Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

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 ...
Opens in a new windowLevel lakefront, family-friendly, hot tub, low fees, private dock
Amazing Central Location! Lakefront! Hot tub/dock!

Amazing Central Location! Lakefront! Hot tub/dock!

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 7 minutes from Deep Creek Lake State ...
Opens in a new windowAmazing Central Location! Lakefront! Hot tub/dock!
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.
Opens in a new windowRural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
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Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!

Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!

Oakland
When you stay at this vacation home in Oakland, you'll be on a lake, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Opens in a new windowLog Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!
Loft of Luxury

Loft of Luxury

4 out of 5
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.
Opens in a new windowLoft of Luxury
Mountain Escape | Hot Tub | Game Room | Fire Pit

Mountain Escape | Hot Tub | Game Room | Fire Pit

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.
Opens in a new windowMountain Escape | Hot Tub | Game Room | Fire Pit
Couples Retreat: The HayLoft-  Rustic Escape For 2

Couples Retreat: The HayLoft- Rustic Escape For 2

Oakland
The price is AU$332 per night from 29 Sept to 30 Sept
AU$332
29 Sept - 30 Sept
includes taxes & fees
Located in Oakland, this vacation home is a 2-minute drive from Youghiogheny River and 9 minutes from Oakland Dog Park.
Opens in a new windowCouples Retreat: The HayLoft- Rustic Escape For 2
Triple-T Lodge: Lake Area, Hot Tub, Pool Table, Gas Grill!

Triple-T Lodge: Lake Area, Hot Tub, Pool Table, Gas Grill!

Oakland
When you stay at this vacation home in Oakland, you'll be on a lake, a 1-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State Park.
Opens in a new windowTriple-T Lodge: Lake Area, Hot Tub, Pool Table, Gas Grill!
Luxury Mountain Escape w/ Hot Tub & Fireplaces

Luxury Mountain Escape w/ Hot Tub & Fireplaces

OAKLAND
With a stay at this vacation home in Oakland (Mountainside), you'll be within a 15-minute drive of Deep Creek Lake and Wisp Resort.
Opens in a new windowLuxury Mountain Escape w/ Hot Tub & Fireplaces
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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
450 Holiday Homes
Lowest Price
AU$188
Highest Price
AU$332
Popular accommodation
Level lakefront, family-friendly, hot tub, low fees, private dock, Amazing Central Location! Lakefront! Hot tub/dock!, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi, Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!, Loft of Luxury, Mountain Escape | Hot Tub | Game Room | Fire Pit, Couples Retreat: The HayLoft- Rustic Escape For 2, Triple-T Lodge: Lake Area, Hot Tub, Pool Table, Gas Grill!, Luxury Mountain Escape w/ Hot Tub & Fireplaces

Top trending hotels in Oakland

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy, Oakland, MD
Fully refundableReserve now, pay when you stay
With a stay at Baja Motel in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Mountain Lake Park Town Hall.
Opens in a new windowBaja Motel
The Garrett Inn

The Garrett Inn

2.5 out of 5
17848 Garrett Highway, Oakland, MD
The price is AU$188 per night from 29 Sept to 30 Sept
AU$188
29 Sept - 30 Sept
includes taxes & fees
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.
Opens in a new windowThe Garrett Inn
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 ...
Opens in a new windowNew: Lakefront Luxury Home with Private Indoor Heated Pool!
Save an average of 15% on thousands of hotels when you're signed in
Amazing Central Location! Lakefront! Hot tub/dock!

Amazing Central Location! Lakefront! Hot tub/dock!

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 7 minutes from Deep Creek Lake State ...
Opens in a new windowAmazing Central Location! Lakefront! Hot tub/dock!
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.