Hotels in Winchester

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Where to stay in Winchester?

Villa DeWolf
Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11 reviews)
  • cleanliness
    Historic 19th-century B&B near Jacksonville's cultural attractions and a train station.
The price is $275
$313 total
includes taxes & fees
Jan 22 - Jan 23
Villa DeWolf
Best Western Jacksonville Inn
Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (753 reviews)
The price is $70
$80 total
includes taxes & fees
Jan 22 - Jan 23
Best Western Jacksonville Inn
Monroe Street Suites
Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (58 reviews)
  • cleanliness
    Wake up to small-town charm with modern conveniences in central Illinois.
The price is $98
$108 total
includes taxes & fees
Jan 22 - Jan 23
Monroe Street Suites
William Watson Hotel
William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348 reviews)
  • cleanliness
    Experience local charm at a historic hotel in downtown Pittsfield with fitness center.
The price is $85
$93 total
includes taxes & fees
Jan 22 - Jan 23
William Watson Hotel
Knights Inn Jacksonville East Morton Ave
Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (165 reviews)
  • cleanliness
    Stay comfortably in Jacksonville with early breakfast and convenient parking options.
The price is $65
$74 total
includes taxes & fees
Jan 22 - Jan 23
Knights Inn Jacksonville East Morton Ave
Green Acres Hotel
Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141 reviews)
  • cleanliness
    Charming countryside escape in Pittsfield with easy access to local attractions.
The price is $89
$98 total
includes taxes & fees
Jan 22 - Jan 23
Green Acres Hotel
Rodeway Inn Pittsfield
Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (128 reviews)
  • cleanliness
    Cozy Pittsfield retreat near local attractions with complimentary amenities.
The price is $59
$65 total
includes taxes & fees
Jan 25 - Jan 26
Rodeway Inn Pittsfield
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, (447 reviews)
  • cleanliness
    Experience a serene getaway with excellent facilities by the Jacksonville Community Park.
The price is $83
$92 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hampton Inn Jacksonville
Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (502 reviews)
  • cleanliness
    Tranquil refuge near Jacksonville's cultural sites with convenient indoor pool.
The price is $81
$93 total
includes taxes & fees
Jan 29 - Jan 30
Hampton Inn Jacksonville
Sleep Inn & Suites South Jacksonville
Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (627 reviews)
  • cleanliness
    Enjoy the indoor pool and fitness center during your Jacksonville stay.
The price is $78
$86 total
includes taxes & fees
Feb 3 - Feb 4
Sleep Inn & Suites South Jacksonville
Super 8 by Wyndham Jacksonville
Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (619 reviews)
  • cleanliness
    Peaceful business motel offers free breakfast and Wi-Fi in quiet Jacksonville area.
The price is $57
$65 total
includes taxes & fees
Feb 8 - Feb 9
Super 8 by Wyndham Jacksonville
Quality Inn Jacksonville near I-72
Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (443 reviews)
  • cleanliness
    Take a dip in the indoor pool or explore Jacksonville, with attentive staff ready to assist.
The price is $59
$65 total
includes taxes & fees
Feb 20 - Feb 21
Quality Inn Jacksonville near I-72
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.

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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.