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,
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
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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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
Peaceful centrally located home near summer and winter outdoor activities

Peaceful centrally located home near summer and winter outdoor activities

2 out of 5
Oakland
Located in Oakland, this vacation home is in a rural location, within a 15-minute drive of Cranesville Swamp Natural Area and Swallow Falls State Park.
Peaceful centrally located home near summer and winter outdoor activities
Foxcroft: New, Lake Access w. Dock Slip, Hot Tub, Pool Table

Foxcroft: New, Lake Access w. Dock Slip, Hot Tub, Pool Table

Oakland
With a stay at this vacation home in Oakland, you'll be in the mountains, within a 5-minute drive of Deep Creek Lake and Youghiogheny River.
Foxcroft: New, Lake Access w. Dock Slip, Hot Tub, Pool Table
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
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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$189
Highest Price
AU$248
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Level lakefront, family-friendly, hot tub, low fees, private dock, Deep Creek Lake Townhome w/ Deck & Water Views, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Lakefront/Dock/Amazing views HotTub, Beautiful Lake View w/Hot tub, Fireplace,& firepit, Peaceful centrally located home near summer and winter outdoor activities, Foxcroft: New, Lake Access w. Dock Slip, Hot Tub, Pool Table, Dog-friendly house on the lake, central AC, & EV charger

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$189 per night from 25 Nov to 26 Nov
AU$189
includes taxes & fees
25 Nov - 26 Nov
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$248 per night from 2 Dec to 3 Dec
AU$248
includes taxes & fees
2 Dec - 3 Dec
With a stay at Riverside Suites in Oakland, you'll be within a 15-minute drive of Deep Creek Lake and Garrett Regional Medical Center.
Riverside Suites
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
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
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.