Vacation 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.

The Carlinville Cottage

Whether you're in town to visit family, see the sights, or get away for some well-earned time off, this 3-bedroom, 2-bathroom vacation rental is the perfect place to host your next trip to Illinois! This cottage features a modern interior, a well-equipped kitchen, and a large backyard with plenty of space for kids and pets to run around. Spend your days exploring the nearby historic district of Carlinville and enjoying the surrounding attractions before heading home for a relaxing night in.

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.

Cozy Tiny Home in Woods w/ Firepit & Porch Swing

Need a break? Some time to relax and breathe? Come get away from it all at this TINY HOME in the woods. Roast s'mores around the fire pit, go kayaking on nearby Carlyle Lake, stargaze on the porch swing with a cozy blanket...or just cuddle up and binge watch your favorite shows in front of the fireplace. Fully updated with everything you need: full size washer/dryer, stocked kitchen, smart TVs, wifi, outdoor grill, 2 RV hookups, space to park a boat - conveniently right off of I-70!

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.

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.

Full studio apartment by the best Springfield park

Historic home attic converted to a private 3rd floor apartment, featuring private kitchen and bathroom. Located just two blocks from what many would agree is the best park in Springfield, with a pond, a botanical garden, tennis courts, a playground, and nice roads to run, walk, bike, or skate on. We are also very close to downtown as well as other commercial areas. This space is on the 3rd floor with private access from outdoor stairs and keypad entry.

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

Private, Bluff-Top Cottage Above Mississippi River

This charming, remodeled cottage is conveniently located between Grafton and Alton, IL on top of the bluff, high above the Mississippi River and the Great River Road. This 2 bedroom cottage is in a private, woodland setting perfect for your bird and wildlife viewing. We have seen many eagles, turkey and deer. Although there is not WiFi in the house, there is a WiFI and River viewing area close by.