properties good for families” filter box to discover stays packed with conveniences perfect for traveling families, like full kitchens, patios, entertainment areas and hot tubs.
What are the top attractions for families in Oakland?
Give the kids a good time at these popular family-friendly attractions in Oakland:

  • Swallow Falls State Park
  • Herrington Manor State Park

Are there one-bedroom vacation rentals in Oakland?
Oakland has 82 one-bedroom rentals available. Often positioned in prime spots thanks to their compact size, a one-bedroom vacation property is great if you’re traveling with your partner or a pal. And with comforts like kitchens and more privacy than a standard hotel, you’ll be able to relax while exploring this incredible destination.
Can I find two-bedroom vacation rentals in Oakland?
Select from 40 two-bedroom properties in Oakland. Put the kids in the second room or maybe fill it with a couple of your favorite people. There’s a comfy spot for whoever’s fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Oakland?
Oakland has 447 vacation rentals with WiFi, so you’ll be able to stay connected when you’re away. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movie blockbusters to scrolling social media, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Oakland?
Oakland has 460 vacation rentals where you’ll be able to spend your days in air-conditioned comfort. To locate a property on Vrbo that offers this amenity, enter your desired travel dates and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Oakland?
The minimum age is typically 16, 18 or 21. It can vary between properties on Vrbo, so look at the rules of your chosen Oakland vacation home before you book.
How long can I rent a vacation rental in Oakland for?
The amount of time you can rent an Oakland vacation home for is up to the property. Just enter your preferred travel dates to view options that offer long-term stays. They feature all you need to make your extended getaway more convenient and enjoyable, such as air conditioning and laundries. Some Vrbo vacation rentals may also offer weekly or monthly discounted prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in Oakland?
On Vrbo, we’ve got some amazing discounts and bargains for Oakland. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re after a short getaway or a longer stay, Vrbo has options for every style and budget.

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