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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.

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

Mid-Century Modern Farmhouse Sanctuary

Filled with Balinese art & handmade solid wood furniture, this home is owned by a filmmaker who spends their time between Bali, Austin, & Fairfield. Plenty of space for entertaining, a chef’s kitchen and even its own yoga studio (note: this is listed as the “gym” in photos — yoga mats/no gym equip). This stylish sanctuary is perfect for family, group trips or just a private getaway in this sweet little town. There are 2 extra futon beds that can comfortably be made up in yoga room upon request.

A Stone's Throw

Take a break and unwind at this peaceful country home just outside of city limits. A Stone's Throw from the interchange of highway 1 and highway 34, as well as the hospital and all that Fairfield offers. This charming cottage has a spacious living room complete with a murphy bed that folds into a desk during the day and has a barn door to close it off as an extra bedroom at night. Enjoy the stocked kitchen, grill on the deck or sit on the porch and soak in the charm of this country cottage.

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.

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.

Luxury Downtown Loft | Rooftop + Sauna | Sleeps 12

One of the only places in Fairfield designed specifically for groups—this downtown loft lets you stay together, relax on a private rooftop patio, and unwind in the sauna or jacuzzi tub, all just steps from the town square. Whether you're visiting for a wedding, event, work trip, or weekend getaway, this is the ideal place to stay and sleep up to 12 in comfort. Walk downstairs to the town square, bars, wine bar, boutique, and restaurants. Unwind on the rooftop patio and enjoy the sunset!

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.

Luxury 1st Floor Apt Near Square

Experience the best of Fairfield at this stunningly remodeled apartment in an 1858 farmhouse. You'll be just a few minutes walk to Fairfield Square with its unique art, cafe, and dining scene. The master bedroom features a sliding door to a covered porch overlooking a larger patio ready for a party. Walk the beautiful grounds with an organic garden and orchard. Help yourself to produce in season. I enjoy meeting and interacting with my guests as they wish.

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.

The Little Red House

A beautifully appointed two bedroom home, meticulously cared for in the heart of town. Near grocery (just down the alley), coffee, music, restaurants and a farmer's market. Free use of bikes on request.