Oskaloosa Vacations from $683

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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.
Cozy Rest Motel

Cozy Rest Motel

2 out of 5
Indianola Hills
Price was $809, price is now $683 per person
$683
per person
Jan 29 - Feb 5
found 16 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Des Moines (DSM)
7.8/10 Good! (691 reviews)

Holiday Inn Downtown - Mercy Area by IHG

Holiday Inn Downtown - Mercy Area by IHG

3 out of 5
Downtown Des Moines
Price was $931, price is now $747 per person
$747
per person
Jan 29 - Feb 5
found 16 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Des Moines (DSM)
7.6/10 Good! (1,003 reviews)
Ac didn’t work in the building. 81 degrees was plenty hot. It wasn’t disclosed to us, we found out through others

Reviewed on Nov 6, 2026

Hyatt Place Altoona/Des Moines

Hyatt Place Altoona/Des Moines

3 out of 5
Price was $1,049, price is now $847 per person
$847
per person
Jan 29 - Feb 5
found 16 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Des Moines (DSM)
9.4/10 Exceptional! (939 reviews)

Hyatt Place Des Moines/Downtown

Hyatt Place Des Moines/Downtown

3 out of 5
Downtown Des Moines
Price was $973, price is now $806 per person
$806
per person
Jan 29 - Feb 5
found 16 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Des Moines (DSM)
8.2/10 Very Good! (1,006 reviews)
Great location downtown, reasonable room rate. The staff was very friendly and accomodating, particularly the young woman that was working the desk, the afternoon I checked in. She was outstanding. The breakfast was very good as well.

Reviewed on Nov 13, 2026

Hilton Des Moines Downtown

Hilton Des Moines Downtown

3.5 out of 5
Downtown Des Moines
Price was $1,544, price is now $1,317 per person
$1,317
per person
Jan 29 - Feb 5
found 16 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Des Moines (DSM)
9/10 Wonderful! (1,002 reviews)

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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.
See properties

Oskaloosa Hotel Deals

EverSpring Inn & Suites

EverSpring Inn & Suites

2.5 out of 5
2401 A Ave West Oskaloosa IA
$73 nightly
The price is $82 total per night from Nov 14 to Nov 15
$82 total
Nov 14 - Nov 15
Total with taxes and fees
8/10 Very Good! (770 reviews)
"Quiet"

Reviewed on Nov 11, 2026

EverSpring Inn & Suites
Quality Inn Oskaloosa

Quality Inn Oskaloosa

2.5 out of 5
306 S 17th St Oskaloosa IA
$53 nightly
The price is $59 total per night from Dec 13 to Dec 14
$59 total
Dec 13 - Dec 14
Total with taxes and fees
Quality Inn Oskaloosa
Budget Inn

Budget Inn

2 out of 5
1210 A Avenue East Oskaloosa IA
$65 nightly
The price is $73 total per night from Nov 14 to Nov 15
$73 total
Nov 14 - Nov 15
Total with taxes and fees
8.4/10 Very Good! (277 reviews)
"The service was great. But the air in one room the nob was broken and the hair dryer in the other room didn't even work."

Reviewed on Nov 2, 2026

Budget Inn
See all 101 properties in Oskaloosa
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 $683 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?

  1. Pick your travel dates: What you plan to do in Oskaloosa and your preferred season will help you decide when to go.
  2. 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.
  3. 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.
  4. 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.
  5. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the ideal Oskaloosa vacation package for you.
  6. 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.