Photo by L Ru

Oakland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Oakland vacation rentals

Terrace/patio
Lil Cedar Lodge

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
The price is ￥13,415
￥17,598 total
includes taxes & fees
Jan 22 - Jan 23
Lil Cedar Lodge
Terrace/patio
A Restful Studio Near a Creek and Forest - Pets

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, (40 reviews)
"Amazing!!"
United Kingdom
Maureen S.
The price is ￥14,906
￥25,936 total
includes taxes & fees
Jan 28 - Jan 29
A Restful Studio Near a Creek and Forest - Pets
House (2 Bedrooms) | Interior
Hot Tub & Fenced Yard: Cozy Cottage Grove Home

Hot Tub & Fenced Yard: Cozy Cottage Grove Home

Hot Tub & Fenced Yard: Cozy Cottage Grove Home
3.0 star property
Cottage Grove
The price is ￥30,596
￥59,790 total
includes taxes & fees
Feb 9 - Feb 10
Hot Tub & Fenced Yard: Cozy Cottage Grove Home
Exterior
Tiny House nestled into the Forest on 160 acre Playground.

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 ￥18,075
￥24,717 total
includes taxes & fees
Jan 18 - Jan 19
Tiny House nestled into the Forest on 160 acre Playground.
Exterior
The Urban Boho Charmer with Private Backyard, BBQ & Hammock

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 ￥19,736
￥35,789 total
includes taxes & fees
Jan 17 - Jan 18
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
Living area
Home Sweet Home

Home Sweet Home

Home Sweet Home
Sutherlin
8.6 out of 10, Excellent, (10 reviews)
"We really enjoyed our stay! There are super comfortable beds, comfortable couch, fantastic washing machine, nice front porch and clean kitchen! The host was communicative and friendly ! Would for sure recommend and will stay there again on our next trip! "
United States
A T.
The price is ￥18,828
￥53,947 total
includes taxes & fees
Jan 12 - Jan 13
Home Sweet Home
Outdoor dining
Cozy 1-bedroom house in adorable Roseburg with AC

Cozy 1-bedroom house in adorable Roseburg with AC

Cozy 1-bedroom house in adorable Roseburg with AC
2.0 star property
Roseburg
The price is ￥13,263
￥29,565 total
includes taxes & fees
Jan 31 - Feb 1
Cozy 1-bedroom house in adorable Roseburg with AC
TV, books
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~

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 ￥17,259
￥30,925 total
includes taxes & fees
Jan 11 - Jan 12
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
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

Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Roseburg
9.6 out of 10, Exceptional, (52 reviews)
"It certainly is adorable, well-kept, well-stocked. We would love to stay here again!"
Canada
Faith S.
The price is ￥17,259
￥28,521 total
includes taxes & fees
Jan 22 - Jan 23
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
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

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 ￥18,757
￥48,374 total
includes taxes & fees
Jan 11 - Jan 12
Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun
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!

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 ￥30,439
￥38,141 total
includes taxes & fees
Jan 22 - Jan 23
Luxury, Full Service Bed and Breakfast - you are the only guest in our home!
Exterior detail
Downtown Stay at the Blue Tiny Twin

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.
The price is ￥15,000
￥28,528 total
includes taxes & fees
Feb 1 - Feb 2
Downtown Stay at the Blue Tiny Twin
Exterior detail
Downtown Stay at the Red Tiny Twin!

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 ￥15,000
￥28,528 total
includes taxes & fees
Feb 5 - Feb 6
Downtown Stay at the Red Tiny Twin!
Dining
The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (47 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 ￥23,300
￥57,286 total
includes taxes & fees
Jan 18 - Jan 19
The Watusi Place - A Modern Umpqua Valley Getaway
Exterior
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath

<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)
"Thank you so much for the comfy cozy place to stay! "
United States
Kristina C.
The price is ￥20,397
￥34,534 total
includes taxes & fees
Jan 22 - Jan 23
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
Property grounds
Great Vintage 2500sq ft. country cabin amazing river front setting!

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, (226 reviews)
"It was a nice big house by the river!"
United States
Stephen S.
The price is ￥23,526
￥53,847 total
includes taxes & fees
Feb 2 - Feb 3
Great Vintage 2500sq ft. country cabin amazing river front setting!
Deluxe Apartment, City View | Private kitchen
Bell Sister Flats

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is ￥41,625
￥57,682 total
includes taxes & fees
Jan 23 - Jan 24
Bell Sister Flats
Fridge, microwave, oven, stovetop
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
2.0 star property
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 ￥31,223
￥51,887 total
includes taxes & fees
Jan 11 - Jan 12
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Interior
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool

Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
Roseburg North
9.4 out of 10, Exceptional, (19 reviews)
"This property was very enjoyable for the children and I enjoyed the kitchen."
United States
Stacy B.
The price is ￥42,363
￥78,354 total
includes taxes & fees
Jan 18 - Jan 19
Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool
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

Lone Rock Guest House, 20 acres minutes from the North Umpqua River
2.0 star property
Glide
Lone Rock Guest House, 20 acres minutes from the North Umpqua River
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

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?


~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath: This vacation home near Oakland offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Oakland?

With 3 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. MarshAnne Landing and Misty Oaks Vineyard are other places to visit while you're in town.

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.