Book Holiday Homes in Oakland
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Oakland

Belgrade Lake house with Dock!

3 Bedroom year round lakefront home on Three Mile Pond with private dock

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

Cozy Cottage on water's edge of Lake Cobbosseecontee

Every window has a spectacular lake view Low fees

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Lovely Home on Androscoggin Lake
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 | 155 Holiday Homes |
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Lowest Price | AU$492 |
Highest Price | AU$719 |
Popular accommodation | Belgrade Lake house with Dock!, 3 Bedroom year round lakefront home on Three Mile Pond with private dock, Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly, Cozy Cottage on water's edge of Lake Cobbosseecontee, Every window has a spectacular lake view Low fees, Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion , Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak, Spacious Country Home w/ Hot Tub, near Colby/Thomas, Lovely Home on Androscoggin Lake |
Top Locations for Holiday Homes in Oakland
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Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Pressey House Lakeside Bed & Breakfast

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

Classic and adorable Maine camp on North Pond in the Belgrade Lakes
More ways to explore Oakland
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^Subject to availability and chosen travel dates.