Holiday rentals in Le Roy

Monticello Carriage House

This carriage house is located at the back of the property of a 117-year-old historic home 4 blocks from downtown shopping and dining. We're 15 minutes from Allerton Park & Retreat Center, 25 minutes to Champaign and 30 minutes from Decatur. You’ll enjoy the comfy bed, two dining/game spaces, TV area, a small kitchen with cooktop, small refrigerator, microwave, coffee pot and a full bathroom. It is great for a weekend get-away! Come to enjoy Monticello! Same-day bookings-6:30 check-in time

Special - House of Games - Play, Relax, Unwind!

Ready to get your kicks on Route 66? Your group of up to 11 will have a blast playing more games than you’ve ever seen in a vacation home. House of Games lives up to its name with skee ball, ping pong, air hockey, pop-a-shot, foosball, classic game-console room – and more. Guests praise the variety and fun of 10 arcade games. Kiddos love it here, and families cherish spending time playing games together. Relax in the backyard with firepit, grill, hammock. All this – plus free soda + ice cream.

Stunning XL Rustic Modern Escape w/ Arcade & Spa!

Sticks & Stones Rustic Recreation Retreat is a 16+ guest luxury log cabin on the west edge of Bloomington, IL. Secluded in peaceful wooded acreage, yet just minutes from TONS of restaurants, bars, sports & activities! 🎱 HUGE ARCADE CAVE! 🤩🏒⛳️🏀 🫧 Jacuzzi & Sauna 🔥 Fire pit & grill 🥘 Fully stocked kitchen ❤️ Comfy lounge furniture 🛌 6 sleeping areas, 3 full baths 🧼 👑 Dreamy mattresses! 💤 🚿 Endless hot water 🎮 6 TVs & Xbox 🎤 Karaoke! 🎉 🕊️ 4 Beautiful Porches 🌳 Swings & big yard!

The Lexington House on Route 66

A touch of yesterday to experience today. This 3 bedroom, far out home will take you back to the 1960's with its shag carpets, Love beads and it's flower power vibe. This Groovy house with it's park like backyard is just feet from historic route 66 in Lexington Ill. Take the bikes at the house for a ride down the Oldest portion of Route 66 or just relax and enjoy the restaurants, bars and shopping in downtown Lexington . This nostalgic home that sleeps 8 will transport you back in time.

Timber Time in Hudson Hideaway

Looking for a break from the busyness of life, to relax and enjoy nature? Step back in time in this tranquil and rustic home. In a remote location and surrounded by timber, this property is perfect to unwind, enjoy a sunset, and view the stars in a wide-open sky. The large yard allows for all kinds of activities and the circle drive provides easy RV, trailer, and boat access. Located next to Evergreen Lake/Comlara Park, the hiking and biking trails, boat ramp, and beach are just minutes away.

No Fees! - The Chanute - Your Home Base

Located in Rantoul, Illinois, this two bedroom, one bath gem has been lovingly transformed to celebrate the history of Chanute Air Force Base and honor the base's namesake, Octave Chanute. Situated in a quiet neighborhood, THE CHANUTE provides guests with easy access to local highlights such as the Rantoul Sports Complex, B52 BMX track, Gordyville USA, & Flyover Studios, while only requiring a short drive to visit the University of Illinois and other attractions throughout Central Illinois.

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 a week long stay and receive 40% off ❤️

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

Platypus Hills, Lake, Heated Pool, Hot tub,Firepit

This cozy 2-bedroom country house sits on 8 acres, sleeps 4 and overlooks Clinton Lake with amazing views. We offer a hot tub, heated pool, kayaks, 10 miles of hiking, hunting, and horse trails. The boat ramp is located at the end of the driveway and across the street. We are located 30 minutes between Bloomington & Champaign. All guests must be 18+. An additional $50 per person per night over 2. Pool open May-Sept. PLEASE READ THE ENTIRE LISTING TO ENSURE IT MEETS YOUR NEEDS.

Spacious 3-bedroom above historic flower shop

Stay the night at this conveniently located apartment on Mr Lincoln Square in Clinton, IL above historic Grimsley’s Flower Store. Enjoy easy access to dining, shopping, and activities. Get ideal parking for Clinton’s famous Apple and Pork Festival. Outdoor fun is a short drive away at Clinton Lake or Weldon Springs Park. Friends and family can visit in the spacious living room. Multiple tvs, activities, and a dining area for six helps keep the whole family entertained.

J&E Homestead--spacious home in the country!!

Our farm home, situated on 4 acres, is located just 25 minutes from the University of Illinois and Illini sports! I-57, I-74, and I-72 are all close by. The house has a fully furnished large kitchen with a coffee bar. Two living areas provide plenty of space to stretch out. You can finish off your busy day gathering on the patio preparing dinner on the gas or charcoal grills, watching the sun set over the summer grain fields, or roasting marshmallows around the firepit.

The Schoolhouse Cabin - Hot Tub & Game Room!

A charming getaway near the lake and woods of Lake Bloomington in Central, IL. Originally built as a schoolhouse one hundred years ago, this cabin has character and unique features for days! The comfortable and eye catching furnishings and decor, along with great amenities, big and small, you’ll find the Schoolhouse cabin to be just what you need for a relaxing getaway. Enjoy the hot tub, heated game room outdoor bed or the multiple reading nooks.