Holiday rentals in Livingston County

4.9 out of 5 average rating, 107 reviews

Work hard. Play harder. You deserve it.

GuestWork is a local Property Management Company and we operate nearly all of the AirBnB's in our community. We have units designed for weekend getaways, temporary housing for local displaced residents, mid-term stays for local work travelers and go to great lengths to accommodate guests in the area to visit family and friends in our perfect little town. Please feel free to complete an inquiry and tell us exactly what you are looking for and let us help align you with the perfect unit in your

5 out of 5 average rating, 362 reviews

Flat in Fairbury

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! ❤️

4.92 out of 5 average rating, 172 reviews

Home in Lexington

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.

Apartment in Pontiac

4.78 out of 5 average rating, 9 reviews

Rooks Creek Acres

Escape to Rooks Creek Acres, a charming retreat nestled in the heart of Rooks Creek Township. This cozy space, adjacent to a picturesque barn, is ideal for individuals, couples, or small families seeking a serene getaway. The rental features two inviting bedrooms, one conveniently located on the ground floor with an ensuite bathroom, and another in a quaint upstairs loft, offering a unique sleeping experience. Immerse yourself in tranquility and comfort at this delightful countryside escape.

4.88 out of 5 average rating, 43 reviews

Flat in Fairbury

Downtown Fairbury Building

Centrally located! You're just steps away from some of the great shops, bars, & restaurants that downtown Fairbury has to offer. Dave's supermarket is also only a minutes walk away. And for you race fans, the Fairbury Speedway is only a 3 minute drive or an 8 minute walk away. The building has 1 bedroom with a queen bed. Living room has a long sofa & pull-out loveseat that sleep 1 each. It has a 1/2 bath with a toilet, sink, & washer/dryer in it. The only shower is located in the bedroom.

4.99 out of 5 average rating, 123 reviews

Bungalow in Pontiac

Lucky 7s Bungalow w/Hot Tub

It’s your lucky day! Welcome to this charming south side bungalow. Whether you are in town visiting family or friends, working remotely, or playing tourist, the Lucky 7s is the perfect place to call home during your stay in Pontiac. Our home is designed with modern touches and your family in mind. Gather around the table playing games while the chef of your group cooks up something delicious in the fully stocked kitchen. Afterwards, unwind and enjoy the hot tub in the private backyard.

Superhost

Guest house in Lexington

New place to stay

Pool House on Castle Property!

This stunning pool house is nestled on 42-acre estate, offering a blend of modern and serene beauty. You'll be staying on a property known as "the castle," a historical landmark. The pool house offers contemporary design with modern furnishings. The kitchen boasts Viking appliances, perfect for whipping up a gourmet meal or a snack. Step outside and unwind in the soothing hot tub under the stars or enjoy use of the full-sized court for a game of tennis, pickleball, or basketball.

4.88 out of 5 average rating, 56 reviews

Home in Hudson

Rocky’s Retreat & Lakeside Serenity

Welcome to our breathtaking lakeside retreat in central Illinois! This spacious 4-bedroom haven accommodates up to 12 guests, offering the perfect escape for families or friends. Enjoy the seasonal pool, and take in stunning lake views. With 3 full bathrooms and 2 half baths, there's room for everyone to refresh and recharge. Cozy up by the fire pit or explore nearby attractions. Create lasting memories at this idyllic getaway—book your stay today!

5 out of 5 average rating, 34 reviews

Route 66, 5+ Acres with a pool, Sleeps 16

Right off the legendary Route 66 in Pontiac, IL, our Airbnb home rolls out the red carpet for events ranging from birthdays to uproarious reunions, all while rocking a mix of chic and cheek. With room to comfortably entertain, whether they’re cutting a rug or just cutting into the buffet, this spot has your big bash covered. Imagine your event set against a backdrop of meticulously groomed landscapes that even the garden gnomes would envy.

4.94 out of 5 average rating, 273 reviews

Baby, I just need a little getaway.......

Come spend a night, or an entire wknd out in the cold...in a luxury hot tub! Enjoy a spacious, 2 bdrm, two BR pet and 420 friendly brick ranch with tasteful decor on a corner lot. W/D, full access garage and screened in porch with fenced in yard. House fits 4 comfortably, but hot tub fits 7. Let me know if we need to discuss sleeping arrangements for more than 4 guests. You simply won't find a more accommodating host on the platform.

4.8 out of 5 average rating, 61 reviews

Flat in Lexington

Enjoy Horse life

Take it easy at this unique and tranquil getaway. 15 easy miles from Bloomington Normal, this one bedroom apartment on a horse farm gives you the opportunity to experience country life. Less then 3 miles to downtown Lexington where you can experience unique shops, a local brewery, and several restaurants. A short 5 miles the other direction will take you to Lake Bloomington. Ample parking if you are bringing a boat. Wi-Fi included.