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

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

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

Cozy Long Pond Cottage: private mooring & shared dock

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

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

Cozy House in the heart of Waterville Maine.
![A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]](https://images.trvl-media.com/lodging/67000000/66870000/66866400/66866389/314004e9_y.jpg?impolicy=resizecrop&rw=340&ch=150)
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]

Classy AF Home Steps from Colby and Trails

Spectacular Location Reasonably Priced
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 | 131 Holiday Homes |
|---|---|
Lowest Price | NZ$399 |
Highest Price | NZ$477 |
Popular accommodation | Spacious Country Home w/ Hot Tub, near Colby/Thomas, Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly, Cozy Long Pond Cottage: private mooring & shared dock, Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting, Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion , Cozy House in the heart of Waterville Maine., A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible], Classy AF Home Steps from Colby and Trails, Spectacular Location Reasonably Priced |
Top trending hotels in Oakland

Sister A-Frame in Woods B

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Cozy Long Pond Cottage: private mooring & shared dock

Charming historic guest house on farm 3 bedrooms wood stove pet friendly
More ways to explore Oakland
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
