Vacation rentals in Pittsfield

Container Home GREAT Countryside Views COZY Stay

Singing Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

Oakbrook Akers Lakeside Cabin Retreat

Located in the heart of the country, Oakbrook Akers Cabin is an absolute retreat! Relax on the many porches overlooking the pond, take time to meander to the docks to fish, enjoy s'mores over the stone fire pit or spend the evening at the grilling station in our covered patio. In the winter, tuck yourself away in the cozy cabin complete with a wood burner, having a movie or game night (with popcorn of course)! Built by my father, we hope you cherish your time spent here just as our family has.

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!!

The Spring House!

Enjoy a stylish experience at this centrally-located 1890's farmhouse that has been completely transformed with all of the amenities you want and need. This convenient first floor apartment is located right across from one of Quincy's most iconic and favorite restaurant's, The Abbey! A fabulous space that features keyless entry, beautiful kitchen with quartz counter tops and stainless steel appliances, a wonderful onyx shower and comfortable beds with high end furnishings and lots of extras.

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.

Two Doors Down Loft, Virginia-Lincoln territory!

Located in VIRGINIA, IL-Our fantastic, urban vibed loft sits on the town square across from the town's historical courthouse. We are 30 minutes from Springfield, 15 minutes from Jacksonville and in the middle of Abe Lincoln territory and historical markers. The loft is also surrounded by lovely wineries and wildlife parks. Be sure to thoroughly read our listing to ensure that we'll meet all of your needs in exploring our unique area. Two Doors Down is a hidden gem listed at a super price!

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!

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.

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!

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!

❤️Quincy Quarters 2❤️

Quincy Quarters is a beautifully restored 1880’s Duplex with modern amenities and all the historic charm. This duplex has been home to families for 140 years. Bring your family and your pet and enjoy 140 years of history. Quincy Quarters is close to Oakley Lindsay Center, Blessing Hospital and Quincy University, it is blocks away from South Park and just a couple minutes from downtown Quincy.

Pere Ridge Tree Escape

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a 10 minute drive to Grafton.