Photo by Hideki Yamagata

Oskaloosa Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Oskaloosa

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

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

10.0 out of 10, Exceptional, (37)
"Our stay was a very relaxing experience. The owners were very quick to respond to any of our questions and concerns. We did misread the listing and thought the house faced the lake in some way, but it's actually across the street (a very small street mind you) so it was a very quick walk to the actual lake. This is a lived in home so there are personal items like family photos around the place. The place was very clean and tidy, however it is an older home so it has its quirks. It felt like we...
Cabin by Lake Keomah State Park: Swimming Pool, Hot Tub Patio, Game Room, Trails
Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (8)
"The accommodations were wonderful!! Oversized living room with book and board games and the patio and pool area was a hit for everyone plus the game room was a great area and lower family room. There was something to do for everyone!!! Definitely recommend it!!"
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.
Miscellaneous

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

10.0 out of 10, Exceptional, (59)
"We had a great time there. We were very comfortable and cozy. We felt at home!"
Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.
The Nest - next to bakery and downtown
Beach

The Nest - next to bakery and downtown

10.0 out of 10, Exceptional, (26)
"Visiting our kids for Thanksgiving. Great location and very clean. Host was easy to communicate with! "
The Nest - next to bakery and downtown
Modern Oskaloosa Cabin w/ 2 Acres & On-Site Trails
Exterior

Modern Oskaloosa Cabin w/ 2 Acres & On-Site Trails

10.0 out of 10, Exceptional, (4)
"Ethan such a good guy help and respond to my all calls and text. Yard and surroundings were gorgeous and house perfect clean set up excellent."
Modern Oskaloosa Cabin w/ 2 Acres & On-Site Trails
Lee’s Garden House
Fridge, microwave, oven, stovetop

Lee’s Garden House

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!"
Lee’s Garden House
Brand New Stylish Condo near Trails & Downtown
Miscellaneous

Brand New Stylish Condo near Trails & Downtown

10.0 out of 10, Exceptional, (2)
"Shower was great! This place has a smart TV! I would definitely stay again!"
Brand New Stylish Condo near Trails & Downtown
Three bedroom townhome, blocks from idyllic downtown
Interior

Three bedroom townhome, blocks from idyllic downtown

Three bedroom townhome, blocks from idyllic downtown
Modern Oskaloosa Cabin w/ 2 Acres & On-site Trails
Interior

Modern Oskaloosa Cabin w/ 2 Acres & On-site Trails

3.0 star property
Modern Oskaloosa Cabin w/ 2 Acres & On-site Trails
Historic 4 bedroom home- walk to downtown
Property grounds

Historic 4 bedroom home- walk to downtown

10.0 out of 10, Exceptional, (25)
"This place was the perfect location for us. Easy walk to town. The beds were great and it was clean. Had everything we needed."
The price is HK$1,159
HK$2,665 total
includes taxes & fees
6 Jan - 7 Jan 2025
Historic 4 bedroom home- walk to downtown
Knoxville Den
2 bedrooms, WiFi, bed sheets

Knoxville Den

8.0 out of 10, Very good, (1)
"The place was fun and the neighborhood was WONDERFUL! The water had been shut off and the kitchen window was broken when we got there, but they fixed it right away. If you're looking for somewhere to stay when you come to watch the race this is perfect."
Knoxville Den
Blue Fern Hotel - Nestled Away Loft Space
Pool

Blue Fern Hotel - Nestled Away Loft Space

10.0 out of 10, Exceptional, (5)
"The apartment was cozy and perfect for our weekend stay. We would definitely book again."
Blue Fern Hotel - Nestled Away Loft Space
Private Water Side Cabins
Property grounds

Private Water Side Cabins

9.6 out of 10, Exceptional, (16)
"Great location, waterfront, dock, fishing, wildlife, comfortable, most amenities, thoroughly enjoyed the weekend stay. Gracious and polite hosts. Thank you."
Private Water Side Cabins
Luxury Cabins with two person jacuzzi tub. Fabulous location near Lake Red Rock.
Exterior

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

10.0 out of 10, Exceptional, (31)
"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.
Pristine getaway for groups; 5 BR - sleeps 16+
Private kitchen

Pristine getaway for groups; 5 BR - sleeps 16+

The price is HK$1,736
HK$3,059 total
includes taxes & fees
6 Jan - 7 Jan 2025
Pristine getaway for groups; 5 BR - sleeps 16+
Condo in Pella- Steps to Shops, Bakeries, and Iconic Windmill!
Smart TV

Condo in Pella- Steps to Shops, Bakeries, and Iconic Windmill!

2.0 star property
The price is HK$692
HK$1,515 total
includes taxes & fees
26 Dec - 27 Dec
Condo in Pella- Steps to Shops, Bakeries, and Iconic Windmill!
Tranquil cabin with Fireplace in Knoxville - perfect for a cozy getaway
Exterior

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

10.0 out of 10, Exceptional, (2)
"Beautiful cabin in the woods. Very comfortable and relaxing. Great host. Julie was awesome, very appreciated welcome basket waiting for us. Thanks so much for the hospitality. Will definately recommend to friends and family"
Tranquil cabin with Fireplace in Knoxville - perfect for a cozy getaway
Unwind at our private 4BR home near downtown Pella, IA!
Pool

Unwind at our private 4BR home near downtown Pella, IA!

10.0 out of 10, Exceptional, (16)
"Beautiful home with great location and easy to coordinate "
The price is HK$2,110
HK$4,521 total
includes taxes & fees
29 Dec - 30 Dec
Unwind at our private 4BR home near downtown Pella, IA!
Ophelia’s Huis in Pella
Property grounds

Ophelia’s Huis in Pella

10.0 out of 10, Exceptional, (2)
"Ophelia’s Huis is a beautiful home. We had a wonderful time hosting Thanksgiving for our family here. We will definitely be back. Everything was perfect!"
Ophelia’s Huis in Pella
Private Waterfront Cabins
Terrace/patio

Private Waterfront Cabins

9.8 out of 10, Exceptional, (41)
"Every enjoyable"
Private Waterfront Cabins
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.
Don't see what you're looking for?
See all available properties in Oskaloosa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Oskaloosa you may be interested in

EverSpring Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets

EverSpring Inn & Suites

2.5 star property
8.2 out of 10, Very good, (540)
"Room was updated and clean with a good TV. Wal-Mart is in walking distance."
The price is HK$770
HK$862 total
includes taxes & fees
30 Dec - 31 Dec
EverSpring Inn & Suites
Fairfield Inn & Suites by Marriott Oskaloosa
Lobby

Fairfield Inn & Suites by Marriott Oskaloosa

2.5 star property
9.2 out of 10, Wonderful, (185)
"All good."
The price is HK$853
HK$955 total
includes taxes & fees
29 Dec - 30 Dec
Fairfield Inn & Suites by Marriott Oskaloosa
Quality Inn Oskaloosa
Free daily on-the-go breakfast

Quality Inn Oskaloosa

2.0 star property
7.6 out of 10, Good, (428)
"Clean "
The price is HK$575
HK$644 total
includes taxes & fees
29 Dec - 30 Dec
Quality Inn 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.

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?

Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More: This highly rated holiday home rental in Oskaloosa offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. Another good choice for your trip to Oskaloosa is Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown..

How many holiday rentals are there in Oskaloosa?

Expedia has 4 holiday rentals for your stay in Oskaloosa.

What’s there to see and do in Oskaloosa?

Lake Keomah State Park and City Square 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 Edmundson Golf Course.

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.