Photo by L Ru

Oakland Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    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

In two weeks
In one month
In two months
In three months

Holiday Rentals in Oakland

Our top choices for Oakland holiday rentals

Southern Oregon Cabin: Fire Pit & Private Pond!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
Southern Oregon Cabin: Fire Pit & Private Pond!

Romantic Vineyard Getaway in Oakland: Mtn Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was well organized with all the necessities/amenities that made our stay that much more comfortable. Perhaps instructions on how to operate front door lock would be helpful. Otherwise, everything else was perfect. Thank you! "
Romantic Vineyard Getaway in Oakland: Mtn Views!

Vineyard Farmhouse in Oakland w/ Hot Tub!

3.0 star property
Vineyard Farmhouse in Oakland w/ Hot Tub!

Two Story Victorian Farm House. Hot Tub!

10.0 out of 10, Exceptional, (6)
"We loved this house! The little extras made all the difference! It was spotless, toiletries were stocked in the bathrooms, the kitchen was gorgeous and easy to cook in and our teens were beyond thrilled with all the snacks. It was the perfect place for a couple lazy days after Christmas. The hot tub was wonderful (including the big fluffy towels) and it was only a couple block walk to the cute little downtown area. We fully enjoyed our stay. The hosts were responsive and kind about any questions...
Two Story Victorian Farm House. Hot Tub!

River Vista Vacation Homes

3.0 star property
9.2 out of 10, Wonderful, (45)
"The place was right on the river which was beautiful and it had everything that we would need. It was clean and pretty roomy for my family and I to spend the weekend there and we absolutely loved it! We’re already trying to make another trip out here!"
River Vista Vacation Homes

Great Vintage 2500sq ft. country cabin amazing river front setting!

9.6 out of 10, Exceptional, (221)
"Private, views are incredible and perfectly situated. "
The price is NZ$620
includes taxes & fees
1 Oct - 2 Oct
Great Vintage 2500sq ft. country cabin amazing river front setting!

Below the Falls Lodge - Next to Golden & Silver Falls

9.8 out of 10, Exceptional, (195)
"So peaceful. I would stay here again in a heartbeat. I wouldn’t change a thing. Worth the time to go see the falls. "
Below the Falls Lodge - Next to Golden & Silver Falls

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

9.6 out of 10, Exceptional, (31)
"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 NZ$369
includes taxes & fees
5 Sept - 6 Sept
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

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

9.8 out of 10, Exceptional, (45)
"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 NZ$352
includes taxes & fees
7 Sept - 8 Sept
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Red Tiny Twins, Downtown Eco & Pet Friendly Stay

9.8 out of 10, Exceptional, (14)
"Enjoyed the accommodations. just as advertised would stay again."
The price is NZ$296
includes taxes & fees
7 Sept - 8 Sept
Red Tiny Twins, Downtown Eco & Pet Friendly Stay

Firewater Lodge Cabin Experience

10.0 out of 10, Exceptional, (61)
"This place was amazing and we will be going back for sure. Peaceful and relaxing setting. Home is beautiful and has everything you will need. "
Firewater Lodge Cabin Experience

The Watusi Place - A Modern Umpqua Valley Getaway

10.0 out of 10, Exceptional, (45)
"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 NZ$660
includes taxes & fees
7 Sept - 8 Sept
The Watusi Place - A Modern Umpqua Valley Getaway

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

9.8 out of 10, Exceptional, (24)
"Very clean and very well furnished/equipped. Everything you could need (and more) for a comfortable stay. Great location walking distance to the historic section of town and restaurants."
The price is NZ$549
includes taxes & fees
15 Sept - 16 Sept
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

Tiny House nestled into the Forest on 160 acre Playground.

9.4 out of 10, Exceptional, (9)
"It was such a nice little spot to get away."
The price is NZ$268
includes taxes & fees
6 Sept - 7 Sept
Tiny House nestled into the Forest on 160 acre Playground.

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

9.8 out of 10, Exceptional, (83)
"April answered all my emails immediately and was very nice. Loved the location."
The price is NZ$367
includes taxes & fees
10 Sept - 11 Sept
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Lil Cedar Lodge

The price is NZ$191
includes taxes & fees
7 Sept - 8 Sept
Lil Cedar Lodge

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

9.6 out of 10, Exceptional, (15)
"This is the second time staying at this property and it is so peaceful. It's right on the river and is close to many trails and waterfalls. I highly recommend!"
River Vista Homes: Enjoy Swimming, Fishing, and Relaxation in Nature's Beauty

Family home

9.6 out of 10, Exceptional, (4)
"I would suggest to everyone to stay here!"
Family home

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

9.2 out of 10, Wonderful, (10)
"great property"
The price is NZ$909
includes taxes & fees
5 Sept - 6 Sept
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins

9.4 out of 10, Exceptional, (19)
"Just the right size and location for a wine country getaway weekend. Had everything we needed, and more. Will not hesitate to book again next trip, if it's available."
The price is NZ$287
includes taxes & fees
14 Sept - 15 Sept
Blue Downtown Stay ~ Eco & Pet Friendly Tiny Twins
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

Find out more about Oakland

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as NZ$191 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

The Watusi Place - A Modern Umpqua Valley Getaway: This holiday home rental outside of Oakland is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.