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Oskaloosa Vacation Rentals

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Vacation Rentals in Oskaloosa

Interior
Lake Cabin: Hot Tub, Fire pit, Patio, Pool table, Ping Pong, Trails, Kayaks
10.0 out of 10, Exceptional, (29)
"The cabin by the lake is great for family fun! The kids loved playing on the water with the kayaks and the pedal boat. We got to enjoy fishing, hiking, and lots of bike rides."
Lake Cabin: Hot Tub, Fire pit, Patio, Pool table, Ping Pong, Trails, Kayaks
Beach
Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.
10.0 out of 10, Exceptional, (55)
"Love the house and location. This is our second time staying here. We had a small issue with the smoke alarm going off and it stressed out our dogs otherwise we had a great time!! Highly recommend this home!!!"
Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.
Fridge, microwave, oven, stovetop
Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More
10.0 out of 10, Exceptional, (4)
"This house was a perfect gathering for our large family of all ages, to celebrate our Mother’s Birthday. There is a large great room that was comfortable and spacious to have our Talent Show, and personal tributes speeches. The kitchen/dining area is large and well appointed. I was able to prep food and serve food for 25 people. The lower level had a complete game room for the teens and young ones. The outdoor patio offered plenty of space, a firepit and pool. It was the perfect 4 day weekend...
Entertain Large Groups Here: Game Room, Pool, Patio, Fire Pit, Pool Table & More
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Beach
The Nest - next to bakery and downtown
10.0 out of 10, Exceptional, (20)
"Both my daughter and I loved the place. Very comfortable. Loved the view from second floor. Only two issues 1. Water never seemed to get warm enough. 2. the traffic from the cross street often noisy at night.. Aside of these two issues, the stay was great! Might come back again."
The Nest - next to bakery and downtown
Exterior
Modern Oskaloosa Cabin w/ 2 Acres & On-Site Trails
10.0 out of 10, Exceptional, (1)
"Property is nice and secluded. Very quiet and calm."
Modern Oskaloosa Cabin w/ 2 Acres & On-Site Trails
Fridge, microwave, oven, stovetop
Lee’s Garden House
Lee’s Garden House
Iron/ironing board, free WiFi, bed sheets
Brand New Stylish Condo near Trails & Downtown
10.0 out of 10, Exceptional, (1)
"Very cute!! Comfortable beds!!"
Brand New Stylish Condo near Trails & Downtown
Smart TV, books
Three bedroom townhome, blocks from idyllic downtown
Three bedroom townhome, blocks from idyllic downtown
Interior
Modern Oskaloosa Cabin w/ 2 Acres & On-site Trails
3.0 star property
Modern Oskaloosa Cabin w/ 2 Acres & On-site Trails
Property grounds
Private Waterfront Cabins
9.8 out of 10, Exceptional, (37)
"Enjoyed our nice quiet getaway!"
Private Waterfront Cabins
Exterior
Historic Cottage- The Rock House
10.0 out of 10, Exceptional, (13)
"Idyllic. The Rock House reminded us of the adorable, cozy, and charming cottage from the movie Holiday. Thank you for sharing your special place to create some priceless memories!"
The price is CA $198
CA $358 total
includes taxes & fees
May 27 - May 28
Historic Cottage- The Rock House
Property grounds
Private Water Side Cabins
10.0 out of 10, Exceptional, (8)
"The cabin is located on a farm in a very peaceful setting. The resident dog greeted us daily and was a welcome sight. The cabin is comfortable and overlooks the water. It was a very peaceful stay! Would recommend it if you want to unplug!"
Private Water Side Cabins
Iron/ironing board, free WiFi, bed sheets
Custom luxury retreat in the Knoxville area
10.0 out of 10, Exceptional, (70)
"The experience was great, met every need. An Iowa storm rolled through and we were afforded security for us and our vehicle."
Custom luxury retreat in the Knoxville area
Fridge, microwave, oven, stovetop
Adorable "Little Yellow House," Downtown Pella
Adorable "Little Yellow House," Downtown Pella
Exterior
Unwind at our private 4BR home near downtown Pella, IA!
10.0 out of 10, Exceptional, (3)
"Excellent. Lots of room. Beautifully furnished. Well supplied kitchen. We appreciated the puzzles & cards. Great linens. Complementary wine. Just a few tiny things. The bathroom door upstairs does not securely latch. Nightlights & tissue in the bathrooms would be nice."
Unwind at our private 4BR home near downtown Pella, IA!
Exterior
Quaint Montezuma Cabin Near Lake Ponderosa!
10.0 out of 10, Exceptional, (4)
"This property is absolutely fantastic! The owner was super friendly & hospitable. The interior was clean & well maintained. They didn’t spare any expense (like some VRBO’s do) on the mattress. It was super comfortable & I slept like a log. Super quiet & somewhat remote leads to a very nice stay. Take a chance on this we’ll kept secret. You won’t be disappointed."
Quaint Montezuma Cabin Near Lake Ponderosa!
Living area
3rd & Main Studio Martini
10.0 out of 10, Exceptional, (3)
"Brian and Candi were amazing hosts. Warm, hospitality and extremely accommodating. They are the kind of folks you don’t easily forget."
The price is CA $273
CA $347 total
includes taxes & fees
May 29 - May 30
3rd & Main Studio Martini
Private kitchen
Red Fern Hotel - Eclectic Getaway 2 bedroom
9.8 out of 10, Exceptional, (9)
"perfect accommodations for a couple of nights while visiting relatives"
Red Fern Hotel - Eclectic Getaway 2 bedroom
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."
The price is CA $137
CA $384 total
includes taxes & fees
May 27 - May 28
Knoxville Den
Property grounds
Historic 4 bedroom home- walk to downtown
10.0 out of 10, Exceptional, (17)
"Great location for walking to the square; perfect for a gathering, lots of space for visiting and dining room great for card/game playing. Highly recommend!"
The price is CA $318
CA $615 total
includes taxes & fees
May 27 - May 28
Historic 4 bedroom home- walk to downtown
Don't see what you're looking for?
See all available 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.

Other types of properties in Oskaloosa you may be interested in

Desk, iron/ironing board, free WiFi, bed sheets
EverSpring Inn & Suites
2.5 star property
8.2 out of 10, Very good, (462)
"It’s just what you expect, an older hotel with no frills but it is very clean and comfortable to stay "
The price is CA $135
CA $152 total
includes taxes & fees
May 27 - May 28
EverSpring Inn & Suites
Lobby
Fairfield Inn & Suites by Marriott Oskaloosa
2.5 star property
9.2 out of 10, Wonderful, (155)
"The breakfast was a pleasant surprise. The variety of choices were great! It had something for everyone."
The price is CA $191
CA $214 total
includes taxes & fees
May 26 - May 27
Fairfield Inn & Suites by Marriott Oskaloosa
Exterior
Super 8 by Wyndham Oskaloosa IA
2.0 star property
7.4 out of 10, Good, (401)
"Room and bathroom clean. Appreciated the refrigerator with freezer to freeze our cooler refreezable ice pack. Could improve on the breakfast selection, and quantities. We came down at 8 AM and their was very little left."
The price is CA $86
CA $96 total
includes taxes & fees
Jun 2 - Jun 3
Super 8 by Wyndham Oskaloosa IA
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.

Everything you need to know about Oskaloosa vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oskaloosa vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oskaloosa vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oskaloosa vacation rentals we have selected for you start as low as CA $137 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 vacation 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 vacation.

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 vacation rentals in Oskaloosa?

Yes, we offer vacation rentals in Oskaloosa close to Southern Iowa Fair, or you can choose a more remote option if you want a relaxing stay. Oskaloosa is known for its churches and coffeehouses. Make sure you have time to check out the university setting and football games during your trip.

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

Sunny Cottage: Fire pit, close to biking & walking trails and historic downtown.: This highly rated vacation home rental in Oskaloosa offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Oskaloosa?

Expedia has 4 vacation 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 Edmundson Golf Course.

What’s a vacation rental in Oskaloosa like?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Oskaloosa. Vacation rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

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