Holiday houses in Pleasant Hill

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pleasant Hill

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse in High Hill

5 out of 5 average rating, 52 reviews

Farm Stay+Eclectic Vintage +Fresh Eggs+EV Charge

Our eclectic guesthouse is set on 80 acres of quiet magic, come unplug. Discover fun details in the art-filled interior, 1960s phone booth, and light-filled space boasting vintage finds and plants galore. Collect fresh eggs for breakfast, enjoy coffee on the expansive porch. Wander the flower and vegetable garden, hike the wooded trail, explore the creek & shower under the stars. Slow down, reconnect, recharge. 7mins off I-70, 30mins to Hermann & 50mins to both STL airport and Columbia.

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Guest favourite

The kitchen features white cabinetry and modern black appliances. A spacious countertop offers seating at two metal stools. Natural light filters through the windows, illuminating the wooden flooring and classic tile backsplash.

Home in Hannibal

4.95 out of 5 average rating, 221 reviews

Little House in the Hollow

Private Hot Tub • Pet-Friendly • Walk to Mark Twain Cave & Winery • Near Downtown Hannibal Relax in this PRIVATE cozy retreat perfect for families, couples, or business trips. Enjoy a private hot tub, fenced yard, fire pit, BBQ, fast Wi-Fi, full kitchen, and self check-in. Walk to the Caves, Winery, Trolley & MT Live Show; downtown is 2 miles away. Explore, unwind, and enjoy a comfortable stay close to Hannibal’s top attractions. Only Airbnb to offer a discount to the 4 ticketed attractions!

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Guest favourite

Cabin in Mozier

5 out of 5 average rating, 7 reviews

Nature Escape-170 Country Acres

Unwind at this one-of-a-kind cabin nestled on 170 private acres of rolling countryside. Perfect for families, couples, or small groups, this retreat blends rustic charm with modern comfort. Grill dinner on the deck, and gather around the firepit under a sky full of stars. Inside, you’ll find a cozy open layout with a fully equipped kitchen, inviting living spaces, and comfortable bedrooms with warm cabin décor. Large windows bring the outdoors in, offering views of the woods and water.

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Top Guest favourite

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, 408 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.

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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, 195 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.

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Guest favourite

A river cabin sits elevated on stilts, surrounded by lush greenery, with a spacious deck offering views of the Mississippi River. A concrete patio leads to the water's edge, where a wooden dock allows for easy access. The peaceful setting is enhanced by mature trees in the background.

Treehouse in Annada

4.9 out of 5 average rating, 89 reviews

“Exclusive” River Cabin on Stilts (3 bedroom)

Your Perfect Riverfront Getaway Awaits! Nestled in a laid-back river cabin community, this charming cabin offers stunning views of the mighty Mississippi River. Whether you're into fishing or simply soaking up nature, the abundant wildlife and serene setting make it the ideal place to unwind. This cabin, elevated on stilts to protect from seasonal flooding, features three spacious bedrooms, one bath, and recent updates. Don’t miss out – book your escape today!

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Guest favourite

A charming yellow exterior of the home is highlighted by a metal roof. A welcoming front porch features a bench and two chairs, surrounded by well-maintained greenery and a grassy area. Large windows allow natural light to fill the interior spaces.

Home in White Hall

4.92 out of 5 average rating, 106 reviews

The Humble Hideaway

Escape the hustle and bustle in our charming backyard oasis, just a short walk from Main Street. This private home offers a cozy patio, and all the comforts of home including a fire pit and dining table. The home itself is bright and airy with hardwood floors, and a new central air conditioning. Curl up on the plush sofa and enjoy the flat screen smart TV in the main living area or prepare a meal in the fully equipped kitchen with brand new appliances.

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Top Guest favourite

Condo in Bowling Green

5 out of 5 average rating, 66 reviews

Cozy Townhouse Retreat

Welcome to "Cozy Townhouse Retreat," a beautifully designed new construction multi level townhome offering 3 cozy bedrooms and 2.5 baths. This modern home features high-speed internet, convenient washer and dryer, and outdoor patio with 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

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Top 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, 386 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!

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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, 363 reviews

Pere Ridge Tree Escape with private hot tub

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.

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Guest favourite

A single-story blue home is displayed, featuring a spacious front yard and a well-maintained gravel driveway. A garage door is visible on the right side, while large windows allow natural light to enter the living space. The clear blue sky enhances the welcoming appearance of the home.

Home in Bowling Green

4.89 out of 5 average rating, 46 reviews

Cozy blue home

Welcome to our cozy blue home, in Bowling Green, Missouri. We are excited for your stay. We are located right in the middle of town that has fast access to all fast-food, sit-down eating, stores, parks, and gas stations around. We do allow dogs on our property, cats are not allowed, we apologize. Relax with the whole family at this peaceful place to stay.

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Top Guest favourite

A modern farmhouse is presented in a spacious landscape, featuring a sleek metal exterior and a black roof. A covered porch extends along the front, providing a shaded area. Lush green grass surrounds the building, and a tree-lined backdrop adds natural depth to the setting.

Home in Eolia

5 out of 5 average rating, 18 reviews

Dairy Farm Stay • Fresh Eggs & Milk • Peaceful 2BR

Escape to a quiet dairy farm where you can wake up to cows, calves, fresh eggs, and peaceful country views. Our cozy 2-bedroom farmhouse sleeps up to 7 and offers full kitchen, WiFi, and plenty of trailer parking. Perfect for families, hunters, workers, or anyone needing a quiet getaway Easy day trips to Bowling Green, Wentzville, or St. Louis

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