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.

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 Hideaway at Howard Farms

Welcome to your private 15-acre escape: where peace, wildlife, and comfort come together. This 2-bed, 2-bath upper unit sleeps 5-6 people with a queen master and a full-over-full bunk room. Mornings bring deer right through the yard, and evenings are perfect for stargazing on the new deck. Hunters will love staying during Illinois deer season. Whether you’re here to hunt in Pike County, watch the wildlife, or simply relax in the quiet countryside down a gravel road, this retreat is for you.

Beautiful Secluded Home With a breathtaking view

Long hidden driveway up to the ultimate private getaway. Beautiful house on six acres with panoramic views of the Illinois River valley, and plenty of space inside and out. Wake up to a breathtaking sunrise from the deck, and feel the serenity as the barges pass by. As evening comes to a close, enjoy a drink and some s’mores by the fire pit and take in the tranquility of this country setting. Seriously, do yourself a favor and spend some time at this quiet, peaceful, one of a kind property!

Scenic 3 bedroom Wildlife Retreat

Relax with the whole family at this peaceful place to stay. This rustic retreat is located on the Illinois river and adjacent to the 5,255 acre National Wildlife Refuge. Whether you fish, watch wildlife from the back deck, relax by firepit or go duck hunting on the bay, you are sure to enjoy this peaceful stay with your family and friends. Wildlife includes bald eagles, whitetail deer, fox, herons, egrets and over 100 species of songbirds. Native prairie trails adjacent to property as well.

Audrey's Abode

Audrey’s Abode is just the place you have been looking for to relax and reconnect with family, friends, nature and a simpler time. Located on a 7 acre hobby farm just south of Jacksonville, Illinois (30 minutes west of Springfield), Audrey’s Abode is a fully restored historic log cabin with all the modern amenities for a comfortable getaway. Need additional space? Check out our other listing next door - Bunkhouse Seventy-Four. Pets are welcome but we charge a $35 pet cleaning fee.

Pike County Haven: Retro Loft

Welcome to our spacious loft studio, nestled in the heart of downtown Pittsfield. Located directly above our family-owned restaurant, you'll experience the perfect blend of comfort and convenience during your stay. The fully equipped kitchen invites you to whip up your favorite meals, while the cozy queen memory foam beds promise a restful night's sleep. Book your stay with us today and discover the magic of downtown living in Pittsfield. We can't wait to welcome you!

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.

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.

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 Yellow Rose Historic Home

This cozy home is 8 blocks to the Mississippi. Beautiful overlooks, nice restaurants, historic homes. A short drive to Two Rivers Marina, the SLU Lay Center Sculpture Park, Hopewell Winery, Ted Shanks Conservation Area, Clarksville Apple Shed. 30 min. to Hannibal, MO - home of Mark Twain. 45 min. to Mark Twain Lake. 90 min. to St Louis. Plenty of sight-seeing, hunting, fishing, boating in the area. Fur babies are welcome.

Cozy Cottage 405

Welcome to this charming, newly remodeled, two bedroom home nestled in a quiet, safe, small town neighborhood. Enjoy the convenience of easy access to local shops and employers. Whether you’re here for work, hunting or just visiting the area, everything you need is just minutes away. Inside you’ll find an open living space, two bedrooms and a dedicated laundry room. High-speed fiber Internet is included.