Holiday rentals in Ollie

Prairie Sunsets

Unwind in this peaceful and utterly private oasis. Thirty two acres of pristine prairie and stunning sunsets. Built using Stapatyaved principles that promote alignment with natural law, this home feels nourishing and harmonious. New bamboo floors, granite countertops, soothing color palette. Lounge in a hammock, relax by the firepit, explore the 2 mile walking trail, look for our resident owl in one of the two classic barns. Or have an adventure or meal in eclectic Fairfield, just 5 miles away.

Sigourney Summit *No cleaning fees* 2 night min.

Welcome to the Sigourney Summit! As our name implies, this spacious loft-style apartment on the top floor above "Sigourney Mercantile" awaits after you CLIMB up TWO flights of stairs (no elevators, sorry, so pack accordingly)! Once you reach the "summit” of your climb up the stairs, take a step back in time with retro-style furnishings & modern comforts of home. Kids are welcome. However, please note this is a loft-style apartment so beware it is not completely child-proof due to its design

Historic Steckel Carriage House

Relax by yourself or with the whole family at this charming 1910 carriage house. :) Fresh flower bouquet! Listen to vintage records on the record player. The fully functional kitchen, stocked with water bottles, yogurt, and my homemade granola, will keep you happy. :) Sleep in comfort on the king-size, full, and twin bed. The monitors, office chairs, Wi-Fi, desk and printer makes a remote workplace. Kids? We got you! A kid's indoor play area + outdoor playground. No Pets. There are stairs.

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.

Farmstead Suite

Leave the everyday behind. Turn onto a picturesque gravel road and discover your sanctuary: the Farmstead Suite in Memphis, MO's farming heartland. This isn't just a stay; it's an intimate experience for ultimate peace, luxurious privacy, and a connection with nature. Enjoy unparalleled solitude, yet you're just 5-10 minutes from a charming town and 40 minutes from vibrant Kirksville, MO. It's the perfect fusion of a remote, romantic hideaway and effortless access to everything you desire.

Vastu Chalet by the Lake

Deeply relax in this Vastu Chalet by the Lake. Enjoy the unique energy of this World Peace community near the Peace Palace and The Raj. Walk on trails around two man-made lakes. A 5-miles drive to Fairfield, MIU, and all downtown attractions. Enjoy the entire private top floor of this duplex. A 14-step, outdoor staircase leads to your apartment. Main room offers kitchen, dining area, two beds, a couch. Full bathroom with shower and tub + washer & drier. Master bedroom with Queen-size bed.

Shome/Horse Stables Located Near Lake Darling

Welcome to a truly unique stay, a labor of love originally designed as a dream home for my father. This property includes beautiful horse stables and open land for anyone seeking serenity. Every detail has been thoughtfully crafted, from cozy interiors to quiet outdoor spots perfect for reflection or connection. Whether you’re here to unwind, be with family or simply take in the tranquility, you’ll feel the care and intention that went into creating this special place.

Broken Spoke Ranch private tiki bar/lake

Relax at this adults only log cabin that sleeps 4 comfortably! Private tiki bar w/grill overlooking our lake which is stocked with bass, blue gil and catfish! It's Perfect for fishing and kayaking! We have a fire pit, bbq, walking path on property, outdoor seating, donkeys & mini horses on property. The house is stocked with what you need to cook/bbq! Near speedway, holiday lake, Williamsburg!

The Retreat at Fireside Winery

Welcome to your home away from home, thoughtfully designed for comfort and convenience. Located just steps from Fireside Winery and a short drive to Williamsburg, the historic Amana Colonies, and Iowa City, our retreat offers the ideal setting for both relaxation and exploration. Spend your days discovering local charm and your evenings unwinding in comfort.

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!

Indian Hollow Cabin

A peaceful getaway in a private log cabin with a view of the Chequest Creek. This cozy cabin has 2 bedrooms (1 queen, 1 full, 1 twin bed, and a pullout futon). Perfect for a group of hunters, a romantic getaway, or a family visiting the Villages of Van Buren. Included Tv, washer & dryer, full kitchen, and wifi.