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.
Opens in a new windowIn the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
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
5BR lakefront retreat with hot tub, sauna, & dock

5BR lakefront retreat with hot tub, sauna, & dock

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 Wisp Resort.
Opens in a new window5BR lakefront retreat with hot tub, sauna, & dock
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Couples Retreat: The HayLoft-  Rustic Escape For 2

Couples Retreat: The HayLoft- Rustic Escape For 2

Oakland
The price is AU$365 per night from 16 Nov to 17 Nov
AU$365
16 Nov - 17 Nov
includes taxes & fees
Located in Oakland, this farm stay is a 4-minute drive from Youghiogheny River and 10 minutes from Oakland Dog Park.
Opens in a new windowCouples Retreat: The HayLoft- Rustic Escape For 2
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, within a 15-minute drive of Deep Creek Lake and Wisp Resort.
Opens in a new windowNew: Lakefront Luxury Home with Private Indoor Heated Pool!
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 ...
Opens in a new windowLakefront, dog friendly, dock slip, hot tub, and fire pit
Charming Dog Friendly Cottage w/ Dock & Fire Pit

Charming Dog Friendly Cottage w/ Dock & Fire Pit

Mc Henry
When you stay at this vacation home in Oakland, you'll be on a lake, a 3-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.
Opens in a new windowCharming Dog Friendly Cottage w/ Dock & Fire Pit
Private & Spacious 8-bedroom lodge with amazing outdoor space and game room

Private & Spacious 8-bedroom lodge with amazing outdoor space and game room

Oakland
Located in Oakland, this vacation home is within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Opens in a new windowPrivate & Spacious 8-bedroom lodge with amazing outdoor space and game room
Dog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer

Dog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer

Oakland
With a stay at this vacation home in Oakland, you'll be a 2-minute drive from Deep Creek Lake and 8 minutes from Deep Creek Lake State Park.
Opens in a new windowDog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer
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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$365
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi, 5BR lakefront retreat with hot tub, sauna, & dock, Couples Retreat: The HayLoft- Rustic Escape For 2, New: Lakefront Luxury Home with Private Indoor Heated Pool!, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Charming Dog Friendly Cottage w/ Dock & Fire Pit, Private & Spacious 8-bedroom lodge with amazing outdoor space and game room, Dog-friendly townhouse with wood-burning fireplace, balcony & washer/dryer

Top trending hotels in Oakland

Baja Motel

Baja Motel

2 out of 5
1501 Maryland Hwy, Oakland, MD
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 19 Nov to 20 Nov
AU$188
19 Nov - 20 Nov
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
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!
Save an average of 15% on thousands of hotels when you're signed in
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
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.