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Oskaloosa Holiday Rentals

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Holiday Rentals in Oskaloosa

A Class-y & spacious 1500 square foot retreat in a century old brick schoolhouse

10.0 out of 10, Exceptional, (5)
"This schoolhouse is SUCH a special place. The classrooms have been lovingly restored. The owners have included delightful touches throughout -- lockers in the bathroom, former teachers' names on the doors, chalkboards and chalk, pull-down maps (from 1949!), and so much more. We appreciated all the care that went into making us comfortable during our stay, from a basket of snacks to chilled water in the fridge to detailed instructions about how to operate the TV. We will be back again and again...
The price is NZ$578
includes taxes & fees
19 Oct - 20 Oct
A Class-y & spacious 1500 square foot retreat in a century old brick schoolhouse

The Nest - next to bakery and downtown

10.0 out of 10, Exceptional, (34)
"Great location. I wish there were two queen beds. Sometimes the traffic was a bit noisier than I would like. But overall a good stay."
The Nest - next to bakery and downtown

Luxury Lakefront Escape at Lake Keomah near Oskaloosa Iowa.

10.0 out of 10, Exceptional, (5)
"Well care for her, nicely decorated, the host has lots of amenities already stocked. They thought of anything that can improve the state of their guests."
The price is NZ$605
includes taxes & fees
30 Sept - 1 Oct
Luxury Lakefront Escape at Lake Keomah near Oskaloosa Iowa.

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

10.0 out of 10, Exceptional, (46)
"We all had the most amazing experience here! From the beautiful spacious home to the hot tub, patio fire pit, grill top stove, game rooms, etc. Will definitely be staying here again! "
Cabin by Keomah State Park: Swimming Pool, Hot Tub Patio, Game Room, Trails

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

10.0 out of 10, Exceptional, (12)
"Great place "
Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More

Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.

10.0 out of 10, Exceptional, (63)
"Great cottage! Great hosts. Perfect for us and our dogs. Thanks!"
Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.

Three bedroom townhome, blocks from idyllic downtown

10.0 out of 10, Exceptional, (4)
"Exactly as advertised, VERY clean and comfortable and the owners were amazing to work with. "
Three bedroom townhome, blocks from idyllic downtown

Brand New Stylish Condo near Trails & Downtown

9.4 out of 10, Exceptional, (3)
"Shower was great! This place has a smart TV! I would definitely stay again!"
Brand New Stylish Condo near Trails & Downtown

Lee’s Garden House

10.0 out of 10, Exceptional, (2)
"This place was very beautiful and cozy."
Lee’s Garden House

Lake Red Rock Cottage Retreat

10.0 out of 10, Exceptional, (40)
"We didn’t need to leave all weekend! So much to do and enjoy on the property."
Lake Red Rock Cottage Retreat

Charming 2-bedroom cottage with WiFi, AC in lovely Pella

10.0 out of 10, Exceptional, (1)
"It was a beautiful house and my now husband and groomsmen loved the comfy couches both upstairs and downstairs. "
The price is NZ$366
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom cottage with WiFi, AC in lovely Pella

Charming, modern and cozy retreat on the bike path

10.0 out of 10, Exceptional, (60)
"My family of four had a fantastic stay at this property! It is beautiful, clean, and is thoughtfully equipped. We relaxed and enjoyed the town of Pella. This was a perfect base for exploring the town. "
The price is NZ$366
includes taxes & fees
1 Oct - 2 Oct
Charming, modern and cozy retreat on the bike path

Home In Eddyville

10.0 out of 10, Exceptional, (15)
"This property was perfect for me. I was traveling alone and enjoyed the quietness of the area. Very great stay. "
Home In Eddyville

Luxury Cabins with two person jacuzzi tub. Fabulous location near Lake Red Rock.

10.0 out of 10, Exceptional, (37)
"Nice and quiet!! Had everything we needed and the screened in patio was perfect!!!"
Luxury Cabins with two person jacuzzi tub. Fabulous location near Lake Red Rock.

Private Water Side Cabins

9.6 out of 10, Exceptional, (20)
"So peaceful!We named the goat Chocolate and the dog Puppy"
Private Water Side Cabins

Knoxville Den: Walk to Track, Great for Families & Crews

9.0 out of 10, Wonderful, (2)
"Great place to stay. Everything we needed! Easy to work with and check in was so easy. Also walking distance for anything we needed!! Highly recommend!!!"
The price is NZ$666
includes taxes & fees
8 Oct - 9 Oct
Knoxville Den: Walk to Track, Great for Families & Crews

Tranquil cabin with Fireplace in Knoxville - perfect for a cozy getaway

10.0 out of 10, Exceptional, (8)
"Great cabin, the fishing was outstanding, hosts were exceptional! "
Tranquil cabin with Fireplace in Knoxville - perfect for a cozy getaway

Walk to Knoxville Raceway! 3BR, Fire Pit, Near Lake Red Rock & Pella

9.8 out of 10, Exceptional, (11)
"Very clean and nicely decorated. It has everything you need!"
The price is NZ$772
includes taxes & fees
13 Oct - 14 Oct
Walk to Knoxville Raceway! 3BR, Fire Pit, Near Lake Red Rock & Pella

Spacious and charming 4br home in downtown Pella

10.0 out of 10, Exceptional, (40)
"This house is beautiful, and the host, Andrea, is very responsive to any questions you might have. Easy check in and out. I was traveling with friends from The Netherlands. They wished they could buy the house, haha! "
The price is NZ$662
includes taxes & fees
30 Sept - 1 Oct
Spacious and charming 4br home in downtown Pella

Cozy 2-bedroom mobile home in Knoxville

7.0 out of 10, Good, (2)
"Kristi’s trailer was exactly as described—cozy, comfortable, and equipped with everything we needed. The central air was a lifesaver in the August heat, and the location couldn’t be better for a quick trip to the racetrack. We appreciated how close it was to all the conveniences of Knoxville. Kristi was friendly and very responsive to messages, which made our stay even easier."
The price is NZ$213
includes taxes & fees
30 Oct - 31 Oct
Cozy 2-bedroom mobile home in Knoxville
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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Top Oskaloosa Hotel Reviews

Find out more about Oskaloosa

Find out more about Oskaloosa

Everything you need to know about Oskaloosa holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oskaloosa holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oskaloosa holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oskaloosa holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oskaloosa. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oskaloosa holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oskaloosa holiday rentals we have selected for you start as low as NZ$213 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oskaloosa rentals

At Expedia, we put the best Oskaloosa holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oskaloosa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oskaloosa holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oskaloosa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oskaloosa?

Yes, there are holiday rentals in Oskaloosa close to Southern Iowa Fair, or you can select a more secluded option if you're looking for a relaxing stay. Oskaloosa is known for its churches and coffee shops. Make sure you have time to check out the university setting and football games during your trip.

What are some of the best holiday rentals that Oskaloosa has to offer?

Luxury Lakefront Escape at Lake Keomah near Oskaloosa Iowa.: This highly rated holiday home rental in Oskaloosa is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games. Some other top choices in Oskaloosa are Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More and Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown..

How many holiday rentals are there in Oskaloosa?

Expedia has 5 holiday rentals for your stay in Oskaloosa.

What’s there to see and do in Oskaloosa?

City Square Park and VanderWilt Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Southern Iowa Fair and Lake Keomah State Park.

What’s a holiday rental in Oskaloosa like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oskaloosa. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family gatherings.