Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

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

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

Roseburg
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
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Roseburg
With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of Harvard Medical Park and South Umpqua River.
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
Indigo Collective - Modern Comfort & Bold Design

Indigo Collective - Modern Comfort & Bold Design

Roseburg
Located in Roseburg, this vacation home is within a 5-minute drive of Stewart Park and Harvard Medical Park.
Indigo Collective - Modern Comfort & Bold Design
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The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

Winston
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
Below the Falls Lodge -  Next to Golden & Silver Falls

Below the Falls Lodge - Next to Golden & Silver Falls

Coos Bay
With a stay at this vacation home in Coos Bay, you'll be on the waterfront, and 22.9 mi (36.8 km) from Coos Bay Boardwalk and 23.5 mi (37.8 km) from Mingus ...
Below the Falls Lodge - Next to Golden & Silver Falls
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Xenia House-Roseburg Retreat with a View! Near Wildlife Safari

Roseburg
With a stay at this vacation home in Roseburg, you'll be within a 10-minute drive of Wildlife Safari and Spangler Vineyards.
Xenia House-Roseburg Retreat with a View! Near Wildlife Safari
Family home

Family home

Roseburg
With a stay at this vacation home in Roseburg, you'll be within a 5-minute drive of South Umpqua River and Harvard Medical Park.
Family home
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
Located in Idleyld Park, this vacation home is on a river, within a 15-minute drive of North Umpqua River and Umpqua National Forest.
River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water
Family-Friendly Winston Vacation Rental w/ Deck!

Family-Friendly Winston Vacation Rental w/ Deck!

Winston
With a stay at this vacation home in Winston, you'll be within a 10-minute drive of Wildlife Safari and Abacela Winery.
Family-Friendly Winston Vacation Rental w/ Deck!
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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
58 Holiday Homes
Lowest Price
Highest Price
Popular accommodation

~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath, Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun, Indigo Collective - Modern Comfort & Bold Design, The Watusi Place - A Modern Umpqua Valley Getaway, Below the Falls Lodge - Next to Golden & Silver Falls, Xenia House-Roseburg Retreat with a View! Near Wildlife Safari, Family home, River Vista Homes: Perfect for Fishing, Swimming, and Relaxing by the Water, Family-Friendly Winston Vacation Rental w/ Deck!

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
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
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!

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!
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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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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.