Holiday rentals in Shelby

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

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

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!

UncleLarrysLakePlace HotTubKayaksPingPong

A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

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!

Tiny Home on Organic Veggie Farm

Place yourself right in the beauty of the land and nature in this cozy tiny home at Perkins' Good Earth Farm. The tiny home has a loft bedroom, bathroom with shower and composting toilet, kitchen, sitting area, and deck. You'll be surrounded by organic vegetable fields, 11 acres of woods, walking trails--and within perfect view of both the sunrise and sunset. You'll also have easy access to our farm store where you'll find fresh fruits & veggies, homemade soups & salads and so much more.

Private Riverfront Oasis Guest Studio

Welcome to your private river front retreat! This spacious, fully equipped, private studio guest suite is tucked away on the beautiful Kankakee River (with a view!). Located less than 5 miles from I-57, this hidden gem offers convenience of location as well as peaceful beauty. Relax on the porch, take a dip in the river or chill in the hot tub to pass the time. The guest suite is attached to the main house but boasts its own private keypad entry and a completely private stay.

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is optional . Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area after payment of grounds fees.

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.

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.

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

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.