Holiday houses in Pleasant Hill

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.

Historic Loft on Adams

Charming updated loft-style studio in the heart of quaint downtown Pittsfield. Located within walking distance of restaurants, the historic courthouse, and local bars. This private apartment is perfect for weekend getaways, staycations, or even a cozy home base to work from remotely. The view of our Pike County Courthouse from any window is gorgeous and the historic building has so much character, all in a convenient, central location. This second floor loft is completely private.

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 $35 pet cleaning fee.

Home away from Home

A relaxing and inviting home away from home with everything that you need for your stay in Bowling Green. During your stay here you will enjoy the smart TV, free Wi-fi, and washer and dryer. A comfortable night’s sleep is a given with a brand new mattress on all three beds (queen bed and two twin beds). Located on the north side of town, you are less than 1 mile from Wood’s Smoked Meats and Bankhead’s Chocolates. This is an ideal base for your Pike County, MO visit.

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 Humble Hideaway

Escape the hustle and bustle in our charming backyard oasis, just a short walk from Main Street. This private home offers a cozy patio, and all the comforts of home including a fire pit and dining table. The home itself is bright and airy with hardwood floors, and a new central air conditioning. Curl up on the plush sofa and enjoy the flat screen smart TV in the main living area or prepare a meal in the fully equipped kitchen with brand new appliances.

Cozy Townhouse Retreat

Welcome to "Cozy Townhouse Retreat," a beautifully designed new construction multi level townhome offering 3 cozy bedrooms and 2.5 baths. This modern home features high-speed internet, convenient washer and dryer, and outdoor patio with gas grill and seating area, ideal for entertaining or relaxing. With a one-car garage and off-street parking, convenience is at your doorstep. Experience comfort, style, and modern amenities all in one place

Modern-Rustic Cabin, Nature Inspired

Set in wooded acres, the Hillview House is a studio cabin that blends modern comfort with natural charm—from the handmade coffee table and live-edge shelving to the crisp white quartz countertops. Every detail is designed to feel both elevated and grounded, like nature brought indoors. Whether you’re sipping coffee on the porch or curling up after a day of work, this space was made for slowing down.

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!

Pere Ridge Tree Escape with private hot tub

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.

Dairy Farm Stay • Fresh Eggs & Milk • Peaceful 2BR

Escape to a quiet dairy farm where you can wake up to cows, calves, fresh eggs, and peaceful country views. Our cozy 2-bedroom farmhouse sleeps up to 7 and offers full kitchen, WiFi, and plenty of trailer parking. Perfect for families, hunters, workers, or anyone needing a quiet getaway Easy day trips to Bowling Green, Wentzville, or St. Louis

Full Country Home Pittsfield, Illinois

Relax with the whole family at this peaceful place to stay. WE HAVE WIFI and Smart Tv in the living room and back bedroom Great place for hunters,jeepers,rock climbers, 10 minutes to Pittsfield,Illinois where there are many restaurants, shopping and historic attractions. Located between New Hartford and Summer Hill, Illinois on US Hwy 54