Book Holiday Homes in Oakland
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Oakland

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

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Wandering Woods- Dog-friendly 3 bedroom home with lake access and hot tub!

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

Deep Creek Lake Townhome w/ Deck & Water Views

Dog-friendly home near state parks with firepit, pool table, fireplace, & decks

Huge, Beautiful and Quiet Home with Amazing Amenities

Deep Creek Lake views from the elevated deck & deluxe suite - near golf

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
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 | 596 Holiday Homes |
---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp, In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Wandering Woods- Dog-friendly 3 bedroom home with lake access and hot tub!, Dog-friendly house on the lake, central AC, & EV charger, Deep Creek Lake Townhome w/ Deck & Water Views, Dog-friendly home near state parks with firepit, pool table, fireplace, & decks, Huge, Beautiful and Quiet Home with Amazing Amenities, Deep Creek Lake views from the elevated deck & deluxe suite - near golf, Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi |
More accommodations in Oakland
Top trending hotels in Oakland

The Garrett Inn

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

Riverside Suites

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
More ways to explore Oakland
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.