A waterfall surrounded by dense forest.

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Oakland vacation rentals

A living room with a sofa, a coffee table, a fireplace, a TV, and a painting on the wall.

1. Home Sweet Home

Home Sweet Home
Sutherlin
9.0 out of 10, Wonderful, (12 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 ￥18,919
￥55,244 total
includes taxes & fees
Nov 5 - Nov 6
Home Sweet Home
A wooden cabin named 'Lil Cedar Lodge' with a metal roof, two windows, and a small porch with a chair and table.

2. Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place. Really enjoyed my stay."
United States
Zakary S.
The price is ￥13,480
￥17,683 total
includes taxes & fees
Nov 12 - Nov 13
Lil Cedar Lodge
A wooden cabin with a deck, outdoor seating, and a pathway lit by ground lights.

3. 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 :)"
United States
kimberley
The price is ￥14,331
￥19,346 total
includes taxes & fees
Nov 4 - Nov 5
Tiny House nestled into the Forest on 160 acre Playground.
A modern house with a stone pathway leading to the entrance, surrounded by various plants and a large planter.

4. 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."
United States
Nicole B.
The price is ￥17,343
￥29,868 total
includes taxes & fees
Nov 5 - Nov 6
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
A house with a covered porch, a seating area with a sofa and armchair, and a small table.

5. <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, (118 reviews)
"Great stay, very clean. Would stay here again."
United States
Cindan G.
The price is ￥18,919
￥33,665 total
includes taxes & fees
Nov 30 - Dec 1
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
A small, single-story house with a green door, white trim, and a small porch.

6. 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, (45 reviews)
"Everything was great with the property! My daughter and I enjoyed our stay so much. When we have occasion to return to Roseburg we will look for this place first. I only marked “communication” as 3 stars because I didn’t have the need to communicate with the host. Lovely little house and quiet neighborhood."
United States
Norma B.
The price is ￥19,708
￥36,601 total
includes taxes & fees
Nov 30 - Dec 1
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
A small house with a porch and string lights.

7. 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!"
United States
Sue S.
The price is ￥12,770
￥24,688 total
includes taxes & fees
Nov 5 - Nov 6
Downtown Stay at the Red Tiny Twin!
A serene outdoor seating area with string lights, overlooking a body of water and a mountainous backdrop.

8. Private Umpqua River Retreat w/ 2 King Suites & Patio

Private Umpqua River Retreat w/ 2 King Suites & Patio
Roseburg
10.0 out of 10, Exceptional, (8 reviews)
"Great property with wonderful views and a quiet relaxing back patio. Large kitchen with a good refrigerator. Very comfortable beds."
United States
Laura O.
Private Umpqua River Retreat w/ 2 King Suites & Patio
A wooden deck with a white railing, a potted plant, and a table.

9. 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...
United States
Susan
The price is ￥28,872
￥36,107 total
includes taxes & fees
Nov 9 - Nov 10
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

10. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful flat! We loved our time there"
United States
Daniel
The price is ￥49,720
￥66,528 total
includes taxes & fees
Nov 5 - Nov 6
Bell Sister Flats
A modern kitchen with stainless steel appliances, a wooden dining table, and a tufted ottoman.

11. 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)
"Bell Sister Flats is amazing - so gorgeous, warm and inviting. We loved being on Main Street and walking to coffee, dinner, drinks. So much attention to detail and such comfort provided from the bed to the sheets to the towels and love seat and, oh the shower! Terry and Paul were wonderful hosts, so attentive and generous. Loved that they promoted the local community with goods and services in the flat. Loved our stay!"
United States
Tara T.
The price is ￥34,528
￥54,210 total
includes taxes & fees
Nov 5 - Nov 6
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
A modern house with a gravel driveway, large windows, and a view of a forest.

12. 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
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."
United States
Secret L.
The price is ￥50,960
￥94,962 total
includes taxes & fees
Oct 31 - Nov 1
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
A spacious living area with a wooden dining table, black chairs, a ceiling fan, and a television displaying a beach scene.

13. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (60 reviews)
"Great place for us and the kids after a long day at the wildlife safari!"
United States
Jessica M.
The price is ￥25,541
￥60,728 total
includes taxes & fees
Nov 1 - Nov 2
The Watusi Place - A Modern Umpqua Valley Getaway
A modern hotel room with a large bed, a sofa, a fireplace, and a TV mounted on the wall.

14. Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is ￥37,681
￥58,008 total
includes taxes & fees
Nov 5 - Nov 6
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Private kitchen

15. 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
9.8 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!"
United States
Joelle
The price is ￥26,837
￥53,088 total
includes taxes & fees
Nov 2 - Nov 3
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
A wooden deck with a view of a lake and forest.

16. 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, (239 reviews)
"such a great place, had everything we needed and plenty of room will definitely be staying again"
United States
Tami L.
The price is ￥47,140
￥84,813 total
includes taxes & fees
Nov 30 - Dec 1
Great Vintage 2500sq ft. country cabin amazing river front setting!
A tent with a skylight, wooden beams, and a window overlooking a forest.

17. Below the Falls Lodge - Next to Golden & Silver Falls

Below the Falls Lodge - Next to Golden & Silver Falls
Coos Bay
9.8 out of 10, Exceptional, (225 reviews)
"Great place to stay!"
United States
Paul C.
The price is ￥39,048
￥58,211 total
includes taxes & fees
Nov 1 - Nov 2
Below the Falls Lodge - Next to Golden & Silver Falls
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

Cottage Grove Inn

Cottage Grove Inn

10/10 Excellent
"Super place Wonderful staff"
kenyon 1-night trip
Posted 2 hours ago
Cottage Grove Inn

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!

Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, we offer vacation rentals close to top sights in Oakland, or you can choose a secluded option if you'd like a relaxing place to 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's the top vacation rental in Oakland?

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

How many vacation rentals are there in Oakland?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

Umpqua River and Tyee Mountain are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find MarshAnne Landing and Little River.

What’s a vacation rental in Oakland like?

Vacation rentals are private properties you can stay in for short or long periods in Oakland. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.