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.

Little House in the Hollow

Private Hot Tub • Pet-Friendly • Walk to Mark Twain Cave & Winery • Near Downtown Hannibal Relax in this PRIVATE cozy retreat perfect for families, couples, or business trips. Enjoy a private hot tub, fenced yard, fire pit, BBQ, fast Wi-Fi, full kitchen, and self check-in. Walk to the Caves, Winery, Trolley & MT Live Show; downtown is 2 miles away. Explore, unwind, and enjoy a comfortable stay close to Hannibal’s top attractions. Only Airbnb to offer a discount to the 4 ticketed attractions!

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!

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.

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.

Florence Guest House

This 1,200 sq. ft. PRIVATE BOOK is a 175 year old building that Abe Lincoln stayed in. Central A/C, Forced air heat, Two decks (one overlooking the Illinois River), burn pit, outside grill, fully equipped kitchen, screened in porch, ample parking, access to the Illinois River/ boat ramp near, tie up on Our Private Lots! NOTE: RECENTLY HAD Guests' wanting to "JUST GET AWAY" for A Time!!! PRIVATE TIME ALONE, Guaranteed!!! NEW KEURIG; BRING YOUR OWN K-CUPS!!!***

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.

Dome View Loft

Dome View Loft is a unique unit with comfort and spacious for your group. There is two bedrooms with each offering a queen bed. We own a Cafe with full menu right below for your convenience. There is a washer and dryer if needed. The view of our historic Courthouse is beautiful. Come and enjoy the quiet atmosphere with free parking. This location is within walking distance for downtown coffee shops and Book Store.

The Milkhouse

Get away from it all when you stay under the stars, commune with the cows and observe wildlife. See a working ranch and learn about farm life from us. Stay in a climate controlled modern farm house with lots of extras. Highway access and solid driveway to the farm house. Explore the hills, hollers and creeks. Close to Hannibal Mo and Mark Twain Lake among other local attractions.