Holiday rentals in Ollie

Carriage House - Historic Louden Hay Trolley + EV

Welcome to our Historic Carriage House - where you can enjoy a luxurious stay surrounded by famous Louden Hay Trollies that were invented here in Fairfield! Relax and unwind while surrounded by curated vintage decor on a plush leather sofa. Hang out and cook your favorite food in our designer kitchen with quartz countertops. Freshen up while standing on heated marble bathroom floors. Located 1 block off the town square with quick access to parking, restaurants and shops. EV Charger outside.

Beautiful Riverview Studio- steps away from Depot

Enjoy an exclusive view of the River, the FM Train Depot and Old Fort Madison from this 2nd floor true-studio apt. The space has modern décor and all of the comforts of home. Railfans will enjoy the trains and river fans will enjoy the unique east-west river movement. There will be train sounds! The space comfortably sleeps two adults in its queen size Murphy bed. For the extra guest there is a queen size blow-up mattress or snuggle up on the couch. Please reach out with any questions.

Farm stay close to Iowa City, IA

15 min.-Iowa City, 5 min- Riverside Casino, & 35 min-Eastern Iowa Airport, Cedar Rapids, IA. Comfy beds, living room sectional pulls out to queen hide a bed, 32 acres of rolling hills, horseback riding (sm. fee)*, winter fun, & fishing pond. First 2 guests pay base price, then 3rd thru 10th guests pay an extra 30.00 EACH. NO PARTIES on our farm. We live on property in a separate home. Dogs welcomed (must be kenneled when you leave property)NOTE: NO OVEN in kitchenette. *contact for details.

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.

Charming 2 Bedroom Ranch

Enjoy a visit to Fairfield with all the comforts of having your own home! This clean and cozy single-story house is nestled in a quiet neighborhood, just a 12 minute walk from the local bakery. It has 1 bedroom with a queen and 1 with two twins, 1 full bath, a living room and a well equipped kitchen. There is a large yard that can be enjoyed while dining on the back deck. The unfinished basement has a washer and dryer and an additional working toilet & sink. The driveway can fit 2 cars.

A Taste of Heaven

Enjoy this unique and tranquil getaway, where all you will hear is a cacophony of birdsong. Enjoy the 2 mile walking trail that meanders through the exquisite 60 acres of secluded woods and pristine prairie. Just a one minute walk away is a beautiful 1 acre pond with canoe. Overlooking a small, organic, sustainable hobby farm, it is located just 4 miles north of Fairfield Iowa, where Oprah visited and declared it to be "America's most unusual town". Your place to relax and recharge.

Location Location Location

When they say location is everything, they were talking about Sandstone Haus. Located just a few steps from all the action of Main Street. Wineries, Brewery, eateries, bakery, and boutique shopping are waiting for you in Amana Colonies. Book your stay in this spacious one bedroom (queen size bed) and oversized living room suite that includes a queen pull out couch for additional guests, large eat in kitchen for four people. If you need a workspace, this suite has one! Book today.

Comfy one bedroom apartment near City Square

This newly remodeled apartment is comfortable and cozy and just a short distance from the city square. We look forward to your visit and hope our lifelong knowledge of the community will enhance your visit. This unit is a completely separate apartment, ready for your stay. Shopping services are also available. There is also a studio apartment available at this location, if more space is needed for additional family or friends.

Secret Garden

This luxuriously appointed mid century home opens onto a private deck and parklike garden. It feels like being in the country even though it is just a few blocks to the town square and similarly close to the university. The local grocery store is two blocks down an elley that feel like a country road. A truly tranquil retreat. Free bicycles make it easy to get around and enjoy the 17 mile bike trail that circles the town.

Renovated barn with a bar

Our guest house started off as an Hog house and has been converted to a relaxing retreat with all amenities! Located on a small acreage conveniently located along interstate 80 and across the street from Kinze manufacturing. Relax while sitting in the sun feeding the Koi fish. Grill some of your favorite steaks while watching the game on the big screen TV.

Blue Fern Hotel - Nestled Away Loft Space

Take an adventure to this eclectic loft nestled in the heart of “The City of Bridges.” Here you’ll find a unique and bubbly styled space, stocked with coffee & tea, a refreshing work area, and good vibes. Nothing beats a nearby river walk and an easy Iowa get-a-way.

Spacious Guesthouse in Oskaloosa

This spacious rental resides in a quiet neighborhood, just a short walking distance from the local University and the historic downtown. You will enjoy a fully stocked kitchen, a relaxing living space, and all the conveniences of home.