Holiday rentals in Macoupin County

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 Cabin

Make some memories at this family-friendly cozy cabin. Enjoy the lake life views. Main level is ADA friendly with no steps and a low slope ramp, deck is all one level and wraps 3 sides of the cabin. Master bedroom is located on the main level with a king bed and adjoining bathroom with a low threshold shower as well as a full kitchen dining and living room. Two rooms located upstairs with queen beds and a jack and Jill bathroom with tub shower. Sorry but the cabin is no pets.

Relaxing Fishing Cabin

Relax at this peaceful cozy cabin on Ka-Ho Village Lake, situated just a few miles off historic Route 66. Lake is stocked with Crappie, Bluegill, Catfish and bass for your fishing pleasure, or just sit on the deck by the water and relax. Centrally located on dead end cul-de sac wholly owned by host. 30 minutes to Litchfield Lake Lou Yeager Less then 1 hour to Madison, Il Worldwide Technology Raceway and Tri City Raceway. Less then 1 hour to Springfield, IL or Grafton, IL

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.

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

country living

enjoy out door living in the country. watch longhorn cattle from back yard, take hikes, ride bicycles, provided, watch stars at night while roasting s'mores over bonfire. make 1 breakfast with longhorn breakfast sausage. spend a peaceful weekend together away from the city. no phone (service is available if u still want technology), no wifi. decompress away from technology. please read all sections. Also, we live on the property in case you have questions

Sip & Stay Vineyard Getaway

Nestled on a working winery, this spacious retreat offers room for everyone to relax and reconnect. Wake up to vineyard views, and gather around the fire pit at night to watch the stars come out. With generous indoor and outdoor spaces, it’s perfect for families, friends, or special getaways. Sip local wine at sunset, roast marshmallows, and enjoy the peace of wine country living. Whether you’re celebrating or simply slowing down, this is a perfect choice.

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.

Victorian Home on Rt. 66

Genteel architecture and classic Victorian woodwork define this unique house’s attraction. Inside you’ll find the comfort and hospitality of a bygone era of class and elegance. Located on historic Rt. 66 near the restaurants and shops of Carlinville's charming square. There is a TV in the living room and smart TVs in the bedrooms. Level 2 EV charger. Bring your own NEMA 14-50 compatible cable.and elega