Oakland Holiday Rentals

  • 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
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Oakland holiday rentals

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 traveller
The price is HK$1,245
HK$2,536 total
includes taxes & fees
27 Mar - 28 Mar
Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews
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, (21 reviews)
"Nice amenities, more than you normally see. Quiet and relaxing. Very nice accommodation."
United States
Stuart R.
Fully Equipped Studio - Laundry - 65” Samsung Smart TV - Off-Street Parking
Terrace/patio

Lil Cedar Lodge

Lil Cedar Lodge
Roseburg
10.0 out of 10, Exceptional, (1 review)
The price is HK$669
HK$878 total
includes taxes & fees
27 Mar - 28 Mar
Lil Cedar Lodge
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.
The price is HK$860
HK$1,410 total
includes taxes & fees
8 Apr - 9 Apr
A Restful Studio Near a Creek and Forest - Pets
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.
The price is HK$743
HK$1,413 total
includes taxes & fees
26 Apr - 27 Apr
Downtown Stay at the Blue Tiny Twin
Exterior

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, (14 reviews)
"Wonderful environment and very peaceful stay. "
United States
Sarah C.
The price is HK$901
HK$1,232 total
includes taxes & fees
30 Mar - 31 Mar
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
Roseburg
9.6 out of 10, Exceptional, (39 reviews)
"Nice place, great location."
United States
Gordon
The price is HK$977
HK$1,755 total
includes taxes & fees
31 Mar - 1 Apr
The Urban Boho Charmer with Private Backyard, BBQ & Hammock
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, (92 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.
The price is HK$939
HK$1,637 total
includes taxes & fees
29 Mar - 30 Mar
<br>~Keasington House, a Mid Century Gem in Hucrest. 2bdrm, 2bath
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.
The price is HK$1,517
HK$1,832 total
includes taxes & fees
26 Apr - 27 Apr
Luxury, Full Service Bed and Breakfast - you are the only guest in our 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.
The price is HK$861
HK$1,423 total
includes taxes & fees
28 Mar - 29 Mar
Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital
Dining

The Watusi Place - A Modern Umpqua Valley Getaway

The Watusi Place - A Modern Umpqua Valley Getaway
Winston
10.0 out of 10, Exceptional, (50 reviews)
"Home was well stocked and was very accessible to our winery we belong to. "
United States
Amy W.
The price is HK$1,268
HK$2,981 total
includes taxes & fees
31 Mar - 1 Apr
The Watusi Place - A Modern Umpqua Valley Getaway
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.
The price is HK$1,166
HK$2,852 total
includes taxes & fees
30 Mar - 31 Mar
Great Vintage 2500sq ft. country cabin amazing river front setting!
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.
The price is HK$860
HK$1,541 total
includes taxes & fees
26 Apr - 27 Apr
Stunning Views~<br>Beulaire, a MCM Hillside Retreat Suite. <br>Beautiful Views~
Private kitchen

Bell Sister Flats

Bell Sister Flats
2.0 star property
Roseburg
The price is HK$2,096
HK$2,895 total
includes taxes & fees
26 Apr - 27 Apr
Bell Sister Flats
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.
The price is HK$669
HK$1,333 total
includes taxes & fees
30 Mar - 31 Mar
Downtown Stay at the Red Tiny Twin!
Outdoor dining

Private bungalow with AC in charming Roseburg

Private bungalow with AC in charming Roseburg
Roseburg
The price is HK$2,372
HK$2,757 total
includes taxes & fees
27 Mar - 28 Mar
Private bungalow with AC in charming Roseburg
Exterior detail

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants

Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
Roseburg
The price is HK$1,869
HK$2,962 total
includes taxes & fees
26 Apr - 27 Apr
Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants
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.
The price is HK$1,712
HK$2,757 total
includes taxes & fees
10 Apr - 11 Apr
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.
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

Best Western Garden Villa Inn

Best Western Garden Villa Inn

8/10 Good
"A very short stay, got in at 9pm and left at 8am. The room was small but clean and roomy enough. It had all the necessities although the little shampoo and conditioner bottles are really for one person. The bed had nice sheets and there was an extra blanket if needed. The bed was on the hard side though. The breakfast buffet was amazing and the staff was very friendly and kind. Only drawback is the hotel is in between 2 freeways and if it wasn’t for having earplugs , I would have had a hard time getting to sleep. Overall it’s a nice hotel for the price we paid and would stay again. "
Jadeen 1-night trip
Posted 7 hours ago
Best Western Garden Villa 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!

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Oakland has to offer?

Super clean Home, Hot Tub & Walk to Downtown Low FEES A+ Reviews: This holiday home rental outside of Oakland is located on a lake, and has a fireplace, a patio and a BBQ 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 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Oakland?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find MarshAnne Landing and Melrose Vineyards.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.