Vacation rentals in Gillespie

The State Street Loft | Small Town Charm

Welcome to your spacious 1,700 SF home away from home in the heart of Downtown Litchfield! This 2nd floor loft blends modern updates with old-town charm, featuring 3 comfy bedrooms, 1.5 bathrooms, and soaring ceilings that create an airy, open feel. Enjoy a space with plush seating, high-speed internet, and a workspace - perfect for both relaxation and work. Whether you're here for a weekend escape or an extended stay, this downtown loft is the perfect mix of comfort, style, and convenience.

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.

Hilltop Ranch Home on 25 acres bathed in starlight

Welcome to our Hilltop Ranch Home! You will find a relaxing getaway for your entire family or several couples. There is 1800 sq ft on the first floor including a master bedroom with ensuite bathroom boasting a jacuzzi tub, a fully stocked kitchen, gas fireplace, and an attached 2-car garage. In the walkout basement, there is a fourth bedroom, full bath and a TV area. A patio adjoining the dining room, a charcoal grill, and full-size hot tub-all perfect for entertaining your whole group.

Wooded 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.

The Loft

Enjoy a peaceful stay in “Our Nest” loft that is nestled in a pretty neighborhood and within walking distance of two restaurants. Within 15 miles, you can experience several small towns and cities which have so many attractions, recreational activities, restaurants, and bars. “Our Nest” loft is 45 minutes from St.Louis and Lambert Airport . We are also 30 minutes to the beautiful Great River Road. You can visit the city and return to the peace and quiet of our small town

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.

Lake House off Route 66

Lake House Cabin is the best property in the area and offers a 2 acre lot at the end of a peninsula off Route 66. *Includes private lake access with fishing dock. *House has a fenced in dog area with doggie door. *Swimming, paddle boat and fishing allowed* *Crappie, bass bluegill, blue cat and channel cat. *Smoking allowed outside* *Pets 2 max *Crate pets when left alone. *4 person paddle boat *4 Guests Max including kids. *Wifi *No parties*

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

Downtown Hillsboro Loft

Two bedroom loft space in downtown Hillsboro located above a book and game store and next to a coffee shop and candy store! It’s also walking distance from a brewery, movie theater, live theater, ice cream shop and several local retail stores. The living space displays works of local artisans to complement the hint of mid-century style. With 1200 ft. of living space you will have room for everyone!