Oskaloosa Vacations from $469

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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.
My Place Hotel - Ankeny/ Des Moines, IA

My Place Hotel - Ankeny/ Des Moines, IA

3 out of 5
Price was $550, price is now $469 per person
$469
per person
Mar 16 - Mar 21
found 10 hours ago
Roundtrip non-stop flight included
Knoxville (TYS) to Des Moines (DSM)
9/10 Wonderful! (758 reviews)
The guy that checked me in wasnt very friendly, but the lady at the desk in the morning was very nice.

Reviewed on Dec 20, 2025

Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
Downtown Des Moines
Price was $780, price is now $607 per person
$607
per person
Feb 11 - Feb 15
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Des Moines (DSM)
9.6/10 Exceptional! (1,037 reviews)
As always an excellent choice. Our room was gorgeous. Breakfast was fantastic. Christmas get away was better because of this hotel.

Reviewed on Dec 26, 2025

Hyatt Place West Des Moines Jordan Creek

Hyatt Place West Des Moines Jordan Creek

3 out of 5
Price was $657, price is now $554 per person
$554
per person
Feb 11 - Feb 15
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Des Moines (DSM)
9.2/10 Wonderful! (1,004 reviews)
Clean, quiet, and breakfast was prob 7/10.

Reviewed on Dec 24, 2025

Cobblestone Inn & Suites - Winterset, IA

Cobblestone Inn & Suites - Winterset, IA

2.5 out of 5
Price was $661, price is now $559 per person
$559
per person
Mar 16 - Mar 21
found 10 hours ago
Roundtrip non-stop flight included
Knoxville (TYS) to Des Moines (DSM)
9.2/10 Wonderful! (708 reviews)
We found a bug on our bed, it bite Russ.

Reviewed on Nov 5, 2025

Wildwood Lodge

Wildwood Lodge

3 out of 5
Price was $615, price is now $521 per person
$521
per person
Feb 11 - Feb 15
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Des Moines (DSM)
9.6/10 Exceptional! (1,194 reviews)
Staff was friendly. Room was nice. Breakfast was a little bland but not bad.

Reviewed on Dec 20, 2025

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Discover the most popular places to visit in Oskaloosa

Southern Iowa Fair

Enjoy an outing to Southern Iowa Fair during your stay in Oskaloosa. Make some time to visit the churches while you're in the area.

Southern Iowa Fair

City Square Park

After visiting City Square Park, make a plan to see the other sights and activities in Oskaloosa. Make some time to visit the churches while you're in the area.

City Square Park

Mahaska Health

Though Mahaska Health might be what brings you to town, perhaps you'll have a chance to explore more of Oskaloosa while you are here.

Mahaska Health

Oskaloosa Hotel Deals

EverSpring Inn & Suites

EverSpring Inn & Suites

2.5 out of 5
2401 A Ave West Oskaloosa IA
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $89 total per night from Jan 2 to Jan 3
$89 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8/10 Very Good! (656 reviews)
The room was very clean. It was nice having both a refrigerator and micro-wave in the room.

Reviewed on Dec 5, 2025

EverSpring Inn & Suites
Fairfield Inn & Suites by Marriott Oskaloosa

Fairfield Inn & Suites by Marriott Oskaloosa

2.5 out of 5
2325 COAL MINE LOOP Oskaloosa IA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $156 total per night from Dec 29 to Dec 30
$156 total
Dec 29 - Dec 30
Total with taxes and fees
9.2/10 Wonderful! (227 reviews)
The staff was extremely helpful and the room was very clean.

Reviewed on Dec 23, 2025

Fairfield Inn & Suites by Marriott Oskaloosa
Quality Inn Oskaloosa

Quality Inn Oskaloosa

2.5 out of 5
306 S 17th St Oskaloosa IA
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Jan 4 to Jan 5
$66 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.6/10 Good! (461 reviews)
Breakfast was a bit lacking, but rooms where clean

Reviewed on Dec 5, 2025

Quality Inn Oskaloosa
See all 100 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 $469 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.