Vacation rentals in Oskaloosa

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Top-rated vacation rentals in Oskaloosa

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious bedroom is highlighted by a large bed dressed in neutral linens, accompanied by decorative pillows. Natural light enters through a window, illuminating the room's neutral walls and exposed brick accents. A mirror and lamp enhance the modern design, while a small plant adds a touch of greenery.
Loft in Williamsburg
4.97 out of 5 average rating, 130 reviews

1890 Lofts - Mayberry

Conveniently located right off I-80 near the historic Town Square in Williamsburg. A variety of restaurants, a coffee shop, grocery store, park for kids, and library are all within a 5 min walk. 3 min from 🛍Wburg Outlet Mall 5 min from ⛳️ Stone Creek Golf 10 min from🍷Fireside Winery 15 min from🥨Amana Colonies and🍺Millstream Brewery 25 min from ⚫️🟡 Kinnick, Carver, and U of I Hospitals-Go Hawks Looking for more room? Check out our other AirBnB at this same location 1890 Lofts - Harvester

Guest favorite
A light-filled living space features a cozy beige sectional sofa adorned with patterned throw pillows. A round, plaid ottoman sits in front, accompanied by a small side table housing books and decorative items. Natural light streams in through the large windows, enhancing the inviting atmosphere.
Home in Oskaloosa
4.94 out of 5 average rating, 139 reviews

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!

Guest favorite
An inviting interior showcases a spacious living area with wooden beams and a cozy couch. A colorful area rug lies on the polished floor, while the kitchen features dark cabinets and modern appliances. Light floods the space through large windows, enhancing the cabin's rustic charm.
Cabin in Malcom
4.97 out of 5 average rating, 198 reviews

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!

Top guest favorite
A cozy living area features a plush sofa alongside two armchairs positioned around a low table. Soft lighting from a nearby lamp creates a relaxed ambiance. Decorative elements, including a bookshelf and a neatly arranged rug, enhance the inviting atmosphere.
Cabin in Pella
4.96 out of 5 average rating, 171 reviews

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.

Top guest favorite
The exterior of a remodeled house is adorned with warm white lights, highlighting the entrance. A porch with two chairs is visible, alongside decorative plants and stones. The landscape features a welcoming pathway leading to the front door, surrounded by winter foliage.
Cottage in Pella
4.99 out of 5 average rating, 382 reviews

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.

Top guest favorite
A spacious studio apartment with an open floor plan is highlighted. Two reclining sofas are arranged around a coffee table, while a dining area features a table with white chairs. Natural light enhances the overall space, which is finished with modern flooring.
Apartment in Oskaloosa
4.95 out of 5 average rating, 192 reviews

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.

Top guest favorite
A modern kitchen is depicted with open wooden shelves displaying a variety of white and light blue dishware. A stainless steel range hood is mounted above a sleek gas stove, while a light countertop contrasts with the green walls and mosaic backsplash.
Home in Pella
5 out of 5 average rating, 128 reviews

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.

Top guest favorite
A well-appointed living room features a spacious sectional sofa, paired with a wooden coffee table. Natural light streams through large windows, accentuated by light curtains. A modern armchair and floor lamp provide additional seating and illumination. A television is mounted on a wooden console, with decorative elements enhancing the space.
Home in Pella
5 out of 5 average rating, 158 reviews

Modern Downtown Retreat In The Heart Of Pella

Enjoy the convenience of being a block from Pella’s square and all that the downtown area has to offer. This fully remodeled, 3 bedroom, 2 bath home offers you a centrally located base to plan your daily excursions. Whether your day is spent perusing the unique shops around the square, on the trails or water at Lake Red Rock, or meeting up with friends and family, this home will be the perfect place to recharge and refresh between activities.

Top guest favorite
A cozy living area features large windows providing natural light and a view of the town square. A brick fireplace is complemented by decorative elements, while a sectional sofa and a modern armchair create a welcoming seating arrangement. A small dining table is visible in the background.
Loft in Oskaloosa
4.96 out of 5 average rating, 112 reviews

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.

Top guest favorite
A cozy living area features a turquoise sofa topped with a patterned throw. A coffee table sits in front, with a small television on a vintage stand. Bright red curtains frame the window, while a decorative globe and record wall accents add a touch of charm.
Apartment in Pella
4.98 out of 5 average rating, 356 reviews

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.

Guest favorite
A cozy living area is showcased, featuring a comfortable sectional couch with decorative pillows. Windows allow natural light to illuminate the space, while a modern kitchen with white cabinetry and stainless-steel appliances is visible. A flat-screen TV is positioned on a wooden stand.
Home in Pella
4.98 out of 5 average rating, 124 reviews

Charming Pella retreat w/firepit by Central coll

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.

Top guest favorite
A log cabin with a green metal roof features a covered porch with two wooden rocking chairs. A pathway leads to the door, and a fire pit is situated in the yard. Surrounding trees create a natural barrier, enhancing the secluded setting.
Cabin in Newton
4.98 out of 5 average rating, 291 reviews

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

Frequently Asked Questions

  • What are the most popular amenities for Hotel Rentals in Oskaloosa?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in hotel rentals in Oskaloosa?

    Experience the best of Oskaloosa with our hotel rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Oskaloosa?

    Yes! Work meets play with ease at over 10 vacation rentals in Oskaloosa featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Oskaloosa have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Oskaloosa. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Oskaloosa have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Oskaloosa. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Oskaloosa?

    Oskaloosa has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about vacation rentals in Oskaloosa

  • Total vacation rentals

    Explore 20 vacation rentals in Oskaloosa

  • Nightly prices starting at

    Oskaloosa vacation rentals start at G$6,277 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,010 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oskaloosa vacation rentals include wi-fi 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!

  1. Airbnb
  2. United States
  3. Iowa
  4. Mahaska County
  5. Oskaloosa