Holiday rentals in Pleasant Hill

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Top-rated holiday rentals in Pleasant Hill

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Top guest favourite
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, 184 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 favourite
A cozy cabin is nestled among tall trees, featuring a welcoming front porch and a green door. The surrounding lawn is well-kept, with open fields visible in the distance, creating a peaceful and serene setting.
Guest house in Jerseyville
4.96 out of 5 average rating, 181 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 favourite
A porch swing with a plush cushion and decorative pillows is suspended from the ceiling. A small side table holds a drink and a vase with a fresh flower. Lush greenery surrounds the area, offering a peaceful outdoor setting.
Home in Bowling Green
4.96 out of 5 average rating, 214 reviews

Peaceful Country Cottage

Traveling for work or pleasure? Enjoy a peaceful country view while relaxing on the front porch. This home sits on 14 acres, just off US Highway 61. Guests will see deer roaming in the yard early morning and at night. This rental accommodates families traveling with children or the couple seeking a quiet retreat. Stay here while you visit family and friends in the area. It is a short drive to Vandalia, Louisiana, Hannibal or Mark Twain Lake. (40 Min). About one hour from St. Louis.

Top guest favourite
The interior of the cabin features exposed wooden beams and reclaimed logs, creating a rustic aesthetic. A comfortable sofa is positioned in front of a brick fireplace, which is flanked by a dresser. A small dining table and chairs occupy one corner, with a cozy area rug enhancing the warmth of the space.
Cabin in Jacksonville
4.97 out of 5 average rating, 755 reviews

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.

Guest favourite
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.
Flat in Carrollton
4.87 out of 5 average rating, 181 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 favourite
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
4.96 out of 5 average rating, 170 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.

Top guest favourite
The historic brick building, featuring a green roof, is surrounded by open grassy areas. Several flags are displayed in front, symbolizing heritage. Multiple sets of stairs lead to various entrances, highlighting the structure's two-story design and outdoor spaces for guests to enjoy.
Home in Pittsfield
4.85 out of 5 average rating, 251 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!!! PRIVATE TIME ALONE, Guaranteed!!! NEW KEURIG; BRING YOUR OWN K-CUPS!!!***

Top guest favourite
A cozy log cabin is set amidst tall trees, featuring a gabled roof and a stone foundation. The front porch is adorned with chairs and a charcoal grill, providing a shaded space. Surrounding greenery creates a tranquil, natural atmosphere.
Cabin in Brighton
4.97 out of 5 average rating, 102 reviews

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

Superhost
Flat in Pittsfield
5 out of 5 average rating, 4 reviews

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.

Guest favourite
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, 372 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 favourite
A modern studio cabin is elevated on pillars, surrounded by lush greenery. The exterior features dark wood siding and multiple windows, allowing natural light to illuminate the interior. A deck is visible, indicating outdoor space for relaxation.
Farm stay in Grafton
4.96 out of 5 average rating, 338 reviews

Pere Ridge Tree Escape

Welcome to Pere Ridge ! Enjoy the lovely setting of this romantic spot in nature. Pere Ridge is a custom Scandinavian inspired nature escape for two . Our elevated cabin is perched on a ridge with a deck that is surrounded by trees. Our hope is that you disconnect from life's stresses while at Pere Ridge. Our cabin is located in "the ridge " area of Grafton and is a 10 minute drive to Grafton.

Top guest favourite
A wooden dock extends over a calm lake, reflecting the surrounding trees and cloudy sky. A solitary chair is placed at the end of the dock, offering a peaceful spot to admire the serene waters.
Cottage in Montgomery City
4.99 out of 5 average rating, 397 reviews

Small private country home with lake, spa, firepit

Country setting, 3/4 mile from town, house on 20 acres, lake, woods in back round, firepit, spa and BBQ area under pergola. 10 minutes from I-70. 25 minutes to Warrenton, 30 minutes from Hermann, Mo. 50 minutes to Columbia and Wentzville, MO. Great place for a staycation, traveling, work from home, or a vacation. Child and pet friendly with lots of running room.

Popular amenities for Pleasant Hill holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Pike County
  5. Pleasant Hill