Oakland Vacations from $416
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Your Oakland Vacation
Our vacation packages to Oakland let you create your own adventure. Tailor your journey to your needs and interests and make the most of your time in this lively city. Every trip to Oakland just has to include a bit of sightseeing. What to do first? Umpqua Golf Resort and MarshAnne Landing are main attractions. Don't delay your visit to this city any longer. Your ultimate Oakland vacation is just a few clicks away with Expedia.
The Latest Oakland Vacation Packages
- Motel 6 Albany, OR
Dec 7 - Dec 11Motel 6 Albany, OR + Flight
Albany4 nights2.0 star property6.6/10 - (59 reviews)Roundtrip • Los Angeles (LAX) - Eugene (EUG)LAX - PDX • Nonstop PDX - LAX • Nonstop$469$416found 1 day agoper traveler - Super 8 by Wyndham Albany/Corvallis
Jan 5 - Jan 9Super 8 by Wyndham Albany/Corvallis + Flight
Albany4 nights2.0 star property7.4/10 - Good (1,000 reviews)"Room was cold. It took an hour to warm up. Maintenance cart is very loud and starts rolling at 7am (change to soft rubber tires) Breakfast was standard Super8 quality."Reviewed November 3, 2026Roundtrip • Dallas (DFW) - Eugene (EUG)DFW - PDX • Nonstop PDX - DFW • Nonstop$552$490found 1 day agoper traveler - Holiday Inn Express Corvallis-On the River by IHG
Jan 5 - Jan 9Holiday Inn Express Corvallis-On the River by IHG + Flight
Corvallis4 nights2.5 star property9.0/10 - Wonderful (1,002 reviews)"One of the best rooms and places we stayed in for a while"Reviewed November 2, 2026Roundtrip • Dallas (DFW) - Eugene (EUG)DFW - PDX • Nonstop PDX - DFW • Nonstop$620$557found 1 day agoper traveler - Hayward Inn
Dec 23 - Dec 27Hayward Inn + Flight
East University4 nights3.0 star property9.0/10 - Wonderful (3,205 reviews)"Honestly this place is great, was looking for a hotel and this showed up. Great reviews and very budget friendly. We stayed 2 nights no complaints. Woke up to great selection of breakfast items. Would recommend this place to anyone!"Reviewed November 5, 2026Roundtrip • Austin (AUS) - Eugene (EUG)AUS - EUG • 1 stop EUG - AUS • 1 stop$891$809found 1 day agoper traveler - Downtown Inn
Dec 23 - Dec 27Downtown Inn + Flight
Downtown Eugene4 nights2.0 star property9.0/10 - Wonderful (900 reviews)Roundtrip • Austin (AUS) - Eugene (EUG)AUS - EUG • 1 stop EUG - AUS • 1 stop$926$842found 1 day agoper traveler
Where to stay in and around Oakland
Sutherlin
For families and outdoor enthusiasts looking for a memorable trip, Sutherlin offers a delightful blend of nature and adventure just about 2 miles by car from Oakland. Visitors can enjoy the scenic views at local landmarks like Central Park and Oakland City Park, while thrill-seekers will appreciate the recreational area and casino nearby. With its welcoming atmosphere and various activities, Sutherlin is a smart choice for those wanting an engaging and budget-friendly stay.
Rice Hill
Experience the charm of Rice Hill, an excellent hub for nature enthusiasts and budget travelers eager to explore the beauty of Oakland, Oregon. This quaint village offers easy access to attractions like Oakland City Park and Central Park, perfect for leisurely strolls, while the nearby Smith River invites outdoor adventure. With moderate visitor numbers throughout the year, Rice Hill provides a welcoming atmosphere. Nestled in Oakland, it’s a smart choice for those looking to immerse themselves in nature and enjoy a memorable stay.
Wilbur
If you are a nature lover or an adventure seeker, look no further than Wilbur, a charming village known for its stunning outdoor scenery and family-friendly atmosphere. Just about 10 miles by car from Oakland, Wilbur offers access to attractions like the Winchester Dam and nearby parks, perfect for enjoying a day outdoors. With consistent visitor numbers year-round and a focus on budget-friendly options, Wilbur is a smart choice for your next vacation stay.
Winchester
Immerse yourself in Winchester, where families and outdoor enthusiasts can easily access scenic spots like Winchester Dam, Stewart Park, and Discovery Garden. With its inviting nature and recreational opportunities, Winchester is perfect for a weekend getaway, offering a blend of relaxation and adventure. Located about 14 miles by car from Oakland, it serves as an ideal base to explore nearby lakes, rivers, and beaches. Choosing Winchester for your stay ensures a delightful blend of comfort and exploration.
Roseburg North
Travelers visiting the area often choose Roseburg North, especially families and budget-conscious adventurers seeking a blend of nature and excitement. This charming city offers easy access to stunning outdoor experiences, including the serene Winchester Dam and the expansive Stewart Park, perfect for picnics and play. The Douglas County Museum of History and Natural History provides enriching insights into the region's heritage. Located about 14 miles by car from Oakland, Roseburg North is a smart choice for your vacation stay.
Discover the most popular places to visit in Oakland
Oakland Hotel Deals
"The price is reasonable and it is very clean. The staff is nice and professional. They are also very good about accommodating their guests to the best of their abilities."
"Affordable"
"We usually stay at this hotel on our way down south And we find the staff is really good It is basic, but it is clean"
SureStay by Best Western Roseburg
SureStay by Best Western Roseburg
Find out more about Oakland
Things to do near Oakland
Oakland, Oregon, offers a charming blend of outdoor activities and scenic beauty, perfect for a romantic getaway. Visitors can explore educational attractions, relax at local resorts, and enjoy various recreational areas. Ideal for day trips, Oakland provides a range of activities that cater to nature lovers and adventure seekers alike, ensuring a memorable experience in this picturesque destination.
Shopping
In Oakland, explore local shops for unique gifts and souvenirs, including the charming downtown boutiques. If you're up for a drive, check out the nearby Roseburg Mall, about 20 miles away, featuring larger retail stores and a variety of dining options for a full shopping experience.
Recreation
Umpqua Golf Resort offers a scenic golfing experience just 3 miles from Oakland, perfect for sports enthusiasts. For those seeking culture and entertainment, Cottage Theatre, located 29 miles away, hosts captivating performances for families. Hidden Valley Golf Course, also 29 miles from Oakland, provides another great outdoor golfing option.
Adventure
The Umpqua Valley Tennis Center is an exhilarating destination located 14 miles from Oakland. With its vibrant atmosphere, you can enjoy a friendly game of tennis or hone your skills in a beautiful setting, making it a perfect spot for both relaxation and adventure.
Nightlife
Oakland's nightlife offers a cozy atmosphere with local pubs and bars. Visit the Oakland Tavern for friendly vibes and cold beers, or check out the local music scene at the nearby community center. Enjoy a laid-back evening filled with good company and entertainment in this charming town.
Find the best attractions in and around Oakland
Oakland, Oregon, is an ideal destination for outdoor enthusiasts and those seeking a romantic getaway. With attractions like urban parks, scenic rivers, and a dam, visitors can enjoy nature and city experiences alike. For family-friendly activities, consider exploring the Oakland Arena, the Oakland Zoo, and the Oakland Museum, all of which provide a glimpse into the vibrant local culture and outdoor beauty of this charming town.
- Oakland City Park: Enjoy a relaxing day at Oakland City Park, an urban oasis perfect for families. With its lush greenery, playgrounds, and picnic areas, it offers a vibrant atmosphere for outdoor activities and social gatherings, making it an ideal spot to unwind and connect with nature in the heart of the city.
- Winchester Dam: Located 10 miles from Oakland, Winchester Dam provides stunning scenic views that are perfect for photography enthusiasts and nature lovers alike. The serene environment surrounding the dam is perfect for a peaceful day of fishing or simply enjoying the tranquility of the water.
- Discovery Garden: Situated 13 miles from Oakland, Discovery Garden is a botanical paradise that fosters romance and exploration. Stroll through beautifully curated landscapes filled with diverse flora, making it an enchanting destination for families and couples looking to immerse themselves in nature's beauty.
Best time to go to Oakland
The best time to visit Oakland is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with moderate rain.
Tips to save on your trip to Oakland
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Oakland.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.
Frequently Asked Questions
What's the best vacation package for Oakland?
For couples seeking a romantic getaway, an Oakland vacation package can be built around a stay at The Ranch Motel, rated 8.5 out of 10. Located about 8 miles from central Oakland, this motel provides a comfortable base for exploring the scenic outdoor areas and vineyards like Misty Oaks Vineyard, about 14 miles away, that make Oakland a popular choice for romantic trips.
For travelers seeking the best value vacation packages in Oakland, consider a stay at Rice Hill Inn. Rated 7.8 out of 10, this inn is also about 8 miles from central Oakland and offers amenities like a 24-hour front desk and free WiFi. Travelers frequently praise its clean rooms and great location, making it a solid choice for an affordable Oakland vacation package.
How can I save money on a Oakland vacation package?
When you bundle, you can save up to 30%*. To save money on a Oakland package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Oakland?
Oakland, an outdoor and nature destination, offers a variety of activities for your Oakland vacation:
Browse and book things to do in Oakland on Expedia.
Do you need to rent a car in Oakland, or is public transport enough?
For an Oakland vacation package, renting a car is highly recommended for exploring this outdoor and nature destination. Oakland's attractions and natural sights are spread out, making a car essential for flexibility. You can easily reach places like Winchester Dam, about 11 miles from central Oakland, or Misty Oaks Vineyard, about 14 miles away.
The nearest major airport is Eugene, OR (EUG), about 40 miles from central Oakland, and a car provides the most direct access to your accommodation. A car offers the most convenient way to experience all that Oakland and its surroundings have to offer during your Oakland vacation packages with flights.
Are Oakland vacation package hotels conveniently located?
Oakland vacation package hotels are typically located a short drive from the town's central area, fitting its character as an outdoor and nature destination.
For example, The Ranch Motel, rated 8.5 out of 10, is about 8 miles from central Oakland. Similarly, Rice Hill Inn, rated 7.8 out of 10, also sits about 8 miles from central Oakland. This allows travelers to easily access both the town's amenities and the surrounding natural attractions during their Oakland vacation package.
Can I change or cancel my Oakland vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Oakland vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Oakland vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Oakland?
To find last-minute vacation packages to Oakland, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Oakland vacation packages?
Free cancellation on a Oakland vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Oakland vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Oakland getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Oakland vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.