Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

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
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
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
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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,
Central Lake House with Private Dock! Walk to Area Hot Spots!

Central Lake House with Private Dock! Walk to Area Hot Spots!

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.
Central Lake House with Private Dock! Walk to Area Hot Spots!
Elegant Home Away: Hot Tub, Game Room, Kid Friendly!

Elegant Home Away: Hot Tub, Game Room, Kid Friendly!

Oakland
Located in Oakland, this vacation home is on a lake, within a 5-minute walk of Youghiogheny River and Youghiogheny Wild River Natural Environmental Area.
Elegant Home Away: Hot Tub, Game Room, Kid Friendly!
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
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 a 2-minute drive from Deep Creek Lake and 10 minutes from Youghiogheny Wild River Natural Environmental ...
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
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 Wild River Natural Environmental ...
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
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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
505 Holiday Homes
Lowest Price
AU$193
Highest Price
AU$196
Popular accommodation
Lakefront, dog friendly, dock slip, hot tub, and fire pit, Lakefront/Dock/Amazing views HotTub, Deep Creek Lake Townhome w/ Deck & Water Views, In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Central Lake House with Private Dock! Walk to Area Hot Spots!, Elegant Home Away: Hot Tub, Game Room, Kid Friendly!, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi, Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table, Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

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$196 per night from 26 Jan to 27 Jan
AU$196
includes taxes & fees
26 Jan - 27 Jan
With a stay at The Garrett Inn in Oakland, you'll be near the beach, within a 10-minute drive of Deep Creek Lake and Mount Nebo Wildlife Management Area.
The Garrett Inn
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
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
Riverside Suites

Riverside Suites

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 7 Feb to 8 Feb
AU$193
includes taxes & fees
7 Feb - 8 Feb
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
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.

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^Subject to availability and chosen travel dates.