Vacation rentals in Shelby

Technicolor River Retreat just outside of Chicago!

Escape the city hustle for a chic retreat on the serene Kankakee River. Our vibrant vacation home, just a stone's throw from Chicago & the Dunes, is a haven for groups & families. Revel in the quirky selfie walls, unwind by the fire pit, or fish off the private dock. Every corner is a conversation starter, from the colorful murals to the luxurious balcony. With high-end amenities and space for six, it's the perfect spot for a lovely reset. Book this incredible home for an unforgettable getaway!

Location · Family · Condition

100 ACRES w/ Private Lake Retro Riverside A-Frame

Nature abounds on this nearly 100 acre riverside estate, a Mecca for outdoorsmen teaming with wildlife across the wooded acreage and 25 acre PRIVATE LAKE. Highlighted by the custom hand hewn timber A Framed retro home with so many architectural nuances. Miles of riding trails for hiking, moto, and equestrian enthusiasts await. Over 2,250 ft of river frontage on the Grand Kankakee River ensures max privacy. Less than 4 miles from IL/IN border and 1 hour from downtown Chicago. Relax unplug unwind

Value · Family · Cleanliness

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Family · Value · Air conditioning

Riverfront Escape: Modern Comfort in Historic Home

Experience riverfront charm in this beautifully remodeled 4BR, 2300ft² historic home on nearly an acre with stunning Kankakee River views. Relax on two spacious patios, watch wildlife, or launch your boat from the private ramp. Just 1 mile from local dining, coffee shops, and bars. This serene retreat offers all the comforts of home. Conveniently located 50 miles from Chicago and only 10 miles from 315 Sports Park and Diamond Point. Perfect for a peaceful family getaway—book your stay today!

Family · Value · Indoor spaces

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

Location · Value · Accuracy

Quiet Farmhouse Retreat

Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

Family · Value · Comfort

Lake front home on the hill.

Please note: Effective September 15, 2026 AIRBNB has pushed their service fees and combined them with our rental fees. I did not raise my prices. They call it simplifying. I called this chaotic and unfair. Hello. Our house is available so that people can enjoy life. Fish, swim, or just hang out on the private pier, (Shared by owner). Beautiful sunsets. House has a large covered deck. Inside you will find a tastefully furnished house with all the comforts of home. TVs in all the rooms.

Location · Value · Air conditioning

The Loft at Virgie

You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

Family · Value · Getting around

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Value · Family · Quiet

Home of 1888

Conveniently located 6 1/2 miles from I-65 between the Lowell and Roselawn exits and 6 miles from Sandy Pines Golf course & The Pavilion. This fully updated place has everything to feel right at home. The kitchen is provided with everything you need to prepare a meal. Plenty of places to eat out are just down the street. A 43" Samsung smart TV with Sling TV and Paramount Plus. When it's time to rest you'll do so on a brand new Nectar memory foam beds.

Family · Value · Accuracy

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Location · Family · Wifi

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Wood fireplaces (winter only!)

Location · Value · Hiking