Holiday rentals in Shelbyville

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

Shelbyville- Fish, boat, grill, chill, pets, relax

Welcome to REST ASHORED where you can be as restful or as active as you please! Boat around Lake Shelbyville in the morning and return home to play a 9-hole round of golf on the Timberlake course in the afternoon. The boat launch is only a mile away so you won't need much leeway to make your tee time. Or to restock the cooler, for that matter. Enjoy dinner in a full kitchen and watch TV on your large screen TV. Wind-down watching the sunset over the golf course from your back deck.

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.

Vintage Victorian | Lake Shelbyville Getaway

Nestled just 1 mile 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.

Lakefront Cottage • Dock, Kayaks, Fire Pit & Beach

Welcome! Imagine waking up ten steps from the water, kayak paddles already calling your name. The Lake House on Lake Sara puts you right at the edge of the lake — with four kayaks, a crackling fire pit, and a sunlit enclosed porch to come home to. The Lake House is located just a short walk to the Beach, Pinky’s , The Rusty Reel Bar (below Pinky’s) and The Marina. The beach offers a beautiful playground, pavilions, exercise equipment, pickleball courts and a frisbee golf course!

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!

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.

The Little Homestead Haven

Welcome to the Little Homestead Haven! Whether you are looking for an anniversary getaway or if you are traveling through the area and looking for a relaxing spot to rest, you will thoroughly enjoy your stay here. Relax and take a soak in the hot tub, while the soothing jets work the tension out of your muscles. It is located less than 2 miles east of Arcola and just off Interstate 57 on Rt. 133, 30 minutes to Champaign airport and right outside of Amish country.

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.