Holiday houses 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.

Crescendo Chalet

Keep it simple at this peaceful and centrally-located home. Perfectly situated walking distance to the MIU Campus, Everybody's and walking trails, our cozy and beautifully appointed, East facing chalet will have you starting each day with a smile on your face. With off street parking, this single story home features a fully equipped kitchen and laundry with dedicated ironing board. Perfect for short or long stays. The home is renovated but old - uneven flooring and imperfect finishing work.

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.

Winery - Vineyard Rustic Cabin

The Cabin is located on the site of Wooden Wheel Vineyards and Winery. For over 80 years this building served as a summer kitchen and wood shed for the main house, which was removed in the 60's. It was turned into a weekend cabin in the 90's and remodeled for your enjoyment in 2018. On site you can enjoy free wine tasting and a tour of the vineyard and winery. If the urge strikes you, you can have some R&R by helping out in the vineyard. Or, just take a walk back to our timber.

Vastu Chalet by the Lake

Deeply relax in this Vastu Chalet by the Lake, set on a one-acre lot. Experience the unique energy of this World Peace community near the Peace Palace and The Raj. Walk for miles on trails around two man-made lakes. Drive just 5 miles to Fairfield, MIU, and all downtown attractions. Enjoy the entire private top floor of this duplex. A 14-step staircase leads to your apartment. We live conveniently downstairs—feel free to reach out anytime.

Bluff View - 2B

Rest and relax in this spacious downtown apartment! Do you love to cook? Each of our apartments are over 1000sq feet and have beautiful kitchen and a dining areas. Stay with us as a weekend or extended stay traveler looking for a quiet location to unwind in. Centrally located in downtown Ottumwa, the property is within walking distance to restaurants, coffee, frozen yogurt, bars, downtown shopping, the bike trail and Bridge View Center.

Comfy Downtown studio apartment

Close to the city square, studio apartment is quiet, with beautiful city views. Furnished with character and comfort. This unit is newly remodeled and ready for your stay, whether one night or a week. Television and wi-fi, with on-site laundry. There are 4 apartments in this location, so book more than one and bring more friends & family!

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.