Vacation rentals in Pleasant Hill

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Top-rated vacation rentals in Pleasant Hill

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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, 178 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

A spacious bedroom is visible through an open doorway, featuring a large bed framed by neutral-toned bedding and pillows. A wooden bench sits at the foot of the bed, while a minimalistic chair and small plant add a touch of decor. Natural light enters through a nearby window.

Cabin in Kampsville

4.96 out of 5 average rating, 47 reviews

Riverfront Cabin • Deck Views + 5 Acres

Welcome to The Riverhouse – a cozy cottage retreat perched on 5 private acres overlooking the Illinois River. Unwind on the wide back deck with sweeping views of the water, or enjoy a quiet morning coffee surrounded by nature. Inside, the home is thoughtfully styled with decor inspired by the river’s charm—think fishing, boating, and the laid-back rhythm of life on the water. Perfect for a weekend escape, a peaceful solo stay, or reconnecting with friends and family just steps from the river.

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, 137 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

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, 78 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 dining area is furnished with a wooden table surrounded by black chairs, complemented by framed artwork on the wall. The kitchen can be seen in the background, featuring wooden cabinetry and stainless steel appliances, providing a modern touch to the space.

Condo in Bowling Green

5 out of 5 average rating, 34 reviews

Cozy Townhouse Retreat

Welcome to "Cozy Townhouse Retreat," a beautifully designed new construction offering three cozy bedrooms and 2.5 baths. This modern home features high-speed internet, a convenient washer and dryer, and a cozy fire pit for those chilly evenings. Outside, enjoy an outdoor gas grill and seating area, ideal for entertaining or relaxing. With a one-car garage and off-street parking, convenience is at your doorstep. Experience comfort, style, and modern amenities all in one place!

Guest favorite

A serene bedroom features a spacious bed with soft, muted linens and decorative throw pillows. Natural light filters through the room, illuminating the rustic wooden accents and century-old hardwood floors. A decorative bench sits at the foot of the bed, enhancing the cozy atmosphere.

Apartment in Carrollton

4.88 out of 5 average rating, 163 reviews

Farmhouse Loft

Experience the life and hospitality of a quintessential small town - Carrollton, Illinois. A historic community located just off the beaten path, Carrollton convincingly captures the spirit of rural America. Inspired by the peaceful charm of country life, we showcase century-old hardwood floors, exposed brick walls and thoughtful design. Farmhouse Loft is a charming retreat on the historic courthouse square --enjoy life in a loft apartment overlooking the courthouse lawn!

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

4.98 out of 5 average rating, 365 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 single-story home with a welcoming covered porch is displayed. Greenery surrounds the house, and flower pots hang near the entrance. The porch features a pair of outdoor chairs, inviting relaxation. The light-colored exterior is complemented by a well-maintained lawn.

Home in Bowling Green

4.95 out of 5 average rating, 154 reviews

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.

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

4.94 out of 5 average rating, 140 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 two-story yellow brick home is set against a bright blue sky. White trim outlines the windows and porch, while a manicured lawn and landscaping decorate the front. The structure features multiple windows, providing ample natural light.

Home in Louisiana

4.93 out of 5 average rating, 43 reviews

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.

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, 355 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 modern kitchen is showcased with white cabinetry and stainless steel appliances. A marble island provides seating for four with metal stools. Natural light highlights the space, including a gas stove, oven, and built-in microwave, creating an inviting area for meal preparation.

Home in Quincy

4.93 out of 5 average rating, 330 reviews

❤️Quincy Quarters❤️

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.