Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
The price is AU$511 per night from 6 May to 7 May
AU$511
includes taxes & fees
6 May - 7 May
Located in Winston, this vacation home is in a rural location, within a 15-minute walk of Wildlife Safari and Abacela Winery.
The Watusi Place - A Modern Umpqua Valley Getaway
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Roseburg North
The price is AU$907 per night from 4 May to 5 May
AU$907
includes taxes & fees
4 May - 5 May
With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of North Umpqua River and Winchester Dam.
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets

Roseburg
The price is AU$262 per night from 8 May to 9 May
AU$262
includes taxes & fees
8 May - 9 May
This vacation home is 7.4 mi (11.9 km) from Little River and 10.6 mi (17.1 km) from North Umpqua River.
A Restful Studio Near a Creek and Forest - Pets
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<br>~Keasington House, a Mid Century Gem in Hucrest.  2bdrm, 2bath

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Roseburg
The price is AU$341 per night from 12 May to 13 May
AU$341
includes taxes & fees
12 May - 13 May
With a stay at this vacation home in Roseburg, you'll be a 5-minute walk from Umpqua Valley Tennis Center and 6 minutes by foot from Stewart Park.
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.

Roseburg
With a stay at this vacation home in Roseburg, you'll be within a 15-minute drive of Glaser Estate Winery & Distillery and North Umpqua River.
Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly.
River Vista Vacation Homes

River Vista Vacation Homes

3 out of 5
138 River Vista Court, Idleyld Park, OR
When you stay at River Vista Vacation Homes in Idleyld Park, you'll be on a river and within a 5-minute drive of North Umpqua River.
River Vista Vacation Homes
Lake Front bright home with office, wood stove and sauna

Lake Front bright home with office, wood stove and sauna

Cottage Grove
With a stay at this vacation home in Cottage Grove, you'll be within a 15-minute drive of Chambers Railroad Bridge and Lulu's Dog Park.
Lake Front bright home with office, wood stove and sauna
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Cottage Grove
The price is AU$655 per night from 16 May to 17 May
AU$655
includes taxes & fees
16 May - 17 May
A stay at this vacation home places you in the heart of Cottage Grove, within a 15-minute walk of Hidden Valley Golf Course and Lulu's Dog Park.
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Winston
Located in Winston, this vacation home is in a rural location, a 4-minute drive from South Umpqua River and 7 minutes from Spangler Vineyards.
Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen
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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
64 Holiday Homes
Lowest Price
AU$128
Highest Price
AU$907
Popular accommodation
The Watusi Place - A Modern Umpqua Valley Getaway, Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool, A Restful Studio Near a Creek and Forest - Pets,
~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath, Monroe River House. Jacuzzi. Private Beach. Prime Location. Family Friendly. , River Vista Vacation Homes, Lake Front bright home with office, wood stove and sauna, Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews, Large 7 bd 5 bath house. A few miles from wildlife safari. Gourmet kitchen

Top trending hotels in Oakland

The Ranch Motel by  OYO Oakland I-5

The Ranch Motel by OYO Oakland I-5

2 out of 5
581 John Long Rd, Oakland, OR
Fully refundable
The price is AU$146 per night from 16 May to 17 May
AU$146
includes taxes & fees
16 May - 17 May
Located in Oakland, The Ranch Motel by OYO Oakland I-5 is in a rural location, within a 15-minute drive of MarshAnne Landing and Oakland City Park.
The Ranch Motel by OYO Oakland I-5
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 AU$128 per night from 17 May to 18 May
AU$128
includes taxes & fees
17 May - 18 May
Located in Oakland, Rice Hill Inn is in a regional park, within a 15-minute drive of MarshAnne Landing and Oakland City Park.
Rice Hill Inn
Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

2 out of 5
Oakland
When you stay at this cabin in Oakland, you'll be on the waterfront, within a 5-minute drive of Oakland City Park and Central Park.
Southern Oregon Cabin: Fire Pit & Private Pond!
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Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

3 out of 5
Oakland
With a stay at this cottage in Oakland, you'll be within a 5-minute drive of Oakland City Park and Central Park.
Southern Oregon Cabin: Fire Pit & Private Pond!
Don't see what you're looking for?
See all available properties in Oakland
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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.

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^Subject to availability and chosen travel dates.