Book Holiday Homes in Oskaloosa

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Featured Holiday Homes in Oskaloosa

Charming, modern and cozy retreat on the bike path

Charming, modern and cozy retreat on the bike path

Pella
With a stay at this vacation home in Pella, you'll be a 4-minute walk from Central College and within a 5-minute drive of Molengracht Plaza.
Charming, modern and cozy retreat on the bike path
Charming 2-bedroom NEW house with WiFi, AC Pella/Knoxville near Lake Red Rock

Charming 2-bedroom NEW house with WiFi, AC Pella/Knoxville near Lake Red Rock

Knoxville
When you stay at this vacation home in Knoxville, you'll be 6 minutes by foot from Lake Red Rock.
Charming 2-bedroom NEW house with WiFi, AC Pella/Knoxville near Lake Red Rock
Pleasant Stay in Pella

Pleasant Stay in Pella

Pella
With a stay at this vacation home in Pella, you'll be within a 5-minute walk of Central Park and Scholte House Museum & Gardens.
Pleasant Stay in Pella
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Three bedroom townhome, blocks from idyllic downtown

Three bedroom townhome, blocks from idyllic downtown

Oskaloosa
With a stay at this vacation home in Oskaloosa, you'll be within a 15-minute walk of City Square Park and Oskaloosa Public Library.
Three bedroom townhome, blocks from idyllic downtown
Charming Iowa Abode Near Knoxville Raceway!

Charming Iowa Abode Near Knoxville Raceway!

Knoxville
Located in Knoxville, this vacation home is within a 15-minute walk of National Sprint Car Hall of Fame and Knoxville Raceway.
Charming Iowa Abode Near Knoxville Raceway!
Red Fern Hotel - Eclectic Getaway 2 bedroom

Red Fern Hotel - Eclectic Getaway 2 bedroom

Ottumwa
With a stay at this vacation home in Ottumwa, you'll be within a 15-minute walk of Pickwick Park and Greater Ottumwa Park.
Red Fern Hotel - Eclectic Getaway 2 bedroom
Spacious and charming 4br home in downtown Pella

Spacious and charming 4br home in downtown Pella

Pella
With a stay at this vacation home, you'll be centrally located in Pella, just a 4-minute walk from Historical Village, Vermeer Windmill & Scholte House and 7 ...
Spacious and charming 4br home in downtown Pella
Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More

Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More

Oskaloosa
With a stay at this vacation home in Oskaloosa, you'll be within a 5-minute drive of Mahaska Health and City Square Park.
Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More
Adorable Little Yellow House, Prime Location! Downtown Pella, IA

Adorable Little Yellow House, Prime Location! Downtown Pella, IA

Pella
With a stay at this vacation home in Pella, you'll be within a 5-minute walk of Central Park and Molengracht Plaza.
Adorable Little Yellow House, Prime Location! Downtown Pella, IA
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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.

Oskaloosa Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oskaloosa vacation homes are the perfect way for you to wing it.

Holiday houses in Oskaloosa let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oskaloosa in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oskaloosa adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oskaloosa with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oskaloosa vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oskaloosa Holiday Homes essential information

Accommodation
23 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Charming, modern and cozy retreat on the bike path, Charming 2-bedroom NEW house with WiFi, AC Pella/Knoxville near Lake Red Rock, Pleasant Stay in Pella, Three bedroom townhome, blocks from idyllic downtown, Charming Iowa Abode Near Knoxville Raceway!, Red Fern Hotel - Eclectic Getaway 2 bedroom, Spacious and charming 4br home in downtown Pella, Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More, Adorable Little Yellow House, Prime Location! Downtown Pella, IA

Top trending hotels in Oskaloosa

EverSpring Inn & Suites

EverSpring Inn & Suites

2.5 out of 5
2401 A Ave West, Oskaloosa, IA
Fully refundableReserve now, pay when you stay
With a stay at EverSpring Inn & Suites in Oskaloosa, you'll be 16.2 mi (26.1 km) from Central College and 20.4 mi (32.9 km) from Lake Red Rock.
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
Located in Oskaloosa, Fairfield Inn & Suites by Marriott Oskaloosa is within a 5-minute drive of Southern Iowa Fair and William Penn University.
Fairfield Inn & Suites by Marriott Oskaloosa
Cabin by Keomah State Park: Swimming Pool, Hot Tub Patio, Game Room, Trails

Cabin by Keomah State Park: Swimming Pool, Hot Tub Patio, Game Room, Trails

Oskaloosa
Located in Oskaloosa, this cabin is on a lake, within a 15-minute drive of Lake Keomah State Park and Mahaska Health.
Cabin by Keomah State Park: Swimming Pool, Hot Tub Patio, Game Room, Trails
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Budget Inn Oskaloosa

Budget Inn Oskaloosa

2 out of 5
1210 A Avenue East, Oskaloosa, IA
Located in Oskaloosa, Budget Inn Oskaloosa is within a 5-minute drive of Mahaska Health and City Square Park.
Budget Inn Oskaloosa
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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.

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^Subject to availability and chosen travel dates.