Holiday rentals in Jefferson County

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.

Bright and Modern Home

Pets welcome in this sunny and cozy home! Just steps from the local dog park, and a short walk downtown. - 42” TV with most streaming services - Fully equipped kitchen including chef knives, Vitamix, and condiments - Free coffee with grinder & french press - NO CHORES! Just lock up and have a safe trip! Privacy: Guests have the entire main house. Host occupies basement unit with separate entrance. No shared spaces, and host never enters main house. Backyard is not available for guest use.

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.

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.

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!

Vastu Apartment in Maharishi Vedic City by Trails

Take it easy at this unique and tranquil getaway. 2 Bedroom, 2 Bathroom, desk and office chair, full Kitchen, bamboo floors. Each bed is Queen. All New: Queen mattress, AC system, W/D, and glass top stove! Comfy furnishings, plus enjoy our special wilderness 3.5 mile loop trail system right out your front door. Also great views out the bedroom windows. NOTE: no TV, ethernet or wifi is it available. Good cell service to use your own hotspot for getting online,

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 3 other apartments available at this location, if more space is needed for additional family or friends.

Leah’s Landing

Take it easy at this unique and tranquil cottage home. A small cozy space with a modern vibe. Newly remodeled, open concept space located on a quiet street where you can experience the peaceful advantages of a small town with the added convenience of being within walking distance to some parks, the hospital or downtown areas.