Vacation rentals in Chapin

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Top-rated vacation rentals in Chapin

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Top guest favorite

The cabin's exterior is viewed from a grassy area, showcasing a covered porch with steps leading up to the entrance. Two white doors are framed by light-colored walls, while a red wreath adds a touch of color. The natural surroundings feature trees in the background.

Cabin in Winchester

4.96 out of 5 average rating, 173 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.

Guest favorite

The living room and kitchen area features a mix of warm pink walls and natural light. A dining table with chairs is adjacent to a kitchen counter. A sofa bed is present, complemented by decorative pillows. Soft lighting is provided by an ornate chandelier.

Guest suite in Pittsfield

4.82 out of 5 average rating, 136 reviews

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!!

Top guest favorite

The building features a classic architectural style with large bay windows and ornate detailing. The ground floor includes glass storefronts, while the upper level showcases decorative molding and an inviting façade in a warm maroon color.

Loft in Virginia

4.94 out of 5 average rating, 181 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

A bright kitchen area is highlighted by light wood cabinetry and a green patterned backsplash. Appliances include a white refrigerator and kitchen essentials situated on shelves. Two upholstered stools are positioned at the kitchen island, complementing the wood flooring and woven rug in the living space.

Loft in Pittsfield

4.92 out of 5 average rating, 76 reviews

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.

Top guest favorite

A two-story tiny house is positioned at the end of a grassy path, surrounded by native grasses and trees. A rainbow flag gently waves in the breeze, and several trees display autumn foliage, adding color to the serene landscape.

Townhouse in Murrayville

4.98 out of 5 average rating, 320 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

A cozy dining area is highlighted by a wooden table surrounded by four chairs. Antique stained glass windows illuminate the space with soft colors. A small kitchen area is visible in the background, featuring modern appliances and bright cabinetry.

Cabin in Jacksonville

4.97 out of 5 average rating, 357 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 small, modern building is presented with blue siding and a stone foundation. A wooden pathway leads to a white front door, bordered by simple landscaping with gravel. Lush greenery is visible on both sides, enhancing the sense of privacy.

Guesthouse in Carlinville

4.98 out of 5 average rating, 106 reviews

ThE HiDeAwAy

You’ll be surprised by what’s inside! We’ve designed this space to be more than just a place to stay — it’s an experience, because isn’t that what life’s all about? Perfectly located just two blocks from the town square and only steps from the iconic Million Dollar Courthouse, you’ll also be close to great restaurants and shops. Whether you’re visiting for family, business, or a well-deserved getaway, we hope your stay with us creates lasting memories.

Top guest favorite

A welcoming exterior of a bungalow is displayed, featuring light siding and a sloped roof. A decorative front porch is outlined by several steps and a railing. A large tree offers shade, while a flag enhances the inviting atmosphere. A fenced yard is visible in the background.

Home in Beardstown

4.98 out of 5 average rating, 267 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 cozy living area features a black sofa with decorative pillows and a wooden coffee table at its center. Natural light streams through two windows, illuminating the neutral tones and textured decor. A small accent chair and a patterned rug complete the inviting space.

Loft in Winchester

4.95 out of 5 average rating, 137 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!

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

4.98 out of 5 average rating, 349 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!

Guest favorite

The spacious bedroom features exposed brick walls and polished wooden flooring. A wooden bed with a decorative quilt is accompanied by an armchair and a small side table. Natural light enters through a window, enhancing the room's inviting ambiance. A wooden staircase leads to the upper level.

Guest suite in Petersburgh

4.93 out of 5 average rating, 102 reviews

Holly & Matt Suite @ Three Pines Petersburg

You are going to love the Holly and Matt suite. This unique, octagon-shaped, two story suite is set behind an 1875 Italianate mansion perched high atop one of Petersburg's many hills. There is a mini fridge, microwave, and coffee/tea station and serene views from your second story screened in porch. This suite is perfect for a 2 night visit up to an extended stay.

Top guest favorite

The exterior of the Little White House by the River is showcased with a wraparound porch featuring red rocking chairs. Lush green grass surrounds the house, while a decorative sign is positioned near a wooden fence, indicating the property's name.

Home in Beardstown

4.99 out of 5 average rating, 337 reviews

The Little White House by the River

Beardstown's original Airbnb location, our home is called the Little White House by the River, and offers a quiet place to stay that is literally a stone's throw (if you've got a decent arm) from the back waters of the Illinois and Sangamon Rivers. DUE TO MAJOR PLANNED RENOVATIONS, THIS LOCATION WILL NOT BE AVAILABLE AFTER SEPTEMBER 30. 2025.