
Holiday rentals in Oskaloosa
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Top-rated holiday rentals in Oskaloosa
Guests agree: these stays are highly rated for location, cleanliness and more.

Sunny Cottage: FirePit, by Prairie & Wooded Trails
This bright, cheerful two bedroom home with full service kitchen, vaulted open living area, smart Weber grill, fire pit and private backyard is tucked away in a quiet neighborhood with easy access to a 14 mile paved recreation trail, nearly 1700 acres of forests, wetlands, prairies and parks to explore, local winery with dine in nights, cheese farm, museums and active art community. Guests will have easy access to the home with keyless entry. You'll find yourself rested, refreshed and reignited!

Quaint & Comfy in Pella, Iowa
This 1695 square foot home is the perfect fit for family, friends, and out of town business workers to enjoy the amenities of home. Guests are sure to enjoy a memorable stay in this newly remodeled 3 bedroom, 2 bath home. The 1st floor bedroom with it's queen size bed opens up to the backyard deck. Both bedrooms on the 2nd floor have queen size beds. The kitchen is fully equipped with all the amenities for cooking at home. New washer and dryer in the basement along with a 2nd bathroom w/ shower.

Bison Ranch*Cabin*Huge Views
Come to the place where the buffalo roam! Relax in our beautiful handcrafted cabin with one full bedroom and two oversized lofts. Take a stroll on a 1.6 mile trail to view America’s National Mammal. 3 miles from I-80. Stay connected with our reliable wifi or unplug to enjoy the sounds of nature from the wrap around deck and firepit. Bring your own food to grill or purchase bison burgers from our onsite retail store. Close to dining and recreation! Stunning sunsets at Sunset Hills Bison Ranch!

The Prayer Cabin
The Prayer Cabin is located at Lake Red Rock outside of Pella, IA. The cabin Is an Earthen/Berm home located on a 1 acre lot in a quiet & clean neighborhood. The lot boasts a wooded valley with many birds and squirrels to watch. The Prayer Cabin was recently remodeled with a brand new kitchen and bathroom. Our first guests asked us if Chip and Joanna were the creators of the design. 💚 Navy Blue cabinets, Tons of white shiplap and open shelving. Peaceful. A place of respite and relaxation.

The Strawtown Cottage - in downtown Pella
Completely remodeled 1865 original Strawtown Store of Pella conveniently located in one of the best small towns in Iowa. Three blocks to downtown Pella, 1 1/2 blocks to West Market Park, 2 blocks to Central football, baseball and softball complex. Enjoy the cottage charm with two private bed and bath suites, a family room with dining, full kitchen, front and side porch, laundry and large back yard. Off-street parking in the back. Luxury sheets on queen beds await after your adventures.

Downtown Oskaloosa Square
Brand new in 2021! 650 sf studio apartment in downtown Oskaloosa. Located on 3rd floor of commercial building, across the street from the iconic bandstand and Oskaloosa square. Elevator access to private 3rd floor. 10 foot ceilings, washer & dryer in unit, (2) 50" smart tvs with high speed wifi and cable tv included. Nectar memory foam Queen mattress, double reclining sofa. Plenty of closet space and furnishings for long stays. Professional property management office on main floor.

Pristine getaway for groups; 5 BR - sleeps 16+
Wildflower on Independence was designed to provide you with a relaxing, spacious, peaceful house to gather with family and friends! With five bedrooms, a fully equipped kitchen, open dining room, seven TVs, capacious family room, and beautiful bathrooms, you will have ample room to relax and fellowship. Whether you are planning a family reunion, girls getaway, or bridal shower, Wildflower will not disappoint! Come and be our guest while you enjoy the history and flavor of Pella, Iowa.

Dixon Block Loft
Dixon Block loft is a historical building renovated into a beautiful 2 bedroom loft apartment. Old historic charm is embedded into the style. Overlooks charming town square. Walking distance to stores and restaurants. We live locally to assist with anything needed. We can't wait for you to enjoy the local small town charm. Many events happen in December, Lighted Christmas Parade. In the summer time, the town square has many concerts.

60's Inspired Studio
Our awesome 60's Inspired studio has a mid-century vintage vibe! A quick walk to explore the unique city of Pella. Including the city park, historical buildings, restaurants, bakeries, meat markets, stores, Central College, movie theater and much more to explore. This is a second story walk-up; you will have a flight of steps to enter and exit. Private entrance and parking in driveway.

Little Cabin in the Woods - Great for Staycation!
Our little cabin in the woods is a great place for couples to relax, reflect and connect. Nestled on 115 acres of land, there are many trails to explore throughout the woods. Enjoy watching wildlife, laughing around a fire, sitting on the front porch watching the sunset, reading, playing games, and stargazing.

Charming retreat w/firepit near central college
Step into history in this restored 2-bedroom cottage just minutes away from Central College and downtown Pella. We include everything you need for a comfortable and memorable stay. Board games, coffee bar, and local guidebooks included Book now and make our charming cottage your Pella home-base!

Downtown Pella Klokkenspel Studio
Location, Location, Location! Pella at it's finest! Right next door to the Klokkenspel, 2 doors down from Cellar Peanut Pub, half a block to the Vermeer windmill and Pella Historical Village and right on top of Dutchfix restaurant! So many things to do and see all within walking distance.
Popular amenities for Oskaloosa holiday rentals
Other great holiday rentals in Oskaloosa

Grinnell Heritage Tiny House - On Organic Farm

Modern Dutch Bungalow

QUIET Hideaway,2BR, 2Bath, KING bed,The Guesthouse

Fantastic Geodesic tent by lake red rock

Great location + Price Clean and comfortable

The Attic on Front

Warm, inviting home in the heart of Pella

Modern Comfort on E 6th, Pella
Quick stats about holiday rentals in Oskaloosa

Total holiday rentals
Explore 20 holiday rentals in Oskaloosa

Nightly prices starting at
Oskaloosa holiday rentals start at £23 per night before taxes and fees

Verified guest reviews
Over 1,010 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oskaloosa holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oskaloosa rentals

4.8 Average rating
Oskaloosa stays are highly rated by guests – averaging 4.8 out of 5!
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