Winchester, IL

Travel Guide

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
$100 nightly
The price is $111 total per night from Oct 22 to Oct 23
$111 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sleep Inn & Suites South Jacksonville
Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave Jacksonville IL
$75 nightly
The price is $85 total per night from Sep 23 to Sep 24
$85 total
Sep 23 - Sep 24
Total with taxes and fees
Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (848 reviews)
"The carpet in our room was filthy and stained. The walls were peeling in the bathroom."

Reviewed on Sep 19, 2026

Best Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
$72 nightly
The price is $80 total per night from Sep 28 to Sep 29
$80 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prairie Land Heritage Museum and Jacksonville Community ...
8.2/10 Very Good! (54 reviews)
"Smells like an over whelming Indian food. Kids that live there running up and down the hallways. We didn’t stay there, we checked out and made other arrangements. I would give it 0 stars if possible."

Reviewed on Sep 20, 2026

Jacksonville Inn & Suites
See all 73 properties in Winchester
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.
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Bluffs IL
Stay at this vacation home in Bluffs. Enjoy laundry facilities, patios, and an in-room coffeemaker.
10/10 Exceptional! (64 reviews)
"Enjoyable stay, perfect for entertaining even in inclement weather. Hosts were friendly and welcoming, everything we could have needed was on site."

Reviewed on Aug 7, 2026

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat

Chambersburg IL
Enjoy free WiFi, laundry facilities, and in-room fireplaces.
9.6/10 Exceptional! (4 reviews)
"Property had all the amenities needed for a comfortable stay. Very private, quiet setting perfect for a relaxed stay."

Reviewed on Sep 11, 2026

3-bedroom country home in Pike Co Il with AC and heat
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Griggsville IL
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Old Orchard Country ...
10/10 Exceptional! (84 reviews)
"This is an expensive property and home, very well maintained, easily able to accommodate a large family group. The large inground pool with slide and a diving platform was fantastic. The young children in our group spent the majority of their time in the pool! The adults enjoyed the pool just as ..."

Reviewed on Aug 13, 2026

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
See all properties in Winchester
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.

Cities near Winchester

A historic building with a central portico, surrounded by modern residential buildings and a clear sky.

Jacksonville

A historic building with a prominent tower and an American flag.

Pittsfield

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