Holiday houses in Shelby County

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Top-rated holiday rentals in Shelby County

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Top Guest favourite
Home in Sullivan
4.99 out of 5 average rating, 111 reviews

Game Room | Hot Tub | Fire Pit @ Lake Shelbyville

Sitting just a mile outside city limits and minutes to Lake Shelbyville is this beautifully appointed home waiting for guests to enjoy all of its amenities; pool table, fire pit, grilling area, corn hole set, and hot tub. Inside, nothing was held back when it came to decorating this home for a truly relaxing experience. All the amenities of home are here just waiting for you to arrive, relax, and enjoy. We are sure you will rest easy in this boutique style home located at Lake Shelbyville.

Top Guest favourite
Home in Sullivan
5 out of 5 average rating, 48 reviews

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.

Guest favourite
A charming white house with black-framed windows is framed by seasonal foliage. Bright red bushes contrast with the house's exterior, and potted plants are positioned beside the entryway. The inviting red door serves as a focal point, completing the home's welcoming appearance.
Home in Shelbyville
4.95 out of 5 average rating, 58 reviews

909 & Vine Photo Worthy Home With Pool & Hot Tub

Imagine a luxurious location with versatile design capabilities that convert to your needs. Offering accommodations and VIP services that provide you with all the comforts of home, and then some. Experience a private outdoor space to relax poolside, soak in the hot tub, sit by a fire, or take a peaceful stroll through beautiful gardens and lush grounds. For those days where you want to just stay inside, we offer board games, an Xbox One game console, and 5 TV's with streaming capabilities.

Guest favourite
Cabin in Shelbyville
5 out of 5 average rating, 13 reviews

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

Top Guest favourite
Home in Shelbyville
4.98 out of 5 average rating, 90 reviews

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.

Superhost
A spacious living area features two comfortable leather sofas with decorative pillows, arranged around a central coffee table. Large mirrors adorn the wall above the table. Light wood cabinetry and modern appliances are visible in the open kitchen area, enhancing the inviting atmosphere.
Home in Sullivan
4.82 out of 5 average rating, 85 reviews

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.

Guest favourite
The exterior of a spacious villa is presented under a clear blue sky. The building features a welcoming entrance with a covered porch and multiple windows. A gravel pathway leads to the front door, surrounded by well-maintained landscaping and green trees in the background.
Home in Sullivan
4.96 out of 5 average rating, 136 reviews

Lake Shelbyville-Lakeside Villas

Lake Shelbyville is the perfect place to spend your next vacation, reunion, weekend away you name it! Our property offers amenities shared among the villas; fully stocked pond, half basketball court, fire pits, playground, & backs up to a local popular camping ground, just minutes from the lake and marina! Inside our villas are fully equipped kitchens, washer and dryer, free WiFi, smart TVs, fully stocked with starter amenities to get your vacation started without rushing to the store!

Guest favourite
An aerial view showcases the property’s extensive 5 acres, highlighting a large, stocked fishing pond surrounded by manicured grass. Trees line the perimeter, and a spacious area is visible for both parking and outdoor activities, including a pathway leading to additional structures.
Home in Sullivan
5 out of 5 average rating, 14 reviews

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.

Top Guest favourite
The image captures a hot tub on a patio, framed by a wooden pergola. A round table with chairs is positioned nearby, with an expansive view of the sunset over open fields. The warm glow of dusk enhances the tranquil outdoor setting.
Cottage in Sullivan
4.95 out of 5 average rating, 204 reviews

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.

Top Guest favourite
Farm stay in Shelbyville Township
5 out of 5 average rating, 38 reviews

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!

Guest favourite
A spacious living area is highlighted by two white sofas arranged around a round coffee table. A gas fireplace is situated against the wall beneath a wall-mounted television. Large windows allow natural light to fill the room, and a ceiling fan enhances airflow.
Home in Shelbyville
4.94 out of 5 average rating, 36 reviews

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.

Superhost
The view from a deck captures a sunset over a tranquil landscape, featuring a red silo in the background and bare trees lining the horizon. The pasture is visible in the foreground, presenting an expansive, peaceful feeling of the countryside.
Farm stay in Windsor
4.71 out of 5 average rating, 49 reviews

The Horse Hotel. Country living at its finest.

This freshly remodeled apartment is on a 155-acre farm. It’s located close to Lake Shelbyville and Lake Mattoon. There is a tv in every room with new beds. Full kitchen with everything you need. The deck has the best view of the farm. The apartment is above a horse barn and overlooks the property Plenty of parking is available and lots of area to enjoy the outdoors. The peace and quiet of this countryside retreat is something you’ll never forget.

Popular amenities for Shelby County holiday rentals

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