Vacation rentals in Shelby County

Atop The Shop II | Spacious Downtown Loft

Atop the Shop II is a beautifully restored 1,800 SF loft in the heart of Downtown Shelbyville. This spacious apartment blends modern amenities with the character of a century-old building, giving you the best of comfort and charm. With plenty of room for families or groups to spread out and relax, it’s perfect for lake weekends, weddings, or a simple getaway. Less than a block from restaurants & shops, and just a mile from Lake Shelbyville. Historic charm. Modern comfort. Unbeatable location.

3-Acre Country Escape | Wildlife | Total Serenity

A freshly updated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, Amish country, and more. If you are looking for peaceful nights, this place is for you! Surrounded by mature trees and nature, where many days you will catch deer roaming the yard. Plenty of yard space for games, a fire table to converse around, and chairs on the porch to sit back, relax, and take in the tranquil sounds that surround you here at Lakewood Cottage #1.

Asa Creek Cottage

This open concept cottage offers the perfect blend of nature and modern comfort for families and small group gatherings. Enjoy the creek side deck, and listen to the gentle sound of the little waterfall nearby. On cooler evenings, gather around the fire to warm up. The interior boasts a spacious design, close to The Little Theatre on the Square, walking trails, and Lake Shelbyville with boating, fishing and swimming. Relax with a modern kitchen, 3 bedrooms, 2 bathrooms and a rainfall shower.

A Novel Stay

Enjoy peace and nature in this 3 bd 2 bath log cabin located on 3.5 acres of wooded property just a few minutes from Lithia Marina at Lake Shelbyville, IL. This home features a fully stocked kitchen, Blackstone, 6 person hot tub and large solo fire pit. It comfortably sleeps 8 and can flex up to 11, if needed. There are 3 Roku Tv's, bluetooth speakers and many family friendly games for your use. Come stay at a Novel Stay "Into the forest I go, to lose my mind and find my soul".- John Muir

Ultimate Country Home!

The Hideaway at Lake Shelbyville LLC is a privately owned, secluded shed house. This house can accommodate multiple boats and trailers of any size. It is a perfect house for a weekend getaway or a weeks' vacation in the heart of Lake Shelbyville. This country home is only 2 miles from Lone Point, 2.8 miles for Coon Creek, and 6 miles for Eagle Creek Boat Launch. This amazing house also has a 4,800 sq ft shed with a pickle ball court, badminton, corn hole, basketball hoop, and much more.

Charming Victorian Getaway by Lake Shelbyville

Nestled just 1.6 miles from Lake Shelbyville, this restored Vintage Victorian is the perfect retreat for families and friends. With three cozy bedrooms, a full kitchen, and a relaxing patio overlooking an old brick road, it is made for unwinding and making memories. Shelbyville’s history, parks, shops, and scenic trails offer endless exploring. Located 116 miles from St. Louis and 209 miles from Chicago, this charming home blends comfort, character, and small-town beauty for every guest.

Evergreen Pond

Relax with the whole family at this peaceful place to stay. This house sits on 5 private acres w/ a stocked fishing pond. The back yard has 6’H fence & there is a dog door for Fido. The Wilburn Creek Rec area & boat ramp is only 1.6 miles. This property has room to park your boat & your RV. Enjoy sitting on the porch swing, playing pickleball on your private court or shooting some hoops. You also have access to a 2 car garage. The basement offers Pop-a-shot basketball & ping pong.

Prairieview Cottage Retreat - Hot Tub Sunsets

REST, RELAX, RETREAT... Escape to tranquility at this picturesque, pet-friendly cottage, nestled in the serene countryside. Whether you're coming for a romantic retreat, family getaway, or a solo sanctuary, this charming haven offers a wonderful blend of comfort and serenity. Enjoy stunning sunsets from the hot tub, cozy up by the firepit on the patio, or simply unwind indoors in comfort. This retreat is ideally located in the heart of Illinois Amish country and near Lake Shelbyville.

The Bin at No Bad Days farm

The Bin at No Bad Days farm is a newly constructed grain bin. As you walk in checkout the beautiful craftsmanship on the ceiling! There is a loft upstairs where you will find a king size bed. There is also an oversized chair that converts to a small bed as well. Main floor has a sofa sleeper for two. There is a kitchenette and full bath. We know you will enjoy the rustic look of this unique property. We are 5 minutes from Lithia Springs Marina and we have room to park a boat!

Peaceful Cabin Retreat

Located on 40 acres of secluded tranquility. It's rustic but it's not roughing it. Enjoy the view from the spacious deck overlooking rolling hills of timber, native grasslands and a large creek. Abundant wildlife (deer, turkeys, coyotes, foxes, squirrels, etc.) for viewing and hiking trails to experience the unspoiled habitat. The property is located at the end of an all-season road. You're likely to see absolutely no one except for your family/friends for the entire stay.

Our Dam House

Unbeatable location less than 1/2 mile from the 9th Street boat ramp, 9th Street Beach, and Forest Park. Also ideal for those attending events at the Chautauqua, or Sunken Gardens. Enjoy a king bed & master bath with jacuzzi tub, a loft with a queen bed and a balcony overlooking the lake, and another bedroom with a queen bed overlooking the spacious back yard where deer come to eat. Our cozy living room has a gas fireplace. The driveway can accommodate boat trailers.

Lake Shelbyville Home with a View

Home sits on 62.5 acres next to Lake Shelbyville, one of Illinois largest lakes, overlooking Country Club Cove. Airbnb unit is 40 yards from waters edge with natural walking paths down to the lake. Public boat launches, and 2 parks are 7-10 minutes drive from the property. The north entrance to the Dacey Trail bike and walking paths are 1/4 mile from the property entrance. Horseback riding on the property is allowed with prior approval only.