Title: Book the Best Jackson WINERY Hotels in 2025 | Expedia.ca [Hotels in Jackson](https://expedia.ca/Jackson-Hotels.d55765.Travel-Guide-Hotels)[Vacation Rentals in Jackson](https://expedia.ca/Jackson-Vacation-Rentals.d55765.Travel-Guide-VacationRentals)[Flights to Jackson](https://expedia.ca/Cheap-Flights-To-Jackson.d55765.Travel-Guide-Flights)[Jackson Car Rentals](https://expedia.ca/Car-Rentals-In-Jackson.d55765.Car-Rental-Guide)[Jackson Vacation Packages](https://expedia.ca/Jackson.d55765.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Jackson, MO from CA $127 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Jackson Winery Hotels Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=55765&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=55765&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=55765&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=55765&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Jackson Winery Hotels ![Property amenity](https://images.trvl-media.com/lodging/54000000/53350000/53348100/53348099/05fcda41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, 1 King Bed, Non Smoking (Mobility, Bathtub w/Grab Bars)](https://images.trvl-media.com/lodging/54000000/53350000/53348100/53348099/67f5d6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/54000000/53350000/53348100/53348099/47fa1edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/54000000/53350000/53348100/53348099/23518830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Jackson/Cape Girardeau Jackson 8.8/10 Excellent (630) "We had a restful stay very safe & clean! Friendly staff:)" CA $117 CA $127 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Jackson-Hotels-La-Quinta-Inn-Suites-By-Wyndham-JacksonCape-Girardeau.h53348099.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/32000000/31190000/31190000/31189922/d22aee4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31190000/31190000/31189922/4a0f272b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/32000000/31190000/31190000/31189922/ded6701c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31190000/31190000/31189922/6b2b149b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rest, Relax and Renew. Our log cabin experience awaits your arrival. Anna 10/10 Exceptional (396) "Clean comfortable cabin in a beautiful relaxing setting. Would definitely stay again." CA $163 CA $278 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Anna-Hotels-Rest.h31189922.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27150000/27145300/27145221/05ba3853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/28000000/27150000/27145300/27145221/867be2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27150000/27145300/27145221/95950b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/28000000/27150000/27145300/27145221/5d936793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary Glamping with Native American Appeal Anna 9.8/10 Exceptional (152) "My wife and I had a ball. We absolutely loved this cabin. " CA $209 CA $396 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Anna-Hotels-Contemporary-Glamping-With-Native-American-Appeal.h27145221.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103090000/103080200/103080140/193ecf29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103090000/103080200/103080140/e2d9442e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103090000/103080200/103080140/36b0a800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103090000/103080200/103080140/df1ce01d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful location in the secluded woods Pomona 10/10 Exceptional (52) "Our trip was to attend my son's graduation from SIU. The cabin was in an accessible spot to Carbondale and was great for the 5 of us. We enjoyed our stay!" CA $138 CA $250 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Pomona-Hotels-Beautiful-Location-In-The-Secluded-Woods.h103080140.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88869200/88869111/db83638f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/89000000/88870000/88869200/88869111/48434221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88870000/88869200/88869111/ddef3125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88870000/88869200/88869111/8845b0fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Minutes to Giant City - 6 Minutes to SIU - 4 Minutes to Shawnee Winetrail! Makanda 9.8/10 Exceptional (56) "Great value and plenty of room, with a nice deck and BBQ. Cabin 2 had separate rooms and a very spacious living room. I would stay there again and it is my favorite for the region." CA $278 CA $344 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Makanda-Hotels-3-Minutes-To-Giant-City-6-Minutes-To-SIU-4-Minutes-To-Shawnee-Winetrail.h88869111.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36690000/36688500/36688411/180-920b85ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/37000000/36690000/36688500/36688411/8efd6e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36690000/36688500/36688411/e295cf49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36690000/36688500/36688411/90-b5148e0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Cabin Retreat tamms 8.2/10 Very good (41) "This is a very nice, peaceful cabin. The host was very friendly and accommodating. I would definitely stay here again." CA $167 CA $282 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Tamms-Hotels-Beautiful-Cabin-Retreat.h36688411.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/52e075c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/f5ad31e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/d1990eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42540000/42533900/42533836/46dd8c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Weber Farm - Enjoy a beautiful 100 acre farm! Frohna 10/10 Exceptional (30) "Hosts were great. I just wish they had a second bath or atleast a larger bathroom. " CA $174 CA $276 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h42533836.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116290000/116288600/116288506/67134b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116290000/116288600/116288506/5b1e546f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116290000/116288600/116288506/39bdfc35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116290000/116288600/116288506/14363a53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Victorian near hiking / wine trail Anna 10/10 Exceptional (1) "This 1893 vintage property was impeccable. Perfection in its decor, comfort, amenities and hospitality. Every nook and cranny in this house provided unique surprises and entertaining features. We wished we had had the time to take advantage of the murder mystery package!! Maybe next time.Our host, Dana provided warmth and charm ensuring we had maximum enjoyment. Our group traveled to Southern Illinois primarily to experience the Cache River Reserve. This unique property exceeded all... CA $290 CA $549 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Anna-Hotels-Magical-Victorian-Near-Hiking-Wine-Trail.h116288506.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39680000/39671200/39671140/7bfe8087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39680000/39671200/39671140/09707f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/40000000/39680000/39671200/39671140/3f7db1ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/40000000/39680000/39671200/39671140/c221a56c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottage overlooking Lake Acre Dongola 10/10 Exceptional (99) "So Clean, Comfy and Serene!! Worth the drive for solitude." CA $220 CA $430 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Charming-Cabin-Overlooking-5-Acre-Lake.h39671140.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19260000/19252900/19252851/066095c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19260000/19252900/19252851/4af1938a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19260000/19252900/19252851/35a75be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/20000000/19260000/19252900/19252851/108eb25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loft Apartment Across From Semo University Houch Field House. Walk To Events Cape Girardeau 10/10 Exceptional (91) "This Vrbo was very clean and accurate to the listing. This was my second stay and it was amazing again the second time. " CA $209 CA $254 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Cape-Girardeau-Hotels-Loft-Apartment-Across-From-Semo-University-Houch-Field-House-Walk-To-Events.h19252851.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=2025-10-18&endDate=2025-10-19®ionId=55765&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Jackson Hotel Reviews ![Drury Inn & Suites Jackson MO](//images.trvl-media.com/lodging/1000000/50000/41100/41077/8996a36d_y.jpg) ### Drury Inn & Suites Jackson MO 10/10 Excellent "We just came in for one night to see our grandson play football. We come to Jackson often and always stay here. It is consistently excellent. Clean, friendly, staff is great. " [](https://expedia.ca/Sikeston-Hotels-Drury-Inn-Suites-Jackson-MO.h41077.Hotel-Information) ![Town House Inn](//images.trvl-media.com/lodging/12000000/11620000/11613500/11613476/5eb3395a_y.jpg) ### Town House Inn 10/10 Excellent "It was easy and quiet and an easy check in " [](https://expedia.ca/Sikeston-Hotels-Town-House-Inn.h11613476.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/860000/856000/855988/d2a0e781_y.jpg) ### Quality Inn 10/10 Excellent "nice stay" [](https://expedia.ca/Sikeston-Hotels-Quality-Inn.h855988.Hotel-Information) ![Comfort Suites Jackson-Cape Girardeau](//images.trvl-media.com/lodging/3000000/2560000/2555900/2555896/70460e25_y.jpg) ### Comfort Suites Jackson-Cape Girardeau 10/10 Excellent "Very nice and comfortable " [](https://expedia.ca/Sikeston-Hotels-Comfort-Suites-Jackson-Cape-Girardeau.h2555896.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - 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