Vacation rentals in South Wilmington

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Top-rated vacation rentals in South Wilmington

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Top guest favorite

Apartment in Bourbonnais

4.97 out of 5 average rating, 37 reviews

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

Top guest favorite

A serene bedroom is highlighted by a large tufted bed with decorative pillows and a warm throw. Natural light filters through elegant curtains at the windows. A stylish chandelier and a decorative mirror above a contemporary dresser enhance the chic ambiance, complemented by soft wall colors and textured accents.

Apartment in Fairbury

5 out of 5 average rating, 359 reviews

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! ❤️

Guest favorite

The kitchen area features a spacious island with seating, adorned with a 'WELCOME' sign and sunflowers. Cabinets in varying shades of grey and green line the walls. A full-size refrigerator, microwave, and stove are visible, alongside organized kitchen essentials and decorative elements.

Apartment in Marseilles

4.86 out of 5 average rating, 305 reviews

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.

Guest favorite

A welcoming porch area features a green and beige exterior with a door leading into the loft. Decorative pumpkins and flowers are arranged on hay bales, complemented by a rustic chair. Surrounding trees provide a natural backdrop.

Apartment in Chebanse

4.95 out of 5 average rating, 655 reviews

Cathy's Little Farm Loft

Cathy's Little Farm loft is a 500 sq ft apartment inside a storage barn on a wooded country acre. Fully appointed two story space offers peace and quiet. It is located close to I57, Walmart, Community College, Airport, Fair Grounds, National Guard Training Center, 15 minutes from Olivet, 60 miles south of Chicago. King size bed and twin size sofa sleeper upstairs, full size sleeper sofa in living room. Well equipped full size kitchen and laundry. Large lawn, gardens, and chickens to enjoy.

Top guest favorite

A comfortable living area features a large smart TV mounted on the wall, providing a focal point for entertainment. Two inviting armchairs are positioned near a light-colored couch, and a ceiling fan offers overhead circulation. A small coffee table rests on a patterned area rug.

Home in Bourbonnais

4.96 out of 5 average rating, 345 reviews

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.

Top guest favorite

Home in Manteno

5 out of 5 average rating, 11 reviews

Lakeview Estate

Welcome to Lakeview Estate, a charming 3BR, 2.5BA home on Manteno’s Little Lake with stunning lakefront views and direct water access. Enjoy a cozy loft for games or movies, a firepit for s’mores under the stars, and a kayak launch for lake adventures. Just a short walk to downtown for dining, cafés, ice cream, and fun for all ages. Perfect for families, an adult getaway, remote workers, or solo travelers looking to unwind. We can't wait to welcome you to your home away from home!

Guest favorite

A comfortable living area features a spacious sofa with neutral-toned cushions. A glass coffee table sits atop a decorative rug, and wooden shelves display books. Natural light enters through window treatments, complemented by patterned curtains and a floor lamp.

Cottage in Wilmington

4.92 out of 5 average rating, 164 reviews

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.

Top guest favorite

A bright kitchen is furnished with white cabinetry and a light-colored countertop. Modern appliances, including a microwave and an oven, are positioned for convenience. Natural light enters through the window, complemented by decorative elements on the wall and counter for a welcoming touch.

Home in Ottawa

4.93 out of 5 average rating, 161 reviews

"You're invited" Suitcase Required

The whole group will enjoy easy access to everything from this centrally located place. Head to our many state parks, take a boat ride down the Illinois River, be adventurous and skydive at Skydive Chicago and the list goes on. This two-bedroom 1 bath house welcomes you with all the amenities to feel right at home. Sleeps 3 adults comfortably. (1-Queen Bed and 1 full size bed) It has a fully stocked kitchen. washer/dryer and outdoor seating/dining.

Top guest favorite

A gathering area by the water features five comfortable chairs arranged around a rustic stone fire pit. The lush green lawn extends toward the river, with trees providing a backdrop against a sunset sky dotted with soft clouds.

Home in Wilmington

4.97 out of 5 average rating, 71 reviews

Waterfront dog friendly 3 bedroom home w/game room

Eagle’s Hideaway is a secluded waterfront getaway just an hour outside of Chicago, a mile from historic Route 66. Open concept, 3 bedroom home with incredible views of the Kanakee River. Fully stocked kitchen, full bathroom and laundry room with large capacity washer and dryer. The home has laminate and stone flooring and is designed so your dog can be included in your getaway in a worry free, comfortable environment. High speed internet.

Guest favorite

An open studio layout features exposed brick walls and original tin ceilings. A cozy seating area includes a green couch and a round wooden table. A spacious bed with light green bedding is positioned against the far wall, while natural light filters through the window, complemented by dark green curtains.

Apartment in Kankakee

4.89 out of 5 average rating, 70 reviews

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!

Top guest favorite

A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.

Guest suite in Naperville

4.95 out of 5 average rating, 466 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Top guest favorite

The spacious studio features an open floor plan, highlighted by a comfortable bed with plaid bedding and a vibrant area rug. A kitchen with modern appliances is visible to one side, while a cozy seating area includes a coffee table and soft couch. Wall art adds a touch of character.

Apartment in Wilmington

4.91 out of 5 average rating, 82 reviews

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!