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
Cozy Long Pond Cottage: private mooring & shared dock
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Lakefront, Stunning Home only 30 min to Sugarloaf!
Private and Calming Waterfront to the Rescue!
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Lake House Wooded Vacation Retreat and Nature Escape
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 | 120 Holiday Homes |
---|---|
Lowest Price | AU$405 |
Highest Price | AU$504 |
Popular accommodation | Cozy Long Pond Cottage: private mooring & shared dock, Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK, Lakefront, Stunning Home only 30 min to Sugarloaf!, Private and Calming Waterfront to the Rescue!, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH, Lake House Wooded Vacation Retreat and Nature Escape |
Top Locations for Holiday Homes in Oakland
More accommodations in Oakland
Top trending hotels in Oakland
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Cozy Long Pond Cottage: private mooring & shared dock
Central Maine Apartment offering 4 Seasons of Fun.
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
More ways to explore Oakland
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.