Title: Book The Best Hotels in Winchester, IL for 2025 from CA $90 - Fully Refundable Options - Expedia.ca

 

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# Find hotels in Winchester, IL from CA $90

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## Go beyond your typical stay in Winchester

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America&regionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&travelerType=family_friendly)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America&regionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=POOL)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Illinois%2C+United+States+of+America&regionId=3000435714&latLong=39.629769%2C-90.456235&adults=2&startDate=2025-12-05&d1=2025-12-05&endDate=2025-12-07&d2=2025-12-07&amenities=PETS)

## Check prices for these dates

Tonight

[Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 22 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-22&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 41 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, Ensuite (Double Queen Suite)](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8f50dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/8fabc5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/e9628a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### William Watson Hotel

Pittsfield

9.2/10

Wonderful

(344)

"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Druann

CA $115

CA $127 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information)

![Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/w3837h2569x3y3-79e6a5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/e975b6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/92a8744a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/b7e82af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Baymont by Wyndham Jacksonville

Jacksonville

7.0/10

Good

(851)

"Great location. Newly remodeled room. Friendly staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles

CA $96

CA $106 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Springfield-Hotels-Baymont-By-Wyndham-Jacksonville.h1304355.Hotel-Information)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/0aa674c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/13f55165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/16c3be32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/74c9995c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rodeway Inn

Pittsfield

6.8/10

(122)

"Great little hotel, perfect for an overnight pit stop "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David

CA $85

CA $94 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/fc256dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/1baf1987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/c30882b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Jacksonville Inn

Jacksonville

8.4/10

Very good

(737)

"Cleanest hotel I’ve stayed at"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher

CA $105

CA $120 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/5c8e6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/c41d8356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/2a692595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleep Inn & Suites South Jacksonville

Jacksonville

9.4/10

Exceptional

(613)

"Great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexis

CA $114

CA $126 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/w3840h2571x0y3-b5dd01e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/5476fe85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/69b3d11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Jacksonville

Jacksonville

8.2/10

Very good

(613)

"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

CA $79

CA $90 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/3b913bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/bb05caaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/29dda3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

7.8/10

Good

(436)

"It was clean with friendly staff"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christina

CA $111

CA $124 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/3cd6537f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/24c58aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/56f759a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Jacksonville

Jacksonville

8.8/10

Excellent

(491)

"Noe at the front desk was so friendly and the place was extremely clean and very quiet at night…"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul

CA $112

CA $127 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (New building)](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/2c579c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/c466d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/7da0a008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Green Acres Hotel

Pittsfield

8.6/10

Excellent

(141)

"Wonderful stay - was staying with a number of family members and it all worked out"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Richard

CA $167

CA $184 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Minibar, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/b85b01be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/22fcac0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/df8698e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Jacksonville near I-72

Jacksonville

7.8/10

Good

(421)

"Easy check in and out very personable and friendly staff"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Angela

CA $84

CA $93 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/e9218eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free toiletries, hair dryer](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/3b6ca79f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/70af4e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/b9129591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Knights Inn Jacksonville East Morton Ave

Jacksonville

6.8/10

(163)

"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott

CA $90

CA $102 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Springfield-Hotels-Knights-Inn-Jacksonville-East-Morton-Ave.h9309491.Hotel-Information)

![Comfort Room](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/7fa649ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/873e4e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/baf4a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/47811fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monroe Street Suites

Pittsfield

9.6/10

Exceptional

(57)

"We had a great stay and would recommend others to stay here!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brady

CA $165

CA $181 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/64356a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/14048be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/09335ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/fff007e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa DeWolf

Jacksonville

10/10

Exceptional

(11)

"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Catherine

[](https://www.expedia.ca/Jacksonville-Hotels-Villa-DeWolf.h76952694.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=2025-12-05&endDate=2025-12-06&regionId=3000435714&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## More cheap stays in Winchester

![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Sleep Inn & Suites South Jacksonville

2401 Holliday Ln Jacksonville IL

CA $114

CA $126 total

Dec 21 - Dec 22

includes taxes & fees

9.2/10 Wonderful! (613 reviews)

[](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information)

![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL

CA $105

CA $120 total

Dec 4 - Dec 5

includes taxes & fees

8.4/10 Very Good! (737 reviews)

[](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information)

![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL

CA $112

CA $127 total

Nov 30 - Dec 1

includes taxes & fees

8.8/10 Excellent! (491 reviews)

[](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information)

![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL

CA $111

CA $124 total

Dec 7 - Dec 8

includes taxes & fees

7.6/10 Good! (436 reviews)

[](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information)

![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL

CA $84

CA $93 total

Dec 20 - Dec 21

includes taxes & fees

7.6/10 Good! (421 reviews)

[](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information)

![Super 8 by Wyndham Jacksonville](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL

CA $79

CA $90 total

Nov 30 - Dec 1

includes taxes & fees

8.2/10 Very Good! (613 reviews)

[](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information)

## Hotels in Winchester with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

2 properties

[](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d3000435714.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

2 properties

[](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d3000435714.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

14 properties

[](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d3000435714.Travel-Guide-Filter-Hotels)

## Recent reviews of Winchester hotels

![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg)

### Best Western Jacksonville Inn

5/5 Excellent

"Cleanest hotel I’ve stayed at"

A verified traveller stayed at Best Western Jacksonville Inn

Posted 4 days ago

[](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information)

![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg)

### Quality Inn Jacksonville near I-72

5/5 Excellent

"Staff was very nice. Room was great. A few things in the room were outdated (fabric on chair needed mending) but that didn’t keep us from having a pleasant stay. Plenty of parking. "

A verified traveller stayed at Quality Inn Jacksonville near I-72

Posted 5 days ago

[](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information)

![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg)

### Hampton Inn Jacksonville

5/5 Excellent

"Noe at the front desk was so friendly and the place was extremely clean and very quiet at night…"

A verified traveller stayed at Hampton Inn Jacksonville

Posted 8 days ago

[](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information)

![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg)

### Sleep Inn & Suites South Jacksonville

5/5 Excellent

"Room was spotless, breakfast was great and place was quiet. One night stay, college visit"

A verified traveller stayed at Sleep Inn & Suites South Jacksonville

Posted 11 days ago

[](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information)

![Super 8 by Wyndham Jacksonville](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg)

### Super 8 by Wyndham Jacksonville

5/5 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!"

A verified traveller from HIGHLAND stayed at Super 8 by Wyndham Jacksonville

Posted 2 weeks ago

[](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information)

![William Watson Hotel](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg)

### William Watson Hotel

5/5 Excellent

"Everything about our stay was great. We will stay here again. The parking was good, as it was in front of the building. The restaurant was excellent."

A verified traveller stayed at William Watson Hotel

Posted 3 weeks ago

[](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information)

![Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c_y.jpg)

### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

5/5 Excellent

"We had such a great experience staying here. The property was beautiful and the hosts were very welcoming and friendly. The property was very pet friendly as well. We will definitely go back for the peace and quiet!"

A verified traveller stayed at Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

Posted 1 month ago

[](https://expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information)

![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg)

### Holiday Inn Express Hotel & Suites Jacksonville by IHG

5/5 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."

A verified traveller stayed at Holiday Inn Express Hotel & Suites Jacksonville by IHG

Posted 2 months ago

[](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information)

![PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!](https://images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/3f150da0_y.jpg)

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

5/5 Excellent

"Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. "

A verified traveller stayed at PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Posted 2 months ago

[](https://expedia.ca/Pittsfield-Hotels-PICKLEBALL.h34582445.Hotel-Information)

## Frequently asked questions

### What's the best place for a stay in Winchester?

> Located 12.3 mi (19.8 km) from the heart of Winchester, [Best Western Jacksonville Inn](https://www.expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) is a top choice for your stay based on our traveler data. Other good options for your trip to the area are [Sleep Inn & Suites South Jacksonville](https://www.expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) and [Hampton Inn Jacksonville](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information). See all available [top hotels](https://www.expedia.ca/Hotel-Search?regionId=3000435714), or [vacation rentals in Winchester](https://www.expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals).

### What's the top vacation rental that Winchester has to offer?

> [PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!](https://www.expedia.ca/Pittsfield-Hotels-PICKLEBALL.h34582445.Hotel-Information): This vacation home rental outside of Winchester is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all [vacation rentals in Winchester](https://www.expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals).

### If I need to cancel my hotel reservation in Winchester, will I receive a refund?

> Yes, the majority of hotel reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by [fully refundable](https://www.expedia.ca/Hotel-Search?regionId=3000435714&paymentType=FREE_CANCELLATION) to find flexible hotel deals in Winchester.

### What's it like to stay in Winchester?

> Those traveling to Winchester are sure to enjoy the sights to see and things to do. There are 33 hotels and other accommodations in the surrounding area. Find out more about [Winchester](https://www.expedia.ca/Winchester.dx3000435714).

### What is there to see in Winchester?

> Places to visit in the wider area include [Morgan County Fairgrounds](https://www.expedia.ca/Morgan-County-Fairgrounds-Jacksonville.d553248621560054950.Vacation-Attraction), [Lake Jacksonville](https://www.expedia.ca/Lake-Jacksonville-Jacksonville.d6124325.Vacation-Attraction), and [Future Champions Sport Complex](https://www.expedia.ca/Future-Champions-Sport-Complex-Jacksonville.d835797978406019072.Vacation-Attraction). You'll also find [Old Orchard Country Club](https://www.expedia.ca/Old-Orchard-Country-Club-Pittsfield.d553248621564478943.Vacation-Attraction) and [Governor Duncan Mansion](https://www.expedia.ca/Governor-Duncan-Mansion-Jacksonville.d835650687804203008.Vacation-Attraction) in the area. Check out what more to see and do in Expedia's [Winchester guide](https://www.expedia.ca/Winchester.dx3000435714).

### What's the seasonal weather like in Winchester?

> The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.

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-   [Book Hotels in Winchester on Expedia.com](https://www.expedia.com/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

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![QR code to download the app](data:image/png;base64,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)