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Our top choices for Oakland vacation homes
1. Home Sweet Home
Home Sweet HomeSutherlin
8.8 out of 10, Excellent, (13 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!"
Barbara S.
The price is ￥19,002
￥50,284 total
includes taxes & fees
Nov 6 - Nov 7
2. 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, (21 reviews)
"My friend and I had an amazing stay. We went for a walk, had dinner out on the deck and finished the night drinking wine in the double swing. The stars were amazing. Listen to the owls as we went to sleep. Great place for a get away from the city lights :)"
kimberley
The price is ￥14,835
￥18,596 total
includes taxes & fees
Nov 9 - Nov 10
3. 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, (33 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."
Nicole B.
The price is ￥17,419
￥29,998 total
includes taxes & fees
Nov 16 - Nov 17
4. <br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bathRoseburg
9.8 out of 10, Exceptional, (120 reviews)
"Great stay, very clean. Would stay here again."
Cindan G.
The price is ￥19,002
￥31,732 total
includes taxes & fees
Nov 8 - Nov 9
5. The Urban Boho Charmer with Private Backyard, BBQ & Hammock
The Urban Boho Charmer with Private Backyard, BBQ & HammockRoseburg
9.6 out of 10, Exceptional, (45 reviews)
"Nice place, great location."
Gordon
The price is ￥19,794
￥34,680 total
includes taxes & fees
Nov 13 - Nov 14
6. Downtown Stay at the Red Tiny Twin!
Downtown Stay at the Red Tiny Twin!Roseburg
9.8 out of 10, Exceptional, (31 reviews)
"Close to downtown, well appointed, clean and comfortable. Thanks for a lovely stay!"
Sue S.
The price is ￥12,826
￥24,796 total
includes taxes & fees
Nov 7 - Nov 8
7. 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, (28 reviews)
"Our hosts, James and Gail, are so lovely. They really care about their guests experience and I felt they truly cared about our experience. It’s a gorgeous home that they have decorated meticulously, and made so comfortable for guests to enjoy. The bed was super comfy and the room cozy. The bedding and towels were soft and top notch. They didn’t skimp on anything. Gail is a great cook and provided homemade food, snacks, and drinks. Some items came from her garden. James is a master with sound and...
Susan
The price is ￥28,978
￥34,506 total
includes taxes & fees
Nov 9 - Nov 10
8. Lone Rock Guest House, 20 acres minutes from the North Umpqua River
Lone Rock Guest House, 20 acres minutes from the North Umpqua RiverGlide
10.0 out of 10, Exceptional, (2 reviews)
"I have stayed at probably 100 rental houses in my life - this is hands down my favorite and was best suited for my outdoor boys. There are endless things to do on the property and you are in the center of an outdoor adventure town with lakes, rivers, hikes, waterfalls, fishing and more. It was private, clean, well stocked, comfortable and high quality - and the host was responsive, welcoming and helpful. Thank you for the memories. I hope we can come back for an even longer stay next time."
Secret L.
The price is ￥51,147
￥90,489 total
includes taxes & fees
Nov 11 - Nov 12
9. The Watusi Place - A Modern Umpqua Valley Getaway
The Watusi Place - A Modern Umpqua Valley GetawayWinston
10.0 out of 10, Exceptional, (60 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
Jessica M.
The price is ￥25,675
￥58,295 total
includes taxes & fees
Nov 6 - Nov 7
10. Below the Falls Lodge - Next to Golden & Silver Falls
Below the Falls Lodge - Next to Golden & Silver FallsCoos Bay
9.8 out of 10, Exceptional, (225 reviews)
"Great place to stay!"
Paul C.
The price is ￥39,226
￥58,476 total
includes taxes & fees
Nov 8 - Nov 9
11. Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ ReviewsCottage Grove
9.8 out of 10, Exceptional, (40 reviews)
"This place was absolute perfection. Everything was user friendly thanks to this incredible host! All of the labels and instructions took away all of the what ifs and worries. We already can’t wait to stay here again! This house was the best part of our whole trip!"
Joelle
The price is ￥26,959
￥49,051 total
includes taxes & fees
Nov 6 - Nov 7
12. Private Umpqua River Retreat w/ 2 King Suites & Patio
Private Umpqua River Retreat w/ 2 King Suites & PatioRoseburg
10.0 out of 10, Exceptional, (9 reviews)
"Great property with wonderful views and a quiet relaxing back patio. Large kitchen with a good refrigerator. Very comfortable beds."
Laura O.
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.
Learn more about Oakland
This historic small town showcases beautifully preserved 19th-century buildings along its walkable main street. Visit Oakland Museum to explore pioneer artifacts, then enjoy wine tasting at nearby Umpqua Valley vineyards.
Top reviews in Oakland
Best Western Plus Hartford Lodge
Best Western Plus Hartford LodgeSutherlin
10/10 Excellent
Check in was fast and easy. Our breakfast was delicious. They have a cook on site and he made our breakfast. YUMMY!! You gotta stay just to try his cooking!!! We will be back
Theresa
