Holiday rentals in Oskaloosa

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!

Historic Dutch Cottage • Walk to Central • Firepit

The Rock House • Historic• Walk to Central College• Fire Pit Stay in a true piece of Pella history. The Rock House was built in 1856 by Dutch homesteaders and has been beautifully restored with modern comforts. This cozy 2-bedroom cottage sits next to Central College and is just minutes from downtown shops, bakeries, and the famous Vermeer Windmill. Perfect for couples, small families, Central College visitors or a cozy Pella getaway, the home blends historic charm with a peaceful retreat.

The Attic on Front

Welcome to your home away from home in the heart of historic Brooklyn, Iowa! Located on the second floor of a downtown building, this space includes a full kitchen, office nook, bathroom, and a large living area with sleeping quarters. Enjoy beautiful downtown views, just steps from the Michael J. Manatt Community Center and Brooklyn Opera House. Centrally located between Des Moines and Iowa City, with easy access to I-80, this is the perfect spot to experience Brooklyn's charm and history.

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 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.

"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.

Stellapolis Lofts - The Evans

Modern + Historic Evans Suite combines "old brick charm" with modern comfort in this spacious 1300sqft unit located on the Square in Williamsburg where you'll be overlooking the bustling downtown and park. Just two minutes off I-80 you'll be close to: - Williamsburg Outlets - 2 minutes - Fireside Winery - 10 minutes - Amana Colonies - 15 minutes - Iowa Hawkeyes (University of Iowa, UIHC, Kinnick Stadium & Carver Arena) - 25-30 minutes

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.

Beautiful Plain Bungalow

The Belle Plaine Bungalow is a private two-bedroom home located in Belle Plaine, Iowa. Directly across the street from Anderson Park, it is in a neighborhood just walking distance from the local grocery store, Main Street, and the new Mexican restaurant down the street. There is private parking for up to 3 cars. There is also street parking.

Crestview Hill Home. Lovely 5.5 acre wooded area.

Welcome to Crestview Hill! Relax with the whole family at this peaceful place to stay. This three bedroom two bath home is in the absolute perfect location. Close to many restaurants and stores, yet tucked away in a quiet, beautiful wooded area with some lovely trails and a creek, you’re definitely going to want to come back often!