Oakland Vacation Rentals

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In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Oakland vacation rentals

Deluxe Apartment, City View | Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
$368 nightly
The price is $403
Apr 18 - Apr 19
Total with taxes and fees
Bell Sister Flats
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.
$405 nightly
The price is $411
Apr 19 - Apr 20
Total with taxes and fees
Great Vintage 2500sq ft. country cabin amazing river front setting!
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.
$111 nightly
The price is $112
Apr 25 - Apr 26
Total with taxes and fees
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.
$164 nightly
The price is $185
Apr 20 - Apr 21
Total with taxes and fees
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 traveler
$280 nightly
The price is $315
Apr 27 - Apr 28
Total with taxes and fees
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
$345 nightly
The price is $350
Apr 17 - Apr 18
Total with taxes and fees
Private bungalow with AC in charming Roseburg
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.
$221 nightly
The price is $242
Apr 24 - Apr 25
Total with taxes and fees
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
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.
$288 nightly
The price is $316
Apr 20 - Apr 21
Total with taxes and fees
Modern Mid-Century Retreat with Stylish Amenities & Family-Friendly Comfort
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
$211 nightly
The price is $231
Apr 19 - Apr 20
Total with taxes and fees
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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.
$353 nightly
The price is $383
Apr 22 - Apr 23
Total with taxes and fees
The Watusi Place - A Modern Umpqua Valley Getaway
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.
$329 nightly
The price is $360
Apr 17 - Apr 18
Total with taxes and fees
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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.
$194 nightly
The price is $212
May 2 - May 3
Total with taxes and fees
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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.
$319 nightly
The price is $349
Apr 18 - Apr 19
Total with taxes and fees
Home Sweet Home
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)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
$205 nightly
The price is $224
Apr 23 - Apr 24
Total with taxes and fees
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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.
$180 nightly
The price is $180
Apr 25 - Apr 26
Total with taxes and fees
A Restful Studio Near a Creek and Forest - Pets
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.
$155 nightly
The price is $158
Apr 25 - Apr 26
Total with taxes and fees
Tiny House nestled into the Forest on 160 acre Playground.
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.
$165 nightly
The price is $181
Apr 26 - Apr 27
Total with taxes and fees
Downtown Stay at the Blue Tiny Twin
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.
$156 nightly
The price is $170
Apr 17 - Apr 18
Total with taxes and fees
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.
$181 nightly
The price is $198
Apr 22 - Apr 23
Total with taxes and fees
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Exterior detail

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
Apr 17 - Apr 18
Total with taxes and fees
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

The Lodge at Roseburg

The Lodge at Roseburg

10/10 Excellent
"Great location and friendly staff. "
Sara 2-night trip
Posted 3 hours ago
The Lodge at 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 $158 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.

Explore a world of travel with Expedia

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?

Tiny House nestled into the Forest on 160 acre Playground. : This vacation home rental near Oakland offers a patio, a barbecue grill, 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 vacation with amenities like a selection of books.

How many vacation rentals are there in Oakland?

With 4 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 Umpqua Golf Resort.

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.