Vacation Homes in Jackson
Featured Vacation Homes in Jackson
On the Wine Trail - Minutes to Giant City, Shawnee Forest, SIU - Amazing Shower
Alto Pass IL
Stay at this vacation home in Alto Pass. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Peachbarn Winery and Von Jakob Winery & Brewery are located nearby.
Kitchen
Washer
* On the Wine Trail * Hot Tub * Wi-Fi *
Alto Pass IL
Stay at this vacation home in Alto Pass. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Peachbarn Winery and Von Jakob Winery & Brewery are located nearby.
Hot tub
Kitchen
Notting Hill Cottage
Alto Pass IL
Stay at this vacation home in Alto Pass. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Peachbarn Winery and Von Jakob Winery & Brewery are located nearby.
Hot tub
Kitchen
Sip, Hike, Relax - A Private 20-Acre Haven in Wine Country
Alto Pass IL
Stay at this vacation home in Alto Pass. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Peachbarn Winery and Von Jakob Winery & Brewery are located nearby.
Hot tub
Kitchen
Spacious 2 BR, 1 1/2 baths, hot tub, pool table, outside room, full kitchen
Anna IL
Book a stay at this family-friendly vacation home in Anna. Enjoy free WiFi, a pool table, and patios. Popular attractions Anna City Park and Lincoln Heritage Winery are located nearby.
Hot tub
Kitchen
Wine Trail, Cozy Cabin plus hot tub
Cobden IL
Stay at this vacation home in Cobden. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Owl Creek Vineyard and Rustle Hill Winery are located nearby.
Hot tub
Kitchen
Sunset Ridge - Cabin 4
Cobden IL
Stay at this vacation home in Cobden. Enjoy balconies, an in-room coffeemaker, and in-room fireplaces. Popular attractions Rustle Hill Winery and Owl Creek Vineyard are located nearby.
Hot tub
Kitchen
Quaint, Beautiful Home next to SEMO and Hospital
Cape Girardeau MO
Stay at this vacation home in Cape Girardeau. Enjoy laundry facilities, an in-room coffeemaker, and in-room fireplaces. Popular attractions Show Me Center and Isle Casino Cape Girardeau are located nearby.
Kitchen
Washer
Beautiful location in the secluded woods
Pomona IL
The price is CA $100 per night
CA $100
CA $209 total
Dec 8 - Dec 9
includes taxes & fees
Stay at this vacation home in Pomona. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Pomona Winery and Von Jakob Winery & Brewery are located nearby.
Kitchen
Washer
* Best Location on the Wine Trail! * Hiking Trail 1 min away * Wi-Fi *
Alto Pass IL
Stay at this vacation home in Alto Pass. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Peachbarn Winery and Von Jakob Winery & Brewery are located nearby.
Kitchen
Free WiFi
Room for the Whole Family to Enjoy Thanksgiving Together!
Carbondale IL
Stay at this vacation home in Carbondale. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hickory Ridge Public Golf Center and Railroaders Memorial are located nearby.
Kitchen
Washer
Magical Victorian near hiking / wine trail
Anna IL
The price is CA $290 per night
CA $290
CA $530 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this vacation home in Anna. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Anna City Park and Lincoln Heritage Winery are located nearby.
Kitchen
Washer
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.
Top trending hotels in Jackson
Drury Inn & Suites Jackson MO
225 Drury Lane Jackson MO
The price is CA $116 per night from Dec 8 to Dec 9
CA $116
CA $122 total
Dec 8 - Dec 9
includes taxes & fees
9.6/10 Exceptional! (1,011 reviews)
