Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

A Restful Studio Near a Creek and Forest - Pets

A Restful Studio Near a Creek and Forest - Pets
Roseburg
10.0 out of 10, Exceptional, (42 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is AU$237
includes taxes & fees
2 Feb - 3 Feb
A Restful Studio Near a Creek and Forest - Pets

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
9.6 out of 10, Exceptional, (29 reviews)
"Great place, well appointed, walk to all the fun stuff!"
United States
Anonymous traveller
The price is AU$461
includes taxes & fees
2 Feb - 3 Feb
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews

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

Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Roseburg
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely the most delightful and magical place to stay! Wonderfully gracious hosts! They made our honeymoon stay spectacular and special! James and Gail are fabulous. We had the most incredible breakfast as well. We felt like royalty! "
United States
Rachel S.
The price is AU$342
includes taxes & fees
1 Feb - 2 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!

The Urban Boho Charmer with Private Backyard, BBQ & Hammock

The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Roseburg
9.6 out of 10, Exceptional, (37 reviews)
"Nice place, great location."
United States
Gordon
The price is AU$328
includes taxes & fees
7 Feb - 8 Feb
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 reviews)
"This location worked great for our visit with family in the area. The house was clean and the beds were comfortable. Host was easy to work with - thanks!"
United States
Barbara S.
The price is AU$484
includes taxes & fees
7 Feb - 8 Feb
Home Sweet Home

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (48 reviews)
"The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place."
United States
Amy H.
The price is AU$528
includes taxes & fees
1 Feb - 2 Feb
The Watusi Place - A Modern Umpqua Valley Getaway

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is AU$162
includes taxes & fees
1 Feb - 2 Feb
Lil Cedar Lodge

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is AU$559
includes taxes & fees
10 Feb - 11 Feb
Bell Sister Flats

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.6 out of 10, Exceptional, (13 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is AU$226
includes taxes & fees
1 Feb - 2 Feb
Tiny House nestled into the Forest on 160 acre Playground.

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
9.8 out of 10, Exceptional, (39 reviews)
"We had a great stay while we visited family. The house had everything we needed, and the new mattresses were very comfortable. Gary was easy to get ahold of and responded quickly. We would stay again. "
United States
Riley E.
The price is AU$412
includes taxes & fees
2 Feb - 3 Feb
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun

Charming cottage studio in serene environment perfect for a relaxing getaway

Charming cottage studio in serene environment perfect for a relaxing getaway
Winston
The price is AU$265
includes taxes & fees
3 Mar - 4 Mar
Charming cottage studio in serene environment perfect for a relaxing getaway

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

Great Vintage 2500sq ft. country cabin amazing river front setting!
Scottsburg
9.6 out of 10, Exceptional, (227 reviews)
"It was a nice big house by the river!"
United States
Stephen S.
The price is AU$482
includes taxes & fees
2 Feb - 3 Feb
Great Vintage 2500sq ft. country cabin amazing river front setting!

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

<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Roseburg
9.8 out of 10, Exceptional, (91 reviews)
"Thank you so much for the comfy cozy place to stay! "
United States
Kristina C.
The price is AU$301
includes taxes & fees
28 Feb - 1 Mar
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.4 out of 10, Exceptional, (19 reviews)
"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."
United States
John L.
The price is AU$259
includes taxes & fees
1 Feb - 2 Feb
Downtown Stay at the Blue Tiny Twin

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

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Roseburg
9.6 out of 10, Exceptional, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is AU$259
includes taxes & fees
1 Feb - 2 Feb
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Roseburg
9.6 out of 10, Exceptional, (29 reviews)
"Finding the entry to the property was hardest part. Parking was OK. The views and the space was great. Nice central location for many places to visit."
United States
Nicole B.
The price is AU$282
includes taxes & fees
1 Feb - 2 Feb
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (21 reviews)
"It was a perfect place for us to stay for a short trip to visit family with our two little dogs."
United States
Rochelle S.
The price is AU$259
includes taxes & fees
5 Feb - 6 Feb
Downtown Stay at the Red Tiny Twin!

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!"
United States
CARISSA F.
The price is AU$510
includes taxes & fees
1 Feb - 2 Feb
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Glide
The price is AU$849
includes taxes & fees
20 Feb - 21 Feb
Lone Rock Guest House, 20 acres minutes from the North Umpqua River

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is AU$491
includes taxes & fees
1 Feb - 2 Feb
Private bungalow with AC in charming Roseburg
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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Top Oakland Hotel Reviews

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 favourite 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 depend 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 AU$226 per night. Entering your travel dates in the search wizard might find you 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?

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool: This holiday home rental outside of Oakland offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a patio and 1 hot tub.

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.