Vacation 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.

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.

Fillmore’s Retreat

Welcome to the Fillmore Retreat. Enjoy a beautiful kitchen fully stocked with essential cookware & all new appliances , plus a bathroom featuring a double vanity & tiled shower/tub combo. Sleeps up to 5 guests across 3 bedrooms: (1 king, 1 queen, and 1 twin). Relax in the comfortable living spaces or work remotely with the dedicated office desk. For added comfort & cleanliness, the home features an Aurabeat sanitizing air purifier, and all windows are equipped with blinds for privacy & comfort

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

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.

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.

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.

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.

Rustic Ridge Retreat

Enjoy a private hot outdoor shower under the stars at this beautiful 24-ft yurt on a peaceful Iowa homestead. Elevated deck with a grill, fire table, sectional and sweeping prairie views. Inside - a giant skylight dome over a plush queen bed, sofa bed, kitchenette, WiFi, and air conditioning. XL Games (Tetris tumble, etc). No running water, but we supply fresh Culligan jugs, a clean flushable porta-potty with sink and light, plus the new outdoor shower. Free YMCA day pass per day. Max 4.✨

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 pond/timber.

Be at Home in Washington, Iowa

Be at Home on South Avenue B in Washington, Iowa! This cozy yet spacious home is centrally located in Washington just blocks from shopping, dining & coffee on the square or just over 1 mile to the Washington Wellness Park and trailhead of the Kewash Trail. Our home offers two bedrooms and one full bath with laundry. Bedroom 1 has a king bed and sitting area while bedroom 2 can be configured with 1 king or two twin beds allowing flexibility for your stay.

Cozy Cottage

Enjoy a cozy stay in a private cottage nestled in on a beautiful tree-lined street. Wayland is a small, friendly community in Southeast Iowa. It’s just a short drive—10 miles north to Washington, 20 miles south to Mt. Pleasant (County Seat), or 40 miles to Burlington, Iowa City, or Ottumwa—offering small-town living with nearby city amenities. We are available to assist you with any needs, as we live right in Wayland. We look forward to your visit.