
Vacation rentals in Oskaloosa
Find and book unique accommodations on Airbnb
Top-rated vacation 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.

Niland Nook
Relax with the whole family at this peaceful 3 bedroom, 2 bath house nestled in the farming countryside. Whether your in the cozy living room, sitting out in the screened in porch, or spending time in the private backyard....this house has all the amenities to make your stay an enjoyable one. Cows and calves can be seen for that added country experience. Several local attractions and nearby activities are just 15 minutes away in Oskaloosa, Iowa. Just a short 27 miles from Interstate 80.

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. đź’š 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.

Heart of Downtown Pella
Welkom to Heart of Downtown Pella! This charming stay is within steps of Pella’s most popular features: Quaint shops, vibrant restaurants, and of course Jaarsma & Vader Ploeg Bakeries, Vermeer Windmill, the Pella Historical Village, and more! !CAUTION! The stairway is very steep and is the only way to access the condo. Please take this into consideration if you have limited mobility and/or other reasons that may prohibit you from utilizing the stairs. PLEASE BOOK AT YOUR OWN DISCRETION.

"The Lost Gem" A little bit country...
Get ready to enjoy good 'ole country livin' when you choose to stay at our little cottage, The Lost Gem. Its a quiet retreat, recently renovated on a hard surfaced road with all the privacy you could desire. The yard is large enough to sit outside, giving children area to run .While enjoying the spacious outdoors, you'll be able to gaze at the beautiful sunsets each day. The entrance is very accessible and well lit to welcome you. Our guests enjoy a single level home with no steps.

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.

The Rock House-A cozy cottage w/ firepit in Pella
Welcome to The Rock House — your cozy Dutch cottage getaway! Built in 1856, this historic 2-bedroom, 1-bath home blends original charm with modern comfort. Enjoy a fantastic location next to Central College, a short walk to the square, and quick access to Lake Red Rock. Peaceful, private, and fully updated, it’s the perfect place to relax while staying close to everything Pella offers.

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.
Popular amenities for Oskaloosa vacation rentals
Other great vacation rentals in Oskaloosa

Little House on the Driveway

Hilltop Haven -Nestled in Nature

Cozy Country Retreat

The Koru Guest House

Modern 1 Bedroom. Free Parking on Site.

"Ms. Becky's Bungalow"

Vintage Downtown Loft

Rathbun Oaks
Destinations to explore
- Chicago Vacation rentals
- Platteville Vacation rentals
- Downtown Chicago Vacation rentals
- St. Louis Vacation rentals
- Kansas City Vacation rentals
- Minneapolis Vacation rentals
- Wisconsin River Vacation rentals
- Lake of the Ozarks Vacation rentals
- Milwaukee Vacation rentals
- Omaha Vacation rentals
- Twin Cities Vacation rentals
- North Side Vacation rentals




