Oskaloosa Vacations from $587

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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.
Holiday Inn Downtown - Mercy Area by IHG

Holiday Inn Downtown - Mercy Area by IHG

3 out of 5
Downtown Des Moines
Price was $728, price is now $587 per person
$587
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Des Moines (DSM)
7.8/10 Good! (1,015 reviews)
The parking lot was closed and parking was across the street. That long was not big enough to accommodate all the people staying at the hotel. Lots of kids staying at the hotel that were noisy late into the night

Reviewed on May 8, 2026

Hotel Fort Des Moines, Curio Collection by Hilton

Hotel Fort Des Moines, Curio Collection by Hilton

4.5 out of 5
Downtown Des Moines
Save 100% on your flight
Price was $1,260, price is now $908 per person
$908
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Des Moines (DSM)
9.6/10 Exceptional! (1,130 reviews)
We had a fantastic stay! The hotel’s lobby was beautiful, our room was sleek and comfortable and we were able to walk everywhere we wanted to go. I’d highly recommend it and would certainly stay again in the future!

Reviewed on May 13, 2026

Hampton Inn West Des Moines Lake Drive

Hampton Inn West Des Moines Lake Drive

3 out of 5
Price was $1,017, price is now $780 per person
$780
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Des Moines (DSM)
8.8/10 Excellent! (1,003 reviews)
Clean rooms but smaller than what I'm used to for a hampton. The staff could be more welcoming but then again I didn't have much interaction with them. The pool had no towels and the basket that had the dirty towels were overflowing. Would've been nice to have towels stocked for a weekend.

Reviewed on May 12, 2026

Hyatt Place West Des Moines Jordan Creek

Hyatt Place West Des Moines Jordan Creek

3 out of 5
Price was $996, price is now $767 per person
$767
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Des Moines (DSM)
9.2/10 Wonderful! (1,007 reviews)
Hyatt Place is always a desirable hotel for me when I travel. Clean comfortable rooms. Great amenities. The breakfast is always really good, too.

Reviewed on May 4, 2026

Baymont by Wyndham Des Moines Airport

Baymont by Wyndham Des Moines Airport

2.5 out of 5
Southwestern Hills
Price was $880, price is now $726 per person
$726
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Des Moines (DSM)
9.4/10 Exceptional! (1,166 reviews)
staff was so kind and made the process so easy, amazing price for the room

Reviewed on May 8, 2026

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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

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

VanderWilt Park

Explore the great outdoors at VanderWilt Park, a lovely green space in Oskaloosa. Make some time to visit the cathedral while you're in the area.

VanderWilt Park

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 May 17 to May 18
$89 total
May 17 - May 18
Total with taxes and fees
8.2/10 Very Good! (692 reviews)
Checked in at after 10:00 PM. We had to ask for hand soap for the bathroom & an ice bucket because they were not in the room. The bed had no top sheet. The breakfast was all picked over before 8 AM. No fruit or yogurt available. No healthy options.

Reviewed on May 13, 2026

EverSpring Inn & Suites
Fairfield Inn & Suites by Marriott Oskaloosa

Fairfield Inn & Suites by Marriott Oskaloosa

3 out of 5
2325 COAL MINE LOOP Oskaloosa IA
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $167 total per night from May 24 to May 25
$167 total
May 24 - May 25
Total with taxes and fees
9.4/10 Exceptional! (255 reviews)
Property was new and very nice. There was a place to eat within walking distance that was convenient. The person who checked us in was okay, but lacked friendliness and when both the TVs in the lobby did not work, she was unhelpful and did not make any effort to resolve the issue.

Reviewed on May 3, 2026

Fairfield Inn & Suites by Marriott Oskaloosa
Quality Inn Oskaloosa

Quality Inn Oskaloosa

2.5 out of 5
306 S 17th St Oskaloosa IA
Fully refundable
$59 nightly
The price is $67 total per night from Jun 7 to Jun 8
$67 total
Jun 7 - Jun 8
Total with taxes and fees
7.6/10 Good! (478 reviews)
Excellent staff. Had a television issue but it was addressed promptly. Nice safe hotel.

Reviewed on May 14, 2026

Quality Inn Oskaloosa
See all 102 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 $587 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.