Oakland Vacations from $429

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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

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Creswell
Valley River Inn
Counting Z's
Graduate by Hilton Eugene
Driftwood Shores Resort And Conference Center
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Discover the most popular places to visit in Oakland

Oakland Hotel Deals

The Ranch Motel

The Ranch Motel

2 out of 5
581 John Long Rd Oakland OR
$68 nightly
The price is $70 total per night from Jan 27 to Jan 28
$70 total
Jan 27 - Jan 28
Total with taxes and fees
8.8/10 Excellent! (79 reviews)
A cool place to stay
The lady at the front desk was very nice. A unique place to stay, clean room, and easy parking.

Reviewed on Aug 7, 2025

The Ranch Motel
Rice Hill Inn

Rice Hill Inn

2 out of 5
621 John Long Rd Oakland OR
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $55 total per night from Jan 17 to Jan 18
$55 total
Jan 17 - Jan 18
Total with taxes and fees
7.6/10 Good! (232 reviews)
Very excellent stay

Reviewed on Dec 23, 2025

Rice Hill Inn
Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

3 out of 5
Oakland OR
Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there.

Reviewed on Oct 25, 2024

Southern Oregon Cabin: Fire Pit & Private Pond!
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.

Find the Best Oakland Vacation Packages

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.2°F (5.1°C)Light RainMostly CloudyAverageSlightly Low
February41.2°F (5.1°C)Light RainMostly CloudyAverageSlightly Low
March43.7°F (6.5°C)Light RainMostly CloudyAverageAverage
April47.7°F (8.7°C)Light RainMostly CloudySlightly HighAverage
May53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
June59.5°F (15.3°C)Light RainMostly SunnySlightly HighSlightly High
July65.7°F (18.7°C)No RainMostly SunnySlightly HighSlightly High
August66.2°F (19.0°C)No RainSunnyAverageSlightly High
September61.2°F (16.2°C)Light RainMostly SunnyAverageAverage
October52.9°F (11.6°C)Light RainMostly SunnySlightly LowAverage
November44.6°F (7.0°C)Light RainMostly CloudySlightly LowAverage
December39.6°F (4.2°C)Moderate RainMostly CloudySlightly LowSlightly Low

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.

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
940
Max Temp Winter
50ºF
Max Temp Summer
75ºF
Top Sights
Reustle Prayer Rock Vineyards, Becker Vineyard and Henry Estate Winery

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Frequently asked questions

How much does an Oakland vacation package cost?
You can pick up a vacation package to this destination from $429 on Expedia. However, how much your vacation to Oakland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Oakland?
If you'd like to score a cheap Oakland vacation package, consider planning a trip in January, March and December. You're likely to find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Oakland?
With a well-planned itinerary, you can easily tick off the main Oakland attractions in a few days. But if you prefer to discover hidden gems or go on day trips, consider booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Use Expedia's filter tool to help you find some of the best Oakland package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Oakland package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and stays separately. Better still, you can customize your Oakland escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Oakland?
If you've got your Oakland vacation dates finalized, book as soon as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
If you're like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Oakland vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.