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, 163 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

An outdoor covered patio features string lights, creating a warm ambiance. A wooden table with benches and a grilling station are visible. Surrounding greenery and decorative planters add a natural touch, while comfortable seating arrangements invite relaxation.

Cabin in Camp Point

4.99 out of 5 average rating, 139 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

The entrance features a white door framed by red brick walls, complemented by a small welcome mat that reads 'Hello.' A green chair and a small black table are positioned nearby, along with a potted plant and a floral wreath on the door.

Apartment in Palmyra

4.98 out of 5 average rating, 99 reviews

Main Street Haven: King Suite

Welcome to our luxurious Main Street Haven, nestled in the heart of a picturesque small town only minutes away from Historic Hannibal (12min) and Quincy IL (18min). This charming ground level unit features a luxurious king size bed that will give you the restful sleep you deserve. The new bathroom is furnished with modern amenities, and the large living room provides ample space to relax and unwind. The full kitchen is perfect for preparing meals, and is equipped with everything you may need.

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, 138 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.

Guest favorite

A serene landscape featuring a solitary tree reflected in calm water. The setting sun casts gentle hues of pink and purple across the sky, while the moon is visible, adding to the tranquil ambiance of the Illinois River.

Home in Pittsfield

4.84 out of 5 average rating, 236 reviews

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!!! WE'RE HERE, IF YOU NEED YOUR PRIVATE TIME ALONE, AS WELL!!! ***NEW KEURIG; BRING YOUR K-CUPS!!!***

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

4.91 out of 5 average rating, 140 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, 164 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!

Top guest favorite

Townhouse in Murrayville

4.98 out of 5 average rating, 305 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, 339 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.

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, 122 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 serene lakeside view features a gentle slope of green grass leading to calm waters. A hammock hangs between two trees, offering a resting spot. A birdhouse and small structure are visible nearby, complemented by lush vegetation surrounding the area.

Place to stay in Virginia

4.99 out of 5 average rating, 326 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, 170 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.

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Other great vacation rentals in Pittsfield

Cabin in Pittsfield

5 out of 5 average rating, 4 reviews

Cozy Country Cabin Perfect for Families & Retreats

NicoleRating, 5 stars1 week ago

Great location for a friend reunion. Very peaceful location and less than 10min from town.

Top guest favorite

A laundry area is equipped with a washer and dryer, set against a backdrop of dark cabinetry. Above, neatly arranged towels are visible, contributing to a tidy appearance. The floor features a tiled design, enhancing the practicality of this space.

Home in Payson

4.96 out of 5 average rating, 54 reviews

15 minutes to Quincy! - 3 bedroom/2 Full Bath

ConorRating, 5 starstoday

Great place! Clean, well kept, all the amenities.

Top guest favorite

An outdoor porch features a large table surrounded by comfortable chairs, offering a view of the tranquil Illinois River. The area is shaded by an overhang, with a ceiling fan visible overhead, enhancing relaxation during warm days.

Home in Hardin

5 out of 5 average rating, 33 reviews

Riverfront Home in Calhoun County

DannyRating, 5 stars2 weeks ago

The River House was a great place to stay. Very relaxing and quiet. Restaurants were great and within walking distance. Thank you!

Guest favorite

A view from a window shows the historic Pike County Courthouse across the street, featuring a prominent clock tower. Soft white curtains partially frame the view, allowing natural light to brighten the interior while providing a glimpse of the green lawn in front of the building.

Loft in Pittsfield

4.91 out of 5 average rating, 70 reviews

Historic Loft on Adams

NicolasRating, 5 stars4 days ago

Great place to stay situated right next to the owner's restaurant. food was great as well. Included recommendations for local spots to go

Guest favorite

Home in Louisiana

4.92 out of 5 average rating, 38 reviews

The Yellow Rose Historic Home

DylanRating, 5 stars2 months ago

It is a wonderful old house. It has a bit of work to be done, but it is well worth the stay for the price point. If you have a bunch of people in town, you can get a great meal put together using the dishes and pans!

Guest favorite

Home in Pittsfield

4.83 out of 5 average rating, 12 reviews

Roots Lodge at Pittsfield Lake (Starlink Internet)

VinayRating, 5 stars2 weeks ago

Our stay at Ashli’s airbnb was excellent. The location was amazing. It welcomed us with calm and serene atmosphere. The Lodge was beautiful, well maintained and spacious for a large group of people. With that being said, the communication with the host was also smooth. We enjoyed our stay and would definitely recommend it.

Top guest favorite

A modern bathroom features a compact vanity with a sink and a mirror above, complemented by stylish light fixtures. Artwork is displayed on the wall, and a decorative box sits atop the toilet. Neutral tones and wooden accents create a clean, organized space.

Condo in Bowling Green

5 out of 5 average rating, 19 reviews

Cozy Townhouse Retreat

KathyRating, 5 stars1 week ago

The townhouse was comfortable and we loved the decor. The townhouse was easily assessable and we got in on the first try! We had our grandkids with us and they loved the bunk beds! Lots of cookware and dishes. Shelley was easy to reach. Would stay there again.

Top guest favorite

The exterior of a guest house is visible, featuring a covered porch with seating. A black and white color scheme is complemented by green landscaping and a fenced area. The roof is metal, with bright blue skies providing a clear backdrop.

Guesthouse in Hannibal

4.97 out of 5 average rating, 78 reviews

St. Christopher House

LisaRating, 5 stars4 days ago

This was a terrific place to stay and we enjoyed ourselves very much. The host thoughtfully left us a loaf of bread and some butter, and that meant we could just relax and eat toast for breakfast in the morning without having to rush around to find a place. Loved it. Definitely recommended.

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Vacation rentals in Pittsfield

Top-rated vacation rentals in Pittsfield

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