Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland
With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny River.
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Serene Mountain Escape: Hot Tub, Foosball, Views

Serene Mountain Escape: Hot Tub, Foosball, Views

Oakland
When you stay at this vacation home in Oakland, you'll be in the mountains, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Serene Mountain Escape: Hot Tub, Foosball, Views
Lakefront/Dock/Amazing views HotTub

Lakefront/Dock/Amazing views HotTub

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Lakefront/Dock/Amazing views HotTub
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Lakefront, dog friendly, dock slip, hot tub, and fire pit

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Oakland
With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny River.
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Level lakefront, family-friendly, hot tub, low fees, private dock

Level lakefront, family-friendly, hot tub, low fees, private dock

Oakland
With a stay at this vacation home in Oakland (Paradise Point), you'll be a 1-minute drive from Deep Creek Lake and 9 minutes from Deep Creek Lake State ...
Level lakefront, family-friendly, hot tub, low fees, private dock
Modern house on the lake with private dock, hot tub, air hockey & central AC

Modern house on the lake with private dock, hot tub, air hockey & central AC

Oakland
With a stay at this vacation home in Oakland (Mountainside), you'll be a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Modern house on the lake with private dock, hot tub, air hockey & central AC
Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Oakland
With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.
Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River
Private Lodge sleeps 25 guests Spectacular Views

Private Lodge sleeps 25 guests Spectacular Views

Oakland
Located in Oakland, this vacation home is within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Private Lodge sleeps 25 guests Spectacular Views
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland
With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 7 minutes from Wisp Resort.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Don't see what you're looking for?
See all available properties in Oakland
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oakland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakland Holiday Homes essential information

Accommodation
498 Holiday Homes
Lowest Price
AU$197
Highest Price
AU$197
Popular accommodation
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit, Serene Mountain Escape: Hot Tub, Foosball, Views, Lakefront/Dock/Amazing views HotTub, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Level lakefront, family-friendly, hot tub, low fees, private dock, Modern house on the lake with private dock, hot tub, air hockey & central AC, Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River, Private Lodge sleeps 25 guests Spectacular Views, In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Top trending hotels in Oakland

The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 5 Jan to 6 Jan
AU$197
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at The Garrett Inn in Oakland, you'll be near the beach, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
The Garrett Inn
Dog-friendly cabin with private hot tub, Ping-Pong & lake views

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

Oakland
With a stay at this cabin in Oakland (Paradise Point), you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Modern house on the lake with private dock, hot tub, air hockey & central AC

Modern house on the lake with private dock, hot tub, air hockey & central AC

Oakland
With a stay at this vacation home in Oakland (Mountainside), you'll be a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Modern house on the lake with private dock, hot tub, air hockey & central AC
Save an average of 15% on thousands of hotels when you're signed in
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland
With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny River.
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Don't see what you're looking for?
See all available properties in Oakland
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.