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

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston OR
The price is NZ$653 per night from 10 May to 11 May
NZ$653
10 May - 11 May
includes taxes & fees
Stay at this holiday home in Winston. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Abacela Winery and Wildlife Safari are located ...
Opens in a new windowThe Watusi Place - A Modern Umpqua Valley Getaway
River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty

River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty

Idleyld Park OR
Stay at this holiday home in Idleyld Park. Enjoy free Wi-Fi, patios and an in-room coffee maker. Popular attraction Little River is located nearby.
Opens in a new windowRiver Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty
Grove Stay

Grove Stay

Sutherlin OR
Stay at this holiday home in Sutherlin. Enjoy laundry facilities and air conditioning. Popular attractions Umpqua Golf Resort and Central Park are located ...
Opens in a new windowGrove Stay
Save an average of 15% on thousands of hotels when you're signed in
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water

Idleyld Park OR
Stay at this holiday home in Idleyld Park. Enjoy free Wi-Fi, patios and an in-room coffee maker. Popular attraction Little River is located nearby.
Opens in a new windowRiver Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!

Roseburg OR
The price is NZ$303 per night from 24 May to 25 May
NZ$303
24 May - 25 May
includes taxes & fees
Stay at this holiday home in Roseburg. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Douglas County Museum of History ...
Opens in a new windowDowntown Stay at the Red Tiny Twin!
Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg

Roseburg OR
Stay at this holiday home in Roseburg. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Umpqua Valley Tennis Center and Stewart Park are ...
Opens in a new windowRelax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg
Heavenly Bungalow, immaculately clean, close to downtown!

Heavenly Bungalow, immaculately clean, close to downtown!

Roseburg OR
Stay at this holiday home in Roseburg. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Stewart Park and Umpqua Valley Tennis Center are ...
Opens in a new windowHeavenly Bungalow, immaculately clean, close to downtown!
Home Sweet Home

Home Sweet Home

Sutherlin OR
Stay at this holiday home in Sutherlin. Enjoy free Wi-Fi, laundry facilities and air conditioning. Popular attractions Umpqua Golf Resort and Central Park are ...
Opens in a new windowHome Sweet Home
Below the Falls Lodge -  Next to Golden & Silver Falls

Below the Falls Lodge - Next to Golden & Silver Falls

Coos Bay OR
Stay at this holiday home in Coos Bay. Enjoy free Wi-Fi, a sauna and laundry facilities.
Opens in a new windowBelow the Falls Lodge - Next to Golden & Silver Falls
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.

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
59 Holiday Homes
Lowest Price
NZ$90
Highest Price
NZ$653
Popular accommodation
The Watusi Place - A Modern Umpqua Valley Getaway, River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty, Grove Stay, River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water, Downtown Stay at the Red Tiny Twin!, Relax & Rejuvenate in 4Br home with Hot Tub & Deck, in heart of Roseburg, Heavenly Bungalow, immaculately clean, close to downtown!, Home Sweet Home, Below the Falls Lodge - Next to Golden & Silver Falls

Top trending hotels in Oakland

Rice Hill Inn

Rice Hill Inn

2 out of 5
621 John Long Rd Oakland OR
Fully refundableReserve now, pay when you stay
The price is NZ$90 per night from 10 May to 11 May
NZ$90
10 May - 11 May
includes taxes & fees
Stay at this motel in Oakland. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. Popular attraction ...
Opens in a new windowRice Hill Inn
The Ranch Motel

The Ranch Motel

2 out of 5
581 John Long Rd Oakland OR
The price is NZ$166 per night from 10 May to 11 May
NZ$166
10 May - 11 May
includes taxes & fees
Stay at this motel in Oakland. Enjoy free Wi-Fi, free parking and a fireplace in reception. Our guests praise the helpful staff and the overall value in their ...
Opens in a new windowThe Ranch Motel
Great Outdoor Space! Serene Getaway in Oakland

Great Outdoor Space! Serene Getaway in Oakland

Oakland OR
Stay at this holiday home in Oakland. Enjoy patios, an in-room coffee maker and air conditioning. Popular attractions Oakland City Park and Central Park are ...
Opens in a new windowGreat Outdoor Space! Serene Getaway in Oakland
Save an average of 15% on thousands of hotels when you're signed in
Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

3 out of 5
Oakland OR
Stay at this business-friendly cottage in Oakland. Enjoy free parking, patios and in-room fireplaces. Popular attractions Oakland City Park and Central Park ...
Opens in a new windowSouthern Oregon Cabin: Fire Pit & Private Pond!
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.