Holiday rentals in Greenup

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 Candy Kitchen

Take a step back in time as you enter this authentic 1930's Soda Fountain located in downtown Greenup Village of the Porches situated on the Historic National Road. The Loomis Family immigrated from Greece and operated the Soda Fountain and Confectionary until the 1960's. It has since been transformed into a spacious and comfortable living area with the original Soda Fountain still intact, beautiful tin ceiling, and also includes a large kitchen, a separate shower room & powder room.

Park View Place 4 Blocks From the World's Biggest

Park View Place 2 bedroom 1 bathroom 1 level with a small yard, multiple parking spaces in the front of the home with wheel chair access ramp to the front door. 4 blocks of The World's Largest Things just across from the Fairview Park that has 2 fishing ponds with Trout in them, a playground, a horse arena, camping area and ball fields. The neighborhood is very nice. We also offer a new 6 seater Golf Cart available for Rent to our 3 houses on a first come first serve basis.

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.

Sweet Dreams Cabin. Peaceful & Relaxing

Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

Country cottage tiny home.

This 240sq ft cottage offers big living in a tiny space. The cottage is on our 2 acre property that is used for a hobby farm and primary residence. The cottage features luxury vinyl flooring, granite counter tops and an updated farm house feel. The queen size bed is sure to provide the right amount of comfort. When you wake up, walk on over and grab a cup of coffee from the keurig. Enjoy a walk around to see the goats and chickens before heading off for the day.

One bedroom apartment above garage

One bedroom apartment above a garage in a small and quiet town with fast fiber Internet. We are located in the middle of Shelbyville, Effingham, and Mattoon. 10 minutes to Hidden Springs State Forest. 20 minutes to Lake Shelbyville, Lake Sara, and Lake Mattoon. 20 % off per night for stays longer than 7 nights. 30% off per night for stays longer than 28 nights. Ideal for up to 2 traveling workers.

Bev's Country Cottage

A small quiet cottage off the beaten path, located only minutes from Newton Lake Fish and Wildlife Area. This is a great place for hunters, fishermen or just someone that wants to get away from the city. It has exactly what you need to enjoy a long weekend full of the great outdoors. As hosts we want our guest to enjoy their stay so we are available to help with anything.

Cabin by the Creek‼️🏡🎣🦌

This is a private, unique cabin that sits on 7 acres with plenty of room to roam. There is a small stocked pond that is great for fishing. Maintained walking trails around the property for easy exploring. Sit on the porch or around the firepit and watch the wildlife that frequent the area.