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Oskaloosa Holiday Rentals

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Holiday Rentals in Oskaloosa

The Nest - next to bakery and downtown

Oskaloosa
10.0 out of 10, Exceptional, (36)
"Very cozy and comfy "
United States
Curtis M.
The Nest - next to bakery and downtown

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

Oskaloosa
10.0 out of 10, Exceptional, (47)
"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! "
United States
Jaclyn W.
Cabin by Keomah State Park: Swimming Pool, Hot Tub Patio, Game Room, Trails

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

Oskaloosa
10.0 out of 10, Exceptional, (7)
"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...
United States
Jill
A Class-y & spacious 1500 square foot retreat in a century old brick schoolhouse

Luxury Lakefront Escape at Lake Keomah near Oskaloosa Iowa.

Oskaloosa
10.0 out of 10, Exceptional, (8)
"Pet friendly, family friendly."
United States
Akisha
The price is NZ$625
includes taxes & fees
16 Nov - 17 Nov
Luxury Lakefront Escape at Lake Keomah near Oskaloosa Iowa.

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

Oskaloosa
10.0 out of 10, Exceptional, (12)
"Great place "
United States
Brent B.
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.

Oskaloosa
10.0 out of 10, Exceptional, (63)
"Excellent as always! One of our favorite places to stay!"
United States
Emily K.
Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.

Lee’s Garden House

Oskaloosa
10.0 out of 10, Exceptional, (2)
"Lee's Garden House fit our family perfectly. It had just the right amount of space. It was cozy and felt like home. It was close to WPU which was perfect as we stayed there to take our daughter to college. I sent a couple of messages to Missy, and she quickly responded. We will stay there again or at one of their other properties. It was a great experience!"
United States
Renae C.
Lee’s Garden House

Brand New Stylish Condo near Trails & Downtown

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

Three bedroom townhome, blocks from idyllic downtown

Oskaloosa
10.0 out of 10, Exceptional, (4)
"Very responsive host. The living room area was dark. I let the host know and they delivered a lamp the next day. When the smoke alarm battery started beeping, the host came right over to change the battery."
United States
Paul C.
Three bedroom townhome, blocks from idyllic downtown

Historic Pella Cottage w/Firepit Retreat

Pella
10.0 out of 10, Exceptional, (63)
"The house was perfect for our family get away. We appreciated the comfort of the home and the location to many things. Would highly recommend staying at this house!"
United States
Sarah Y.
The price is NZ$361
includes taxes & fees
18 Nov - 19 Nov
Historic Pella Cottage w/Firepit Retreat

Studio Klokkenspel in Pella

Pella
10.0 out of 10, Exceptional, (48)
"The place was excellent above expectations, owner was responsive when questions were asked. We will stay there again."
United States
Rod
The price is NZ$419
includes taxes & fees
17 Nov - 18 Nov
Studio Klokkenspel in Pella

Spacious Pella Historic Home w/ideal location

Pella
10.0 out of 10, Exceptional, (46)
"This place was the perfect location for us. Easy walk to town. The beds were great and it was clean. Had everything we needed."
United States
Leslie J.
The price is NZ$714
includes taxes & fees
18 Nov - 19 Nov
Spacious Pella Historic Home w/ideal location

Cozy 2-bedroom mobile home in Knoxville

Knoxville
7.2 out of 10, Good, (5)
"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."
United States
Lisa S.
The price is NZ$218
includes taxes & fees
18 Nov - 19 Nov
Cozy 2-bedroom mobile home in Knoxville

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

Knoxville
10.0 out of 10, Exceptional, (37)
"Beautiful, relaxing cabin! Everything was just perfect! "
United States
Scott K.
Luxury Cabins with two person jacuzzi tub. Fabulous location near Lake Red Rock.

Lake Red Rock Cottage Retreat

Pella
10.0 out of 10, Exceptional, (41)
"House was clean and very spacious and a 5 minute drive to the marina. I would highly recommend it!"
United States
Heather S.
Lake Red Rock Cottage Retreat

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

Pella
10.0 out of 10, Exceptional, (3)
"Really loved our stay!! Home was immaculately clean and decorated tasteful. All house features were easy to use. Easy walk to downtown Pella."
United States
Erica S.
The price is NZ$466
includes taxes & fees
27 Nov - 28 Nov
Charming 2-bedroom cottage with WiFi, AC in lovely Pella

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

Knoxville
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!!!"
United States
Kevin V.
Knoxville Den: Walk to Track, Great for Families & Crews

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

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

Charming Iowa Abode Near Knoxville Raceway!

3.0 star property
Knoxville
8.0 out of 10, Very good, (1)
"There are no pet friendly hotels in Knoxville so we were very happy to find this pretty house for our stay when back for a family funeral. Pros: ample parking, good location, very clean, large space, nice kitchen, large yard, DISH TV, pet friendly, rapid response from owner, sleeps multiple people Cons: sleeps multiple people but only 1 key provided, couches don’t face TV, 2 BRs have no doors so there is privacy only for people in upstairs BR, outlet in basement bath not working "
United States
Barbara
Charming Iowa Abode Near Knoxville Raceway!

Riverfront Cabin Near Dtwn Pella w/ Game Room!

3.0 star property
Pella
Riverfront Cabin Near Dtwn Pella w/ Game Room!
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

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$218 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. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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.