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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Oakland vacation rentals

Terrace/patio

1. 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.
$111 nightly
The price is $112
Aug 7 - Aug 8
Total with taxes and fees
Lil Cedar Lodge
Exterior

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, (18 reviews)
"Great location, nice and quiet easy to get to fantastic hosts."
United States
Lee and Kristy D.
$138 nightly
The price is $140
Aug 10 - Aug 11
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
Terrace/patio

3. 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, (25 reviews)
"Beautiful property and incredible stay. Not only was the room clean, private and super comfortable, the hosts were amazing. They made my comfort a priority every day! Definitely would give it a 5 star rating, I will recommend it to family and friends."
United States
Betty W.
$254 nightly
The price is $278
Aug 8 - Aug 9
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior

4. <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, (111 reviews)
"We really enjoyed our stay at April’s house. It was a comfortable house and we loved being so close to Stewart Park for our daily walks."
United States
Sara W.
$193 nightly
The price is $211
Aug 10 - Aug 11
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Deluxe Apartment, City View | Private kitchen

5. Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
$361 nightly
The price is $395
Aug 19 - Aug 20
Total with taxes and fees
Bell Sister Flats
Dining

6. 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, (2 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
Exterior detail

7. Downtown Stay at the Blue Tiny Twin

Downtown Stay at the Blue Tiny Twin
Roseburg
9.6 out of 10, Exceptional, (21 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.
$160 nightly
The price is $175
Aug 15 - Aug 16
Total with taxes and fees
Downtown Stay at the Blue Tiny Twin
Dining

8. 4 BEDROOM House across from River in Best Roseburg area!

4 BEDROOM House across from River in Best Roseburg area!
Roseburg
10.0 out of 10, Exceptional, (30 reviews)
"Great stay as always"
United States
Anonymous traveler
$234 nightly
The price is $256
Aug 24 - Aug 25
Total with taxes and fees
4 BEDROOM House across from River in Best Roseburg area!
Exterior detail

9. 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, (30 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.
$182 nightly
The price is $199
Aug 23 - Aug 24
Total with taxes and fees
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior

10. 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, (42 reviews)
"Nice place, great location."
United States
Gordon
$211 nightly
The price is $231
Aug 19 - Aug 20
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Exterior

11. Downtown Stay at the Red Tiny Twin!

Downtown Stay at the Red Tiny Twin!
Roseburg
9.8 out of 10, Exceptional, (26 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.
$151 nightly
The price is $165
Aug 9 - Aug 10
Total with taxes and fees
Downtown Stay at the Red Tiny Twin!
Coffee/tea maker, fridge, microwave, oven

12. 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.
$329 nightly
The price is $360
Aug 13 - Aug 14
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Dining

13. The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (57 reviews)
"Good hosts & very nice home."
United States
Pamela M.
$357 nightly
The price is $387
Aug 10 - Aug 11
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior detail

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

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
$352 nightly
The price is $385
Aug 7 - Aug 8
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Coffee/tea maker, fridge, microwave, oven

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
9.6 out of 10, Exceptional, (33 reviews)
"Great little house. Had everything you needed. About a 20 min drive south of Eugene. Would book again if the need arose."
United States
Kevin
$306 nightly
The price is $344
Aug 31 - Sep 1
Total with taxes and fees
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Property grounds

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, (234 reviews)
"Great space — great for a large group!"
United States
Corey N.
$476 nightly
The price is $483
Sep 1 - Sep 2
Total with taxes and fees
Great Vintage 2500sq ft. country cabin amazing river front setting!
Interior

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, (212 reviews)
"The location is spectacular "
United States
John S.
$379 nightly
The price is $385
Sep 2 - Sep 3
Total with taxes and fees
Below the Falls Lodge - Next to Golden & Silver Falls
Private kitchen

18. The Little Pearl, Boutique Designer Cottage in Cottage Grove’s Historic District

The Little Pearl, Boutique Designer Cottage in Cottage Grove’s Historic District
Cottage Grove
$360 nightly
The price is $405
Sep 1 - Sep 2
Total with taxes and fees
The Little Pearl, Boutique Designer Cottage in Cottage Grove’s Historic District
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

10/10 Excellent
"This is our go to place when we visit Roseburg. The setting is beautiful and peaceful. The rooms are clean and comfortable with views of the river from the balcony. Staff is friendly and helpful"
Christina 1-night trip
Posted 4 hours ago
Riverfront Inn Roseburg

Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 vacation.

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 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?

Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews: This vacation home rental near Oakland is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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?

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 larger area, you’ll find MarshAnne Landing and Reustle Prayer Rock Vineyards.

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.