Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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Top guest favorite

The exterior of the cabin is displayed at dusk, showcasing a welcoming porch with seating. Soft lighting highlights the entrance, while ample greenery surrounds the structure. Gravel pathways lead to the cabin, enhancing the naturally serene setting.

Cabin in Winchester

4.96 out of 5 average rating, 158 reviews

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.

Top guest favorite

A stone fire pit is surrounded by a circular area made of flat stones, set on gravel. A stack of firewood is nearby, with a serene lake visible in the background, framed by trees and an overcast sky.

Cabin in Camp Point

4.99 out of 5 average rating, 136 reviews

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 lake, 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.

Top guest favorite

Two deer, one adult and one fawn, are seen standing in a grassy area beside a wooden fence. The lush greenery surrounding them emphasizes their natural habitat, while the soft sunlight highlights the gentle features of the deer.

Guesthouse in Jerseyville

4.97 out of 5 average rating, 135 reviews

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.

Top guest favorite

A collection of decorative items rests atop wooden cabinets. Two ceramic roosters and a chicken figurine are positioned on either side of a vintage-style 'Farm Fresh' sign, which features an image of a rooster. The warm wood tones enhance the rustic decor.

Home in Winchester

4.92 out of 5 average rating, 134 reviews

Winchester Guest Cottage

The Winchester Guest Cottage is a chance to experience the past while still enjoying the comforts of modern living. Guest will appreciate the living history of this mid 1800s home with much of its original architecture still intact. Enjoy the natural light from the tall windows while peering out through much of the original wavy glass. Most of the homes original wood work, doors and fireplace mantel are still there as they were in the 1800s. The floors were repurposed from WHS in the 1950s.

Top guest favorite

A historical red brick courthouse is showcased with a symmetrical façade. Tall windows with arched tops are arranged in groups, and an American flag is displayed on the front. Green trees and a well-maintained lawn are visible in front of the building.

Loft in Virginia

4.94 out of 5 average rating, 160 reviews

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!

Guest favorite

A table is covered with a patterned tablecloth, featuring a stylish UV lamp. The lamp emits a blue light and is positioned next to a decorative plant, enhancing the table's setup in the inviting space.

Guest suite in Pittsfield

4.82 out of 5 average rating, 132 reviews

Florence Guest House--Loft Unit

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 (Fitted Bed spreads). 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, charcoal grill, screened in porch. ALL linens, towels, Bed sheets!!

Top guest favorite

Townhouse in Murrayville

4.98 out of 5 average rating, 304 reviews

Peace on the Prairie Too - Tiny House

Need a break from Politics? Peace on the Prairie accepts all guests for who they are rather than what some might wish them to be. Whether it’s a business trip, romantic time together with your significant other, a family vacation, a girl's time away, a secluded spot to work on your music, writing, art, star gazing, or a reconnection with nature, you'll find your inspiration and renewal in this natural rural setting of 23 acres of restored prairie, timber, and wetlands?

Top guest favorite

An antique cast iron soaking tub is situated on a wooden deck, enclosed by a yellow picket fence and decorative curtains. A wooden shelf is mounted on the fence, with natural elements visible in the background adding to the peaceful outdoor setting.

Cabin in Jacksonville

4.97 out of 5 average rating, 334 reviews

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.

Top guest favorite

A warm entryway is highlighted by a vintage wooden door with intricate detailing. A small dark table and a decorative vase are positioned nearby. Natural light filters through the sheer curtain, illuminating a framed mirror on the wall, creating a welcoming first impression.

Home in Beardstown

4.98 out of 5 average rating, 245 reviews

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.

Guest favorite

A set of vintage double doors features a soft blue-green hue and tall, arched glass panels, allowing light to filter through. The doors are mounted on a rustic sliding track, complementing the warm wooden flooring beneath.

Loft in Winchester

4.97 out of 5 average rating, 120 reviews

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!

Top guest favorite

A rustic log cabin, set on a grassy area, features a covered porch with rocking chairs. Sunlight filters through the surrounding trees, illuminating the wood exterior and stone steps. A small white cat is seen resting on the porch, adding a charming touch to the serene setting.

Place to stay in Virginia

4.99 out of 5 average rating, 322 reviews

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!

Top guest favorite

A well-equipped kitchen features modern appliances, including a stainless steel refrigerator and gas stove. A large island with a marble countertop provides seating for four. Light floods the space through overhead fixtures, enhancing the clean, organized layout that encourages home cooking.

Home in Quincy

4.99 out of 5 average rating, 168 reviews

❤️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.