Oskaloosa Vacations from $344

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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.
Best Western Plus University Park Inn & Suites

Best Western Plus University Park Inn & Suites

2.5 out of 5
Price was $401, price is now $344 per person
$344
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Des Moines (DSM)
8.8/10 Excellent! (1,001 reviews)
This hotel never disappoints! I love the pillows and cozy bed!

Reviewed on Feb 1, 2026

Fairfield Inn and Suites by Marriott Des Moines West

Fairfield Inn and Suites by Marriott Des Moines West

2.5 out of 5
Price was $501, price is now $433 per person
$433
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Des Moines (DSM)
9/10 Wonderful! (1,002 reviews)
Everything about my day was wonderful! The room was clean. The staff was friendly. I was especially impressed with Judy who made my sisters and my stay absolutely unforgettable.

Reviewed on Feb 4, 2026

Hampton Inn West Des Moines Lake Drive

Hampton Inn West Des Moines Lake Drive

3 out of 5
Price was $625, price is now $544 per person
$544
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Des Moines (DSM)
9/10 Wonderful! (1,001 reviews)
Everything was wonderful. The breakfast was great with lots of options.

Reviewed on Jan 14, 2026

Hampton Inn Des Moines-Airport

Hampton Inn Des Moines-Airport

2.5 out of 5
Greater South Side
Price was $501, price is now $437 per person
$437
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Des Moines (DSM)
8.8/10 Excellent! (1,003 reviews)
Shuttle service was excellent

Reviewed on Feb 11, 2026

Kasa Downtown Des Moines

Kasa Downtown Des Moines

4 out of 5
Downtown Des Moines
Price was $480, price is now $420 per person
$420
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Des Moines (DSM)
9.2/10 Wonderful! (107 reviews)
Our stay in downtown Des Moines was for an entire week. This Kasa rental worked very well for us. It was nice having the extra things like kitchen, laundry, living room, game room, etc. that you don't get staying in a hotel. Our room was located in a noisy spot. We heard the garage doors open and close often. We were also awakened by the garage pickup. Still, it was a good value and great location for us.

Reviewed on Nov 19, 2025

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Discover the most popular places to visit in Oskaloosa

Multicolored spring tulips line a brick walkway towards the sundial and Tulip Toren Monument in Pella's Central Park at sunrise surrounded by crabapple trees, beds of tulips and flags flapping.

City Square Park

4.5/5(53 reviews)

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

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

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

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
$144 nightly
The price is $161 total per night from Feb 15 to Feb 16
$161 total
Feb 15 - Feb 16
Total with taxes and fees
9.2/10 Wonderful! (237 reviews)
The room was spotless. Breakfast was amazing.

Reviewed on Jan 26, 2026

Fairfield Inn & Suites by Marriott Oskaloosa
EverSpring Inn & Suites

EverSpring Inn & Suites

2.5 out of 5
2401 A Ave West Oskaloosa IA
8/10 Very Good! (664 reviews)
I didnt have any breakfast and disnt venture into the food area. Parking wa more than satisfactory. Sink in the bathroom eas clogged and filled with water at every use.

Reviewed on Jan 13, 2026

Get rates
EverSpring Inn & Suites
Quality Inn Oskaloosa

Quality Inn Oskaloosa

2.5 out of 5
306 S 17th St Oskaloosa IA
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $69 total per night from Feb 19 to Feb 20
$69 total
Feb 19 - Feb 20
Total with taxes and fees
7.6/10 Good! (468 reviews)
Rooms were super clean and staff were very pleasant and welcoming.

Reviewed on Jan 14, 2026

Quality Inn Oskaloosa
See all 111 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 $344 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.

Explore a world of travel with Expedia

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