Vacation rentals in Olney

The Shoe Inn, a modern apt in downtown Teutopolis

Welcome to The Shoe Inn! You'll be at the center of town within walking distance to all the places you need to be: banquet halls, five bars, restaurants, Wessel's grocery store, ice cream shop, church, hardware store, and community parks. Smart lock, contactless entry is available for a convenient & safe stay. Enjoy the full size washer & dryer (no detergent provided) , fireplace, kitchenette (no stove), free parking, Samsung 50" smart TV w/ 100's of cable channels, Alexa device, & free WiFi

The Adams Street Suite

This quiet, cozy home is tucked into a peaceful neighborhood—perfect for relaxing after a long day of travel, work, or adventure. The Adam’s Street Suite offers a comfortable feel with thoughtful touches throughout, including a coffee bar to jumpstart your mornings. Whether you’re visiting for a night or a longer stay, you’ll find everything you need to feel at ease. Clean, stylish, and designed for comfort—this is the perfect spot to rest, recharge, and enjoy your stay.

Wooden Shoe Factory, Historic, w/ Bar & Breakfast

Historic 1880 Wooden Shoe Factory by Wooden Shoe Maker Gerhard Deymann. A great getaway Tiny House from the past with a Bar & Books. Please take some & leave some :-) Fully furnished. Tons of charm. It has a loft, luggage lift, exposed brick/beams, fireplace, bikes, antiques, front sitting area, swing, grill, back patio, yard, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.

Lake Cabin in the Woods

🌲Looking for a relaxing getaway? Need a peaceful stopover on your Midwestern travels? Craving tranquility in a remote setting? Look no further—Lake Cabin in the Woods is your perfect retreat! Nestled about 60 miles from both Effingham, IL and Evansville, IN, our cabin offers the solitude you’re seeking without being too far from major highways. Located between Interstate 70 and Interstate 64, it’s a serene escape with easy access to wherever your journey leads.

Davis House

Very nice, recently remodeled Home in Fairfield. One bedroom with one and a half bath. The master bed is a king and amazingly comfortable. The Master bath is straight out of a magazine, tile shower, double vanity, and plush towels. The living room couch is a queen pull out. It's as comfortable as a hide a bed couch can be. Completely stocked down to coffee on us! Great location- midway down Main Street. Perfect central location.

Day of Rest

This place is in a private, residential neighborhood but only a few blocks from businesses, shopping and restaurants. There are two small parks for children to play at, nearby. There is plenty of parking for multiple vehicles or a commercial truck/trailer. Bright outdoor LED lighting provides a safe atmosphere. This property is attached to a small venue. The venue has a full kitchen area that can be rented for an additional fee.

Quiet Lake House By the Beach

Welcome! Quiet Lake House by the Beach is just as it describes! The property shares a driveway with the cabin I also host. The Lake House is located just a short walk to Beach, Pinky’s , The Rusty Reel Bar (below Pinky’s) and The Marina. The beach offers a beautiful playground, pavilions and a frisbee golf course!

Rustic Guest House Cabin in a Secluded Setting

Let this guesthouse be your home away from home! Guests will enjoy the rustic feel of the private guesthouse located on 1 acre of land and surrounded by mature trees. Nearby in Robinson there are historic sites, hiking & lakes, golf, wineries and much more!

Cozy Two Bedroom Home

Enjoy easy access to everything from this perfectly located home base. The newly renovated house is a one minute drive to Good Samaritan Hospital, three minutes from Vincennes University and across the street from the George Rogers Clark Monument and Park.