Oakland Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Oakland holiday rentals

Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is HK$670
HK$878 total
includes taxes & fees
26 Apr - 27 Apr
Lil Cedar Lodge
Interior

Fully Equipped Studio - Laundry - 65” Samsung Smart TV - Off-Street Parking

Fully Equipped Studio - Laundry - 65” Samsung Smart TV - Off-Street Parking
Cottage Grove
10.0 out of 10, Exceptional, (22 reviews)
"Nice amenities, more than you normally see. Quiet and relaxing. Very nice accommodation."
United States
Stuart R.
The price is HK$775
HK$1,445 total
includes taxes & fees
22 Apr - 23 Apr
Fully Equipped Studio - Laundry - 65” Samsung Smart TV - Off-Street Parking
Fridge, microwave, oven, stovetop

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 HK$1,184
HK$2,407 total
includes taxes & fees
27 Apr - 28 Apr
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Exterior

Tiny House nestled into the Forest on 160 acre Playground.

Tiny House nestled into the Forest on 160 acre Playground.
Roseburg
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is HK$902
HK$1,234 total
includes taxes & fees
25 Apr - 26 Apr
Tiny House nestled into the Forest on 160 acre Playground.
Terrace/patio

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, (43 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is HK$862
HK$1,420 total
includes taxes & fees
3 May - 4 May
A Restful Studio Near a Creek and Forest - Pets
Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (51 reviews)
"Everything was great! "
United States
Candace L.
The price is HK$1,269
HK$3,034 total
includes taxes & fees
26 Apr - 27 Apr
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior detail

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 HK$744
HK$1,415 total
includes taxes & fees
23 Apr - 24 Apr
Downtown Stay at the Blue Tiny Twin
Exterior

<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, (94 reviews)
"Host was absolutely fantastic in assisting us with making sure our stay was perfect and peaceful we throughly enjoyed our stay the facilities were perfect for home cooked breakfast and a small family gathering to celebrate Christmas with our grandkids and kids Awill put as a favorite foe our next trip cant say thank you enough."
United States
Brenda L.
The price is HK$940
HK$1,655 total
includes taxes & fees
18 May - 19 May
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Exterior

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, (39 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$979
HK$1,792 total
includes taxes & fees
3 May - 4 May
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Property grounds

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 HK$1,480
HK$3,203 total
includes taxes & fees
26 Apr - 27 Apr
Great Vintage 2500sq ft. country cabin amazing river front setting!
Smart TV, fireplace, books, music library

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort

Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
Roseburg
9.8 out of 10, Exceptional, (39 reviews)
"As usual this property did not disappoint. Highly recommend! Beds are amazing. "
United States
Barry W.
The price is HK$1,057
HK$2,599 total
includes taxes & fees
29 Apr - 30 Apr
Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
Terrace/patio

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)
"Amazing B&B. Innkeepers James and Gail were exceptional hosts. Their attention to the details from arrival through departure made our stay very special. Breakfast was delicious. With its many thoughtful amnesties, this Inn has become one of our most memorable. It’s sophisticated, elegant and comfortable!"
United States
karen m.
The price is HK$1,519
HK$1,904 total
includes taxes & fees
24 Apr - 25 Apr
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Living area

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 HK$940
HK$2,744 total
includes taxes & fees
29 Apr - 30 Apr
Home Sweet Home
Exterior

Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (24 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 HK$670
HK$1,334 total
includes taxes & fees
22 Apr - 23 Apr
Downtown Stay at the Red Tiny Twin!
Exterior detail

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 HK$862
HK$1,544 total
includes taxes & fees
23 Apr - 24 Apr
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,174
HK$2,980 total
includes taxes & fees
2 May - 3 May
Bell Sister Flats
Smart TV

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, (54 reviews)
"Great place to stay with your pet. Was very well stocked."
United States
Melissa F.
The price is HK$1,175
HK$1,758 total
includes taxes & fees
23 Apr - 24 Apr
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is HK$2,373
HK$2,759 total
includes taxes & fees
22 Apr - 23 Apr
Private bungalow with AC in charming Roseburg
Room

Soothing 2-bedroom apartment with AC

Soothing 2-bedroom apartment with AC
Cottage Grove
Soothing 2-bedroom apartment with AC
Exterior detail

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is HK$1,872
HK$3,027 total
includes taxes & fees
24 Apr - 25 Apr
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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

Riverfront Inn Roseburg

Riverfront Inn Roseburg

8/10 Good
"Breakfast was cold tupe food, such as dry cereal and bagels, with no molk or cream cheese, or anything that needed to be kept cold. The lobby was open 24 hours, which i really appreciated and the staff were very friendly and very willing to help in any way. "
Cameron 3-night trip
Posted 6 hours ago
Riverfront Inn Roseburg

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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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?

Tiny House nestled into the Forest on 160 acre Playground. : This holiday home rental outside of Oakland offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an electric kettle and kitchenware. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Oakland?

With 4 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. In the wider area, you’ll find MarshAnne Landing and Umpqua Golf Resort.

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.