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!

Charming Garden Suite at PineRidge Rose Farm

Experience the quiet beauty of the Iowa countryside at PineRidge Roses. Whether you’re here for the high-octane excitement of the Knoxville Raceway or the Dutch charm of Pella, our suite offers a fragrant, peaceful home base. As a guest, you’re staying on a developing a flower farm. While we are still growing and building our floral dreams, you might see active farm working during the day. The reward is a fresh, hand-picked bouquet waiting in your suite to brighten every morning of your stay.

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.

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. 💚 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.

Barn House on the Farm

Stay in a renovated hilltop barn, with views of the fields and forests below. Visit our grass-finished cattle and goats, take a cooking or writing class, or enjoy farm-fresh dinner and breakfast. Or simply sit around the fire with old friends, go fishing, or take a walk in nature. We are a fifth-generation farm focused on sustainability. Our two+ bedrooms can accommodate friends, couples or families. It's the farm of your childhood dreams and the kind we want to preserve for the future.

"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.

Monte Lofts, on the square. No Cleaning Fees!

Welcome to Monte Lofts in downtown Montezuma. This spacious, newly remodeled loft features a private, secured entrance, a huge, fully stocked kitchen with stainless steel appliances and a laundry room with front load washer and dryer. The bedroom features a large walk in closet and its own entrance to the laundry room and full bathroom. The living room, with floor to ceiling windows offers a great view of the historic downtown Montezuma square.

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.

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!