Holiday houses in Oskaloosa

Lodge amongst the vines

This peaceful home away from home is waiting to entertain. The perfect , spacious getaway for the hunting party, family reunion, bachelorette weekend... This secure lock up and go lodge is nestled between picturesque vineyards, in the heart of the popular panoramic Cedar Valley Winery. Outdoor bliss. The perfect destination for the kids to safely play. Enjoy a glass of wine on our deck from our Tasting Room or on the private deck of the lodge as you barbecue to a perfect SE Iowan sunset.

Getaway on Grand King Bed

Stylish Stay Near the Fairgrounds & Downtown! Experience comfort and convenience in this fully remodeled 3-bed, 2-bath home. Perfectly located near the Iowa State Fairgrounds, downtown, and major interstates, it’s your ideal base for exploring the city. Enjoy a modern kitchen, cozy living spaces, free Wi-Fi, and a spacious backyard. Whether you're here for the fair, work, or play, this home has everything you need for a relaxing stay. Book now and make it your home away from home!

• Casa Dean sleeps 20 close to Fairgrounds •

Discover your dream getaway in this stunning 5-bedroom, 3-bath home, packed with space and style! With over 3,000 sq ft, soaring 11’ ceilings, and an open kitchen, it’s perfect for families or groups. Unwind on the huge covered patio or enjoy the sprawling 1-acre yard—ideal for kids and gatherings. Sleeps up to 20 with 13 cozy beds! Conveniently close to downtown, the fairgrounds, and the interstate, this gem combines comfort and location. Book now for a truly unforgettable stay!

Fran's Cottage

🏡 Your Ultimate Getaway Awaits! 🏡 Step into a world of comfort and charm at this delightful house, where every corner exudes relaxation. With a generous 950 sq. ft. of space, you'll find room to breathe and unwind. 🌟 Discover 2 cozy bedrooms offering the perfect retreat after your adventures. Nestle into a snug queen bed or opt for the versatile futon full bed with a twin bunk bed setup – comfortably accommodating up to 5 guests.

Antler Acres, 2 bedroom 1 bath, sleeps 6

We are now renting our beloved summer get away!! A perfect location and set up for your family!! Located in Antler Acres just 3 miles from the Honey Creek State Park boat ramp. The home has open concept living with an open living and kitchen area, that is bright and inviting with lots of windows. One bedroom has a full bed and the other has two sets of twin bunks. The bathroom has been completely updated.

Sunny Days Valley View Villa 3

Vacation paradise on Rathbun lake! 4BR, 3BA with large game room with extra sleeper sofa for the 4th bedroom, Large living room & Kitchen, all one level with laundry facilities. Huge yard to setup games or just enjoy running around. Has a large outdoor fire pit area to enjoy on a relaxing evening. Has a beautiful inground swimming pool off the back patio for those hot summer days and BBQ area.

Droptine Cottage

A back road get-away in Iowa's best deer country. Featuring all the comforts of home with 2 bedrooms (1 queen & 1 full/twin bunk bed). Relax outside on the deck or by the firepit. Perfect for a group of hunters, fishermen or a family visiting the Villages! Included TV, DVD, Washer & Dryer, Wi-Fi, Charcoal & Gas Grills. Daily or weekly rentals available.

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!

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.