Holiday rentals in Gillespie

Edwardsville Apartment - The Woodland Suite

The apartment in the lower level of the home has recently been renovated, with a walk-out private entrance, a full kitchen & dining area, full bath, bedroom and a cozy living space. Situated just 35 minutes from downtown St Louis, in the safe and affluent community of Edwardsville, this property sits in a quiet cul de sac on a wooded lot right in the heart of the city. We are just a few minutes from the SIUE campus, Edwardsville HS, & I-270. Coffee/restaurants/shops/parks/trails just 2 min away.

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

Cozy Chicken Cottage

Escape to your own peaceful oasis, where comfort meets tranquility, just steps away from a charming, rustic chicken coop. Immerse yourself in the serene sounds of nature on our tiny farm while you enjoy the fresh air. Start your day with a cup of coffee out on the front porch while you overlook our beautiful pond. Perfect for nature lovers, this peaceful hideaway invites you to unwind, recharge and connect with the rhythms of the country. 35 mins to downtown STL. 15 mins to Edwardsville.

Relaxing Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Cozy Historic Downtown Edwardsville Charmer

Spacious and cozy with hardwood floors throughout. Beautifully restored to its original 1920’s glory. Set up to meet your needs. Clean, uncluttered spaces, full kitchen, Wi-Fi, and the basics for an easy stay. Third bedroom offers office space in addition to bunk beds. Relax on the front porch in this lovely neighborhood. Just a few blocks from main street’s offering of coffee shops, restaurants & entertainment. MCT bus stop across the street for easy access to SIUE & St. Louis.

The Carlinville Sunset Bungalow

Escape to this charming 3-bedroom, 2-bathroom retreat nestled in the heart of historic Carlinville, Illinois. This beautifully renovated home, with its classic bungalow architecture and cozy interior, is the perfect base for exploring the town's rich history and stunning natural beauty. Perfect for families, groups of friends, bridal parties, or work trips. Inside, you’ll find a fully equipped kitchen, laundry facilities, and all the amenities you need for a memorable stay.

Bunkhouse Seventy-Four

Once used by seasonal farm labor in the 1930s, Bunkhouse Seventy-Four is a fully restored historic bunkhouse with all the modern amenities for a comfortable getaway. Perfect for couples, it features a full kitchen, bath, queen bed, a spacious porch, beautiful antique stained glass windows, a private outdoor soaking tub (Apr-Nov) on a 7 acre hobby farm. Also check out our listing, Audrey’s Abode, which is next door. Pets are welcome but we charge a $25 pet cleaning fee.

Cozy Home on College Ave

Welcome to our adorable two-bedroom home in the heart of Greenville! Nestled less than half a mile from Greenville University, this cozy retreat offers easy access to 1-70 and Greenville Square. Skip the traditional hotel and enjoy the comfort of a simple home at an affordable rate. With St. Louis just under an hour away, you'll experience the perfect blend of charm, convenience, and proximity to local attractions. Book now for a delightful stay in this inviting space!

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

ThE HiDeAwAy

You’ll be surprised by what’s inside! We’ve designed this space to be more than just a place to stay — it’s an experience, because isn’t that what life’s all about? Perfectly located just two blocks from the town square and only steps from the iconic Million Dollar Courthouse, you’ll also be close to great restaurants and shops. Whether you’re visiting for family, business, or a well-deserved getaway, we hope your stay with us creates lasting memories.

The Campground House

Escape to a private retreat just an hour from St. Louis! Our charming getaway offers a peaceful, country atmosphere where you can relax and unwind or dive into nature. Need more space or a unique experience? Check out our sister property, Timberline Ridge - Tiny Piney! Perfect for additional accommodations or a unique change of scenery, Tiny Piney offers cozy and rustic charm that complements your stay at The Campground House.

Harrison House; PETS WELCOME; FENCED YARD

The Harrison House is a beautifully decorated 2-bedroom house that is in a safe neighborhood. WE ARE PET FRIENDLY. The beds are 12” queen memory foam. All the furnishings are new or nearly new. It has a fenced in backyard. KIDS ARE WELCOME. There is a back deck. There is no cable. There is 100 meg wireless internet. There is a ring camera on the porch. You will hear trains. Two tracks run thru middle of town