Oskaloosa Vacations from $581
Book a Hotel + Flight or Car together to unlock savings
Your Oskaloosa Vacation
Lock in a Oskaloosa vacation package and prepare for a wonderful getaway. Known for its rich history and welcoming locals, there's tons to keep you on the move in this captivating city. Any trip to Oskaloosa needs a well-thought-out itinerary. Fill yours with major attractions like William Penn University, Southern Iowa Fair and Lake Keomah State Park. Don't delay your visit to this city any longer. The ultimate Oskaloosa vacation is just a few clicks away with Expedia.
The Latest Oskaloosa vacation packages
Price found within the past 48 hours. Click for updated prices.
Stoney Creek Hotel Des Moines - Johnston
$581
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Des Moines (DSM)
8.8/10 Excellent! (1,904 reviews)
Booked it for the outdoor pool. However, they rent out the pool to children's parties. 15 screaming kids invaded the pool and what was a relaxing afternoon ended abruptly.
Reviewed on Sep 28, 2026
Stay near popular Oskaloosa attractions
City Square Park
9.2/10 (79 reviews)
Oskaloosa's City Square Park features daily bandstand performances and seasonal events. Enjoy evening concerts with a blanket or visit during Art on the Square to experience Iowa's heartland culture at its finest.
William Penn University
8.6/10 (40 reviews)
Founded in 1873, William Penn University offers a liberal arts education rooted in Quaker traditions. Visitors can explore the historic campus with its blend of classic architecture and modern facilities.
Southern Iowa Fair
6.6/10 (10 reviews)
This historic fair, dating back to 1852, showcases Iowa's agricultural heritage through livestock exhibitions and competitions. Enjoy grandstand performances and authentic Midwestern fair foods during its mid-July run.
Lake Keomah State Park
Surrounded by 366 acres of woodlands, Lake Keomah State Park offers a serene escape with its 84-acre fishing lake. Follow the three-mile lakeside trail to spot blue herons while enjoying the tranquil natural setting.
Oskaloosa Public Library
This historic Carnegie library has served Oskaloosa since 1903 with its classic architecture and welcoming atmosphere. Browse collections across multiple floors or join community programs.
Edmundson Golf Course
7.2/10 (15 reviews)
This historic 18-hole public course features rolling fairways and undulating greens set among mature trees. Enjoy a challenging round with water hazards while taking advantage of the well-equipped practice facilities.
Nelson Pioneer Farm Museum
Step back in time at Nelson Pioneer Farm & Museum, where 22 historic buildings showcase rural Iowa life from 1850-1890. Explore the brick farmhouse, log cabin, and blacksmith shop while learning about settler traditions.
VanderWilt Park
7.6/10 (13 reviews)
VanderWilt Park offers two well-maintained little league fields where Oskaloosa's youth showcase their talents. Catch a spirited community game during baseball season while enjoying this local family-friendly space.
Oskaloosa Hotel Deals
EverSpring Inn & Suites
2401 A Ave West Oskaloosa IA
Fully refundableReserve now, pay when you stay
$73 nightly
$82 total
Sep 30 - Oct 1
Total with taxes and fees
Fairfield Inn & Suites by Marriott Oskaloosa
2325 COAL MINE LOOP Oskaloosa IA
Fully refundableReserve now, pay when you stay
$139 nightly
$156 total
Oct 18 - Oct 19
Total with taxes and fees
Quality Inn Oskaloosa
306 S 17th St Oskaloosa IA
Fully refundable
$61 nightly
$69 total
Oct 25 - Oct 26
Total with taxes and fees
7.8/10 Good! (499 reviews)
"This is an older hotel but dont judge a book by it's cover. The room was clean ( no carpet!)and just what we needed for a quick one night stay. The staff was nice. The only thing I could complain about was the washcloths were on the old side."
Reviewed on Sep 28, 2026
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 Oskaloosa Vacation Packages
Oskaloosa Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 11,600 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Tassel Ridge Winery, Lake Keomah State Park and William Penn University |
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Frequently asked questions
How much does an Oskaloosa vacation package cost?
Offering excellent value package deals from $581 on Expedia, you'll be surprised at how little a vacation to Oskaloosa costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oskaloosa?
If you'd like to score a cheap Oskaloosa vacation package, consider planning a trip in January, June and December. You'll generally find better rates on hotels and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Oskaloosa?
The ideal duration for your Oskaloosa vacation depends on what you'd like to do. Generally, a handful of days to a week will give you plenty of time to hit all the top attractions and explore some hidden gems along the way.
Is it worth booking a vacation package to Oskaloosa?
Oskaloosa is a good vacation destination with attractions like Southern Iowa Fair among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, an Oskaloosa vacation promises a good time for everyone.
How to find the best Oskaloosa package deals?
Start your search for an Oskaloosa package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Oskaloosa package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oskaloosa getaway off to a flying start.
Is it cheaper to book an Oskaloosa vacation as a package?
You can enjoy significant savings on your next Oskaloosa getaway by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Oskaloosa?
Secure fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Oskaloosa escape.
How to plan a trip to Oskaloosa?
- Pick your travel dates: What you plan to do in Oskaloosa and your preferred season will help you decide when to go.
- Budget wisely: As well as the price of your stay, you should consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Oskaloosa.
- Explore Oskaloosa with Expedia's trip planning tool: Gain insights into the leading attractions and best properties for your trip to Oskaloosa. You can also save your favorite places, collaborate with family and friends and manage your plans in one place.
- Decide how many days away: Start by compiling a list of the activities and attractions you want to experience in Oskaloosa. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the ideal Oskaloosa vacation package for you.
- Add on experiences and excursions: Have a look at our dedicated travel guide to find some exciting things to do in Oskaloosa in Oskaloosa. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Oskaloosa vacation packages?
Your Oskaloosa break should be an escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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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.