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
Stay at this vacation home in Oakland. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Hot tub, fire pit, lakefront, dock, pet friendly and more!

Hot tub, fire pit, lakefront, dock, pet friendly and more!

Oakland
Stay at this vacation home in Oakland. Enjoy breakfast (surcharge), concierge services, and patios. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
Hot tub, fire pit, lakefront, dock, pet friendly and more!
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
Stay at this vacation home in Oakland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Deep Creek ...
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
New: Lakefront Luxury Home with Private Indoor Heated Pool!

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy private pools, breakfast (surcharge), and concierge services. Popular attractions Deep Creek ...
New: Lakefront Luxury Home with Private Indoor Heated Pool!
Dog-friendly house on the lake, central AC, & EV charger

Dog-friendly house on the lake, central AC, & EV charger

Oakland
Stay at this vacation home in Oakland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
Dog-friendly house on the lake, central AC, & EV charger
Lakefront, dog friendly, dock slip, hot tub, and fire pit

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Wisp ...
Lakefront, dog friendly, dock slip, hot tub, and fire pit
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
Stay at this vacation home in Oakland. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Deep Creek Lake and Deep Creek Lake ...
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace

Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace

Oakland
Stay at this vacation home in Oakland. Enjoy a pool table, patios, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace
Stunning 7 Bedroom  6.5 Bath Lakefront Home with Dock Slip

Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a water park, and a garden. Popular attractions Deep Creek Lake and Deep Creek ...
Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip
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.

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
599 Holiday Homes
Lowest Price
NZ$207
Highest Price
NZ$255
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Hot tub, fire pit, lakefront, dock, pet friendly and more!, Modern house on the lake with private dock, hot tub, air hockey & central AC, New: Lakefront Luxury Home with Private Indoor Heated Pool!, Dog-friendly house on the lake, central AC, & EV charger, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi, Spacious home near Wisp/Deep Lake SP with hot tub, pool table, & fireplace, Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock Slip

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 NZ$207 per night from 6 Apr to 7 Apr
NZ$207
includes taxes & fees
6 Apr - 7 Apr
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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 NZ$255 per night from 16 Apr to 17 Apr
NZ$255
includes taxes & fees
16 Apr - 17 Apr
Stay at this motel in Oakland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Broadford Park and Broadford Recreation Area are located ...
Riverside Suites
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
Stay at this vacation home in Oakland. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
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
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Deep Creek Lake ...
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.