Hotels in Winchester
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Quality Inn Jacksonville near I-72
Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (432)
7.8/10
Good
(432)
- Take a dip in the indoor pool or explore Jacksonville, with attentive staff ready to assist.
The price is $59
$59
$65 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Rodeway Inn Pittsfield
Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (126)
6.8/10
(126)
- Cozy Pittsfield retreat near local attractions with complimentary amenities.
The price is $62
$62
$68 total
includes taxes & fees
Dec 28 - Dec 29
Super 8 by Wyndham Jacksonville
Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (617)
8.2/10
Very Good
(617)
- Peaceful business motel offers free breakfast and Wi-Fi in quiet Jacksonville area.
The price is $56
$56
$64 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Green Acres Hotel
Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
8.6/10
Excellent
(141)
- Charming countryside escape in Pittsfield with easy access to local attractions.
The price is $107
$107
$118 total
includes taxes & fees
Dec 25 - Dec 26
Sleep Inn & Suites South Jacksonville
Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (619)
9.4/10
Exceptional
(619)
- Enjoy the indoor pool and fitness center during your Jacksonville stay.
The price is $80
$80
$89 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn Jacksonville
Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (500)
8.8/10
Excellent
(500)
- Tranquil refuge near Jacksonville's cultural sites with convenient indoor pool.
The price is $81
$81
$93 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Best Western Jacksonville Inn
Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (746)
8.4/10
Very Good
(746)
The price is $75
$75
$85 total
includes taxes & fees
Dec 25 - Dec 26
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 star property
Jacksonville
7.8 out of 10, Good, (441)
7.8/10
Good
(441)
- Experience a serene getaway with excellent facilities by the Jacksonville Community Park.
The price is $80
$80
$89 total
includes taxes & fees
Jan 4 - Jan 5, 2026
William Watson Hotel
William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (347)
9.2/10
Wonderful
(347)
- Experience local charm at a historic hotel in downtown Pittsfield with fitness center.
The price is $85
$85
$93 total
includes taxes & fees
Dec 25 - Dec 26
Monroe Street Suites
Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
9.6/10
Exceptional
(57)
- Wake up to small-town charm with modern conveniences in central Illinois.
The price is $86
$86
$95 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Knights Inn Jacksonville East Morton Ave
Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (164)
6.8/10
(164)
- Stay comfortably in Jacksonville with early breakfast and convenient parking options.
The price is $65
$65
$74 total
includes taxes & fees
Dec 25 - Dec 26
Villa DeWolf
Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
10/10
Exceptional
(11)
- Historic 19th-century B&B near Jacksonville's cultural attractions and a train station.
The price is $275
$275
$313 total
includes taxes & fees
Dec 25 - Dec 26
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.
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.
Budget hotels in Winchester and vicinity
8.2 out of 10, Very Good, (617)
8.2/10
Very Good
(617)
The price is $56
$56
$64 total
includes taxes & fees
Jan 4 - Jan 5, 2026
7.8 out of 10, Good, (432)
7.8/10
Good
(432)
The price is $59
$59
$65 total
includes taxes & fees
Jan 2 - Jan 3, 2026
8.4 out of 10, Very Good, (746)
8.4/10
Very Good
(746)
The price is $75
$75
$85 total
includes taxes & fees
Dec 25 - Dec 26
Sleep Inn & Suites South Jacksonville
Sleep Inn & Suites South Jacksonville2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (619)
9.4/10
Exceptional
(619)
The price is $80
$80
$89 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Holiday Inn Express Hotel & Suites Jacksonville by IHG2.5 star property
Jacksonville
7.8 out of 10, Good, (441)
7.8/10
Good
(441)
The price is $80
$80
$89 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.8 out of 10, Excellent, (500)
8.8/10
Excellent
(500)
The price is $81
$81
$93 total
includes taxes & fees
Jan 1 - Jan 2, 2026
9.2 out of 10, Wonderful, (347)
9.2/10
Wonderful
(347)
The price is $85
$85
$93 total
includes taxes & fees
Dec 25 - Dec 26
9.6 out of 10, Exceptional, (57)
9.6/10
Exceptional
(57)
The price is $86
$86
$95 total
includes taxes & fees
Jan 1 - Jan 2, 2026
8.6 out of 10, Excellent, (141)
8.6/10
Excellent
(141)
The price is $107
$107
$118 total
includes taxes & fees
Dec 25 - Dec 26
10.0 out of 10, Exceptional, (11)
10/10
Exceptional
(11)
The price is $275
$275
$313 total
includes taxes & fees
Dec 25 - Dec 26
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.
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.
Go beyond your typical stay in Winchester
Pet friendly
Check out reviews of Winchester hotels guests love
Sleep Inn & Suites South Jacksonville
10/10 Excellent
"Courteous staff and clean rooms. Hard to beat. "
William Watson Hotel
10/10 Excellent
"Love this hotel! Very comfortable & clean. I was graciously upgraded to a suite for my stay and the room was amazing. This may not be the place for children but for a cozy, restful stay in a place with historic charm, it’s top notch and my absolute favorite stop."
Knights Inn Jacksonville East Morton Ave
2/10 Terrible
"Im waiting on my refund room was too dirty i didnt end up bookijg the manager said it was fine theyd refund my money yet its not in my account "
Best Western Jacksonville Inn
10/10 Excellent
"Very friendly people. A good place to stay. The pool looked great but we didn't have the opportunity to use it "
Quality Inn Jacksonville near I-72
10/10 Excellent
"Teresa at counter was very helpful. Room was spacious and clean. "
Hampton Inn Jacksonville
10/10 Excellent
"Amazing hotel. Nice amenities. Best breakfast set up I have seen in a long time. Great verity. Nice adds for the oatmeal, sliced almonds, cranberries and brown sugar. Dining area has a nice setup. "
Super 8 by Wyndham Jacksonville
10/10 Excellent
"We rec'd a refund for 2 nights when we had to leave 2 days early because of a family emergency. REALLY appreciated that!"
Holiday Inn Express Hotel & Suites Jacksonville by IHG
10/10 Excellent
"Didnt make it to breakfast but could still obtain banana and yoghurt. This was super nice of them. Had kecard glutch but Chris the evening desk man literally ran upstairs after rescanning ours to check that it worked. Beds were very comfy. Wood surfaces were a little worn...a minor flaw."
Baymont by Wyndham Jacksonville
10/10 Excellent
"Everything new and clean "
Frequently asked questions
Can I book a refundable hotel in Winchester?
If you need the flexibility to change your travel plans to Winchester, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winchester be like during my visit?
The warmest months in Winchester are usually July and August with an average temp of 73°F. January and February are the chilliest months when the average temp is 35°F. The rainiest months are May and April.
Why should I book my Winchester accommodation with Hotels.com?
There are plenty of reasons to book your Winchester travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.