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,
Deep Creek Lake Townhome w/Deck & Water Views

Deep Creek Lake Townhome w/Deck & Water Views

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.
Deep Creek Lake Townhome w/Deck & Water Views
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table

Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table

Oakland
With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Funland.
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
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Oakland Retreat ~ 13 Mi to Deep Creek Lake!

Oakland Retreat ~ 13 Mi to Deep Creek Lake!

Oakland
With a stay at this vacation home in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Wolf Den Run State Park.
Oakland Retreat ~ 13 Mi to Deep Creek Lake!
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
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
Beautiful Lake View w/Hot tub, Fireplace,& firepit

Beautiful Lake View w/Hot tub, Fireplace,& firepit

Oakland
With a stay at this vacation home, you'll be centrally located in Oakland, a 4-minute drive from Deep Creek Lake and 11 minutes from Wisp Resort.
Beautiful Lake View w/Hot tub, Fireplace,& firepit
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
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!
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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
459 Holiday Homes
Lowest Price
AU$169
Highest Price
AU$169
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Deep Creek Lake Townhome w/Deck & Water Views, Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table, Oakland Retreat ~ 13 Mi to Deep Creek Lake!, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Lakefront/Dock/Amazing views HotTub, Beautiful Lake View w/Hot tub, Fireplace,& firepit, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi, New: Lakefront Luxury Home with Private Indoor Heated Pool!

Top trending hotels in Oakland

The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is AU$169 per night from 22 May to 23 May
AU$169
per night
22 May - 23 May
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 a 2-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.
Dog-friendly cabin with private hot tub, Ping-Pong & lake 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,
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.

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^Subject to availability and chosen travel dates.