Title: Book the Best Pleasant Hill WINERY Hotels in 2026 | Expedia.ca

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# Find Winery Hotels in Pleasant Hill, MO from CA $204

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## Check availability on Pleasant Hill Winery Hotels

Tonight

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=3000445417&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=3000445417&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000445417&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000445417&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Pleasant Hill hotels with winery

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95320000/95314200/95314125/ccf05a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95320000/95314200/95314125/863ca2fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/96000000/95320000/95314200/95314125/60bf9d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95320000/95314200/95314125/8ab2dad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly Renovated Stylish 3rd Floor Apartment 5 mins from Country Club Plaza

[](https://www.expedia.ca/Kansas-City-Hotels-Newly-Renovated-Stylish-3rd-Floor-Apartment-5-Mins-From-Country-Club-Plaza.h95314125.Hotel-Information)

Manheim Park

9.8/10

Exceptional

(55)

"Clean place. Will stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Keith D.

CA $96

CA $260 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Kansas-City-Hotels-Newly-Renovated-Stylish-3rd-Floor-Apartment-5-Mins-From-Country-Club-Plaza.h95314125.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1505000/1504922/8723cc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/2000000/1510000/1505000/1504922/0df758b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1505000/1504922/b580f14f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Courtyard](https://images.trvl-media.com/lodging/2000000/1510000/1505000/1504922/19294e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodstock Inn B&B

[](https://www.expedia.ca/Kansas-City-Hotels-Woodstock-Inn-BB.h1504922.Hotel-Information)

Independence

9.4/10

Exceptional

(318)

"Innkeeper was very friendly and the room was very clean and very well decorated."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jesseca

CA $169

CA $204 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Kansas-City-Hotels-Woodstock-Inn-BB.h1504922.Hotel-Information)

![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/49000000/49000000/48993600/48993516/28ceeae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/49000000/49000000/48993600/48993516/29405981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/49000000/49000000/48993600/48993516/04ec6130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, Balcony | Living area](https://images.trvl-media.com/lodging/49000000/49000000/48993600/48993516/e574f36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Meadowbrook

[](https://www.expedia.ca/Kansas-City-Hotels-The-Inn-At-Meadowbrook.h48993516.Hotel-Information)

Overland Park

9.8/10

Exceptional

(404)

"Absolutely wonderful stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Meredith

[](https://www.expedia.ca/Kansas-City-Hotels-The-Inn-At-Meadowbrook.h48993516.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87370000/87366800/87366751/382dba28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/88000000/87370000/87366800/87366751/d186bf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87370000/87366800/87366751/d3647eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87370000/87366800/87366751/w843h678x91y5-d59f47ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful-Clean-Modern-Convenient-Accessible Home 

[](https://www.expedia.ca/Overland-Park-Hotels-Beautiful-Clean-Modern-Convenient-Accessible-Home.h87366751.Hotel-Information)

Nall Hills

9.6/10

Exceptional

(59)

"house was perfect for us this weekend! very nice and in a great area, and the hosts were so kind. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Isabella M.

CA $242

CA $589 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Overland-Park-Hotels-Beautiful-Clean-Modern-Convenient-Accessible-Home.h87366751.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29&regionId=3000445417&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Pleasant Hill Hotel Reviews

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