Vacation rentals in Winchester

Florence Guest House--Loft Unit

ONE DAY ADVANCE BOOKING NOTICE! Upper Loft Unit is the top floor of the guest house. With it's own entrance & deck area, No Interaction (if desired) from the lower unit is possible. Loft Supplies: Living room/kitchen area, private bathroom, large bedroom with 2 twins/1 full bed. Deck with an amazing view of the area. Guests DO HAVE FULL USE of the large yard. Guest House Has: Parking area, two Illinois river lots, electric grill, screened in porch. ALL linens, towels, Bed sheets!!

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.

Farmhouse Loft

Experience the life and hospitality of a quintessential small town - Carrollton, Illinois. A historic community located just off the beaten path, Carrollton convincingly captures the spirit of rural America. Inspired by the peaceful charm of country life, we showcase century-old hardwood floors, exposed brick walls and thoughtful design. Farmhouse Loft is a charming retreat on the historic courthouse square --enjoy life in a loft apartment overlooking the courthouse lawn!

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.

My Little Bungalow on Monroe Street.

My Little Bungalow on Monroe is a family friendly, stylish bungalow that is a welcoming space in a peaceful Beardstown neighborhood. Only two blocks from the city square, the Bungalow on Monroe is within easy walking distance of several local eateries, and festival events held in the city square. This two bedroom home is has one queen bed, three twin beds and a daybed. A washer and dryer, as well as a second shower are available in the basement.

The Bike Flat

Visit historic Winchester and explore what our quaint community has to offer! This stylish place to stay is perfect for a quiet getaway and can accommodate groups thanks to its ample space. You can bring the family or plan a getaway with friends. The flat is located above a newly opened bicycle and coffee shop that also offers craft beers and wine. We hope you will consider choosing our rural accommodations for a trendy and relaxing experience!

The Petersburg Place nestled near downtown

Please enjoy your stay at The Petersburg Place, a cozy 2-bedroom, 1 bathroom home nestled on a neighborhood hillside near downtown Petersburg, Illinois! The house has only three steps required to enter the single-level home, keyless entry, plenty of room to park several vehicles or a boat, a fenced backyard with a deck, full kitchen with cooking essentials, a 55" TV (Amazon Firestick), and Wi-Fi.

Virginia Lake Getaway/Fishing/Hot Tub/Hammock

Welcome to your charming log cabin located in Virginia, IL. This 1-bedroom, 1-bathroom cabin is designed to provide you with rustic comfort, making your stay truly exceptional. Nestled on a bluff overlooking the serene Virginia Lake, this 1850's log cabin combines historic charm with modern luxuries. Set on 80acres of timber and water for you to explore. Hike, kayak, fish or just relax and enjoy!

The Hunter's Cabin, a Rustic Retreat

Take it easy at this Rustic, Unique and Tranquil country getaway. Whether you are here to harvest the bounty of nature or just to get away from the city you are sure to enjoy your stay. I would like to extend a warm welcome to guests of all backgrounds looking to stay at the cabin who agree to treat the cabin with respect and abide by the house rules!