Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

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,
Hot tub, fire pit, lakefront, dock, pet friendly and more!

Hot tub, fire pit, lakefront, dock, pet friendly and more!

Oakland
With a stay at this vacation home in Oakland (Blakeslee), you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Hot tub, fire pit, lakefront, dock, pet friendly and more!
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
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New: Lakefront Luxury Home with Private Indoor Heated Pool!

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, a 2-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State ...
New: Lakefront Luxury Home with Private Indoor Heated Pool!
Dog-friendly house on the lake, central AC, & EV charger

Dog-friendly house on the lake, central AC, & EV charger

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Dog-friendly house on the lake, central AC, & EV charger
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 Wild River Natural Environmental ...
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Oakland
When you stay at this vacation home in Oakland, you'll be in the mountains, a 3-minute drive from Deep Creek Lake and 10 minutes from Wisp Resort.
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace

Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace

Oakland
With a stay at this vacation home in Oakland (Silver Ridge), you'll be a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.
Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace
Stunning 7 Bedroom  6.5 Bath Lakefront Home with Dock Slip

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Oakland
With a stay at this vacation home, you'll be centrally located in Oakland, a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State ...
Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip
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
597 Holiday Homes
Lowest Price
AU$188
Highest Price
AU$214
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Hot tub, fire pit, lakefront, dock, pet friendly and more!, Modern house on the lake with private dock, hot tub, air hockey & central AC, New: Lakefront Luxury Home with Private Indoor Heated Pool!, Dog-friendly house on the lake, central AC, & EV charger, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi, Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace, Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

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$188 per night from 31 Mar to 1 Apr
AU$188
includes taxes & fees
31 Mar - 1 Apr
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
Riverside Suites

Riverside Suites

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is AU$214 per night from 31 Mar to 1 Apr
AU$214
includes taxes & fees
31 Mar - 1 Apr
With a stay at Riverside Suites in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Mountain Lake Park Town Hall.
Riverside Suites
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,
Save an average of 15% on thousands of hotels when you're signed in
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
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.