Holiday rentals in South Wilmington

Upside Inn

What are The Upsides you ask? Sparkling clean, tastefully decorated, spacious, and convenient location to name a few. An ideal base from which to explore and enjoy local/Chicago, this 1 bed/1 bath apartment (ground level duplex/no stairs) has everything you need for a supremely comfortable stay. Perfect for pleasure or work-related travel. Upside Inn aims to please with a dedicated work space and modern amenities. 10 min to Riverside Medical and ONU, 50 min to Midway Airport & 5 min to CSL

Chic Retreat Small Town Charm, City Sophistication

The ultimate escape, at Wells on Main Guesthouse & Gatherings where small-town charm meets big-city sophistication. Whether it’s a romantic getaway, girls’ weekend, or just time to recharge, our elegant retreat has you covered. Couples can cozy up in dreamy spaces and create lasting memories. Gather your best friends for laughter, wine, and chic relaxation in a stylish setting. With local charm and upscale comfort, every moment feels magical. Book now and discover your home away from home! ❤️

Dog Approved Country Suite

This floor of my home is all yours! Non-shared, non-smoking studio, fully fenced back yard. Please choose my home for yourself, not just your dog; enjoy a full kitchen & appliances, 1 full size futon bed, basic tv, laundry & bath w/free parking. It’s peaceful living on a septic w/well water. Welcome to the country! Clean yes, but lived in & loved. Limited WiFi-no streaming. Weekly & monthly discounts. Approx 5 miles to I80 & 21 miles to Starved Rock. LOOK AT A MAP I can’t change my location.

Family & Pet Friendly, No Stairs,10min to Rock Run

Modern, Ranch style home, No Stairs Retreat, Near New Joliet Hollywood Casino (Rock Run Collection) and Plainfield. Pet Friendly. ★ King bed + ensuite ★ open concept kitchens ★ 3 large Smart TVs ★ Dedicated Office Space+Desk + Monitor ★ 2 Door Garage LOCATION **** LOCATION***LOCATION ★ Rock Run Collection - 10 minutes ★Starved Rock State Park - 1 hour Located within 15-20 minutes of: ★Haley Mansion ★Joliet Junior College ★Harrah’s Casino ★Downtown Plainfield ★Rialto Square Theater

Bourbonnais/ Sweet home a short walk to O.N.U.

You will love this 2 bedroom home with 3 large smart TV's, one 65" in the living room and a 55" smart TV in each bedroom. The master bedroom has a super comfy king size bed with king size hotel pillows and the second bedroom has a super comfy queen bed. The kitchen is complete with all the cooking & eating utensils that you need during your stay. There is a Keurig coffee pot with complimentary coffee & cream & sugars. There also a drip coffee maker with filters that we supply.

Get Your Kicks in Our Cozy Cottage Near Route 66

Enjoy all the comforts of home when you have to be away. Our fully furnished cottage is located 4 miles from Rt 53 / Historic Rt 66 and just blocks from the Kankakee River. Just 5 minutes to "downtown" Wilmington featuring restaurants, a wine bar, a local brewery, and multiple antique stores. ✧ Easy access to everything that Joliet has to offer just 20 miles away, including the Autobahn and Route 66 Raceway. ✧ 7 miles to easily access I55 for a quick ride into Chicago.

Boho - Chic Retreat #3

Welcome to your Boho Chic Retreat in Kankakee! This cozy studio features charming exposed brick walls and original tin ceilings, blending vintage character with modern amenities. Enjoy a fully equipped, modern kitchen and a luxurious walk-in shower. Located within walking distance to restaurants, coffee shops, bars, and entertainment, you'll have everything you need at your fingertips. Book now for a unique and stylish stay!

Boho Haven • 2 King Beds • Washer/Dryer • Trails

✤Boho Haven✤ is a cozy, boho inspired 2BR first floor apartment with fast Wi-Fi, 2 king beds, full kitchen, and a private entrance. It’s perfect for couples, families, or business travelers visiting Kankakee. Quiet area close to shops, restaurants, trails, the river and top spots: ✶ 1.7 Miles to Olivet Nazarene University ✶ 1.3 Miles to Riverside Medical Center ✶ 1.2 Miles to Perry Farm Park ✶ 55 Miles to Midway Airport

Downtown Modern Studio by Route 66

Located right in downtown Wilmington, our Studio66 is walking distance to great food and nightlife/bars, as well as the beautiful Kankakee river. No matter if you're traveling Route 66, visiting family in town, or staying locally for work, Studio66 is a fun and convenient place to stay. You'll feel right at home right off "The Mother Road" staying at our spacious studio!