Oakland Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Oakland holiday rentals

Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,267
HK$3,082 total
includes taxes & fees
10 Feb - 11 Feb
Bell Sister Flats
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, (42 reviews)
"Enjoyed our stay!"
United States
Dana M.
The price is HK$742
HK$1,292 total
includes taxes & fees
23 Feb - 24 Feb
A Restful Studio Near a Creek and Forest - Pets
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)
"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 HK$1,516
HK$1,865 total
includes taxes & fees
8 Feb - 9 Feb
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is HK$668
HK$876 total
includes taxes & fees
8 Feb - 9 Feb
Lil Cedar Lodge
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, (37 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$977
HK$1,754 total
includes taxes & fees
8 Feb - 9 Feb
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

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 HK$900
HK$1,231 total
includes taxes & fees
9 Feb - 10 Feb
Tiny House nestled into the Forest on 160 acre Playground.
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$1,242
HK$2,488 total
includes taxes & fees
10 Feb - 11 Feb
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
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, (91 reviews)
"We had a great stay! The house was amazing, and peaceful. We would definitely stay again. "
United States
Ashley D.
The price is HK$938
HK$1,626 total
includes taxes & fees
8 Feb - 9 Feb
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Fridge, microwave, oven, stovetop

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 HK$1,711
HK$2,755 total
includes taxes & fees
8 Feb - 9 Feb
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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.
Downtown Stay at the Blue Tiny Twin
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is HK$2,367
HK$2,752 total
includes taxes & fees
8 Feb - 9 Feb
Private bungalow with AC in charming Roseburg
Exterior

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 HK$2,524
HK$4,679 total
includes taxes & fees
20 Feb - 21 Feb
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
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$1,164
HK$2,617 total
includes taxes & fees
9 Feb - 10 Feb
Great Vintage 2500sq ft. country cabin amazing river front setting!
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, (53 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is HK$859
HK$1,412 total
includes taxes & fees
8 Feb - 9 Feb
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Dining

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 HK$1,250
HK$1,427 total
includes taxes & fees
13 Feb - 14 Feb
Charming cottage studio in serene environment perfect for a relaxing getaway
Smart TV, fireplace, books, music library

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 HK$752
HK$2,175 total
includes taxes & fees
9 Feb - 10 Feb
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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$938
HK$2,704 total
includes taxes & fees
19 Feb - 20 Feb
Home Sweet Home
Dining

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 HK$1,160
HK$2,802 total
includes taxes & fees
10 Feb - 11 Feb
The Watusi Place - A Modern Umpqua Valley Getaway
Fridge, microwave, oven, stovetop

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 HK$742
HK$1,412 total
includes taxes & fees
8 Feb - 9 Feb
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$859
HK$1,540 total
includes taxes & fees
9 Feb - 10 Feb
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
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

Motel 6 Roseburg, OR

Motel 6 Roseburg, OR

10/10 Excellent
"Yes it was perfect"
Matthew 2-night trip
Posted 6 days ago
Motel 6 Roseburg, OR

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!

Explore a world of travel with Expedia

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?

Below the Falls Lodge - Next to Golden & Silver Falls: This holiday home rental outside of Oakland is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.