Photo by L Ru

Oakland Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Oakland

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

9.8 out of 10, Exceptional, (21)
"Very clean property with plenty of amenities. Very short walk to downtown shops and eating. One of the nicest properties that I have stayed at. Looking forward to staying here again if in the area."
The price is AU$501
includes taxes & fees
28 July - 29 July
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Charming Historic lodge #2

9.6 out of 10, Exceptional, (12)
"Wonderful hosts. "
The price is AU$190
includes taxes & fees
20 July - 21 July
Charming Historic lodge #2

Charming Historical lodge across from Umpqua river

9.6 out of 10, Exceptional, (27)
"Great overnight stop for our Crater Lake Visit. Easy check in and host was very friendly and proactive with communicaitons."
The price is AU$229
includes taxes & fees
20 July - 21 July
Charming Historical lodge across from Umpqua river

Historic Lodge across the street from the Umpqua River

9.6 out of 10, Exceptional, (27)
"Love this place, very accommodating, clean, and great owners! Will be booking with them again "
The price is AU$268
includes taxes & fees
24 July - 25 July
Historic Lodge across the street from the Umpqua River

A Restful Studio Near a Creek and Forest - Pets

10.0 out of 10, Exceptional, (33)
"Peaceful and clean."
The price is AU$284
includes taxes & fees
30 July - 31 July
A Restful Studio Near a Creek and Forest - Pets

Relaxing and peaceful cottage in rural area

10.0 out of 10, Exceptional, (14)
"It was a super quick stay, but the location was close to everything and we were very comfortable. "
The price is AU$353
includes taxes & fees
25 July - 26 July
Relaxing and peaceful cottage in rural area

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.8 out of 10, Exceptional, (7)
The price is AU$881
includes taxes & fees
30 July - 31 July
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.6 out of 10, Exceptional, (17)
"Inviting and comfortable "
The price is AU$271
includes taxes & fees
28 July - 29 July
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

10.0 out of 10, Exceptional, (22)
"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"
The price is AU$479
includes taxes & fees
29 July - 30 July
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

10.0 out of 10, Exceptional, (42)
"Bill's house was comfortable, and the house and property were consistent with the listing. The house and furnishings worked well for my family for our one-night stay."
The price is AU$361
includes taxes & fees
25 July - 26 July
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (25)
"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"
The price is AU$338
includes taxes & fees
23 July - 24 July
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

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

9.8 out of 10, Exceptional, (79)
"Love this little abode and recommend "
The price is AU$340
includes taxes & fees
21 July - 22 July
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (8)
"Stayed here for one evening while touring wineries in the region. Fantastic location, great communication from hosts, and a delightful property. Would recommend! "
The price is AU$245
includes taxes & fees
22 July - 23 July
Tiny House nestled into the Forest on 160 acre Playground.

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (38)
"We stayed here for a night since we had a nearby disc golf tournament. Leah was a great host and the house was super clean and comfy. Quiet neighborhood, cool back porch to hang out. Highly recommend! Thank you Leah!"
The price is AU$536
includes taxes & fees
21 July - 22 July
The Watusi Place - A Modern Umpqua Valley Getaway
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakland Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay. Oakland is known for its wineries and restaurants. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Oakland has to offer?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
: This holiday home rental outside of Oakland offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Oakland?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

While exploring the area, visit family-friendly sights like Douglas County Museum of History and Natural History, or get outside and enjoy nature at Umpqua River. MarshAnne Landing and Misty Oaks Vineyard are other places to visit while you're in town.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.