Title: Book The Best Hotels in Winchester, IL for 2026 from CA $86 - Fully Refundable Options - Expedia.ca

 

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# Find hotels in Winchester, IL from CA $86

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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=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&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=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&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=2025-12-16&d1=2025-12-16&endDate=2025-12-18&d2=2025-12-18&amenities=PETS)

## Check prices for these dates

Tonight

[Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-12-02&endDate=2025-12-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 3 - Dec 4](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-12-03&endDate=2025-12-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 43 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![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)

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

![Lobby](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/3c66858b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Jacksonville

Jacksonville

8.2/10

Very good

(614)

"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 $77

CA $88 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Lobby](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/1b7c7a64.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

(617)

"Great stay!"

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

Alexis

CA $110

CA $122 total

includes taxes & fees

Dec 7 - Dec 8

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

![Indoor pool](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/df8698e3.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)

### Quality Inn Jacksonville near I-72

Jacksonville

7.8/10

Good

(425)

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

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

Angela

CA $77

CA $86 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

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

![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/513649eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Jacksonville Inn

Jacksonville

8.4/10

Very good

(742)

"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 3 - Dec 4

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

"Great stay"

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

Jeramy

CA $167

CA $183 total

includes taxes & fees

Dec 3 - Dec 4

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

![Front of property](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/b4ce7d70.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 $121

CA $133 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Breakfast meal](https://images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1.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)

![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/7000000/6660000/6659600/6659525/23a03799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### William Watson Hotel

Pittsfield

9.2/10

Wonderful

(345)

"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 $112

CA $124 total

includes taxes & fees

Dec 14 - Dec 15

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

![Reception](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/56f759a8.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)

![Reception](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/9192d41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Jacksonville

Jacksonville

8.8/10

Excellent

(496)

"Great property, great staff, comfy beds"

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

Mary Ann

CA $111

CA $126 total

includes taxes & fees

Dec 11 - Dec 12

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

(437)

"Overall decent, bathroom tiles were cracking, but other than that everything was good. "

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

Desi

CA $100

CA $111 total

includes taxes & fees

Dec 14 - Dec 15

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

![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/92a8744a.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)

![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

(852)

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

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

Charles

CA $95

CA $106 total

includes taxes & fees

Dec 3 - Dec 4

[](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)

![Exterior](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637460/e9aab2d4.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)

![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)

### Rodeway Inn

Pittsfield

6.8/10

(125)

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

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

David

CA $81

CA $89 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Pittsfield-Hotels-Rodeway-Inn.h5637460.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/fff007e8.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)

### 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)

![Exterior](https://images.trvl-media.com/lodging/10000000/9310000/9309500/9309491/e9218eec.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)

![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)

![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 $91

CA $104 total

includes taxes & fees

Dec 3 - Dec 4

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

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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 $110

CA $122 total

Dec 7 - Dec 8

includes taxes & fees

9.2/10 Wonderful! (615 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 3 - Dec 4

includes taxes & fees

8.4/10 Very Good! (740 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 $111

CA $126 total

Dec 11 - Dec 12

includes taxes & fees

8.8/10 Excellent! (492 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 $100

CA $111 total

Dec 14 - Dec 15

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 $77

CA $86 total

Jan 2 - Jan 3, 2026

includes taxes & fees

7.6/10 Good! (423 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 $77

CA $88 total

Jan 1 - Jan 2, 2026

includes taxes & fees

8.2/10 Very Good! (614 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

![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

"Friendly and inviting staff. Clean bathrooms and overall nice hotel. "

A verified traveller stayed at Sleep Inn & Suites South Jacksonville

Posted 7 days ago

[](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)

### Best Western Jacksonville Inn

5/5 Excellent

"Clean, quiet, easy, secure access, friendly front desk staff. Breakfast room clean and organized, staff friendly and helpful."

A verified traveller stayed at Best Western Jacksonville Inn

Posted 11 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 2 weeks 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 3 weeks ago

[](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.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 1 month 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 1 month 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 2 months 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 [Quality Inn Jacksonville near I-72](https://www.expedia.ca/Springfield-Hotels-Quality-Inn.h474237.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 35 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,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFNElEQVR4Xu3bQXLjOAxAUaa88HKO4KPoaNTRfBQdoZdepMIJQJCAFLk7mKqeRfz/JhZE8mmneDpT2v9QOQ7+RiCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJFZD3cug2Rm+t3cv1c/HnSPsl06U9yuf2TT7XPopVPxmkgByXgfSqnwxSQI7LQHrVT/6pSPUrPdHdpQ+3vj0itvGXPMpsfxYICAiIBKKBaCAzW6tdJ1L7zbtMbeFa7LWvo01+GKKj/UYJBAREfoCAFBAQ6/eIptvjqpmu0kBACogvAhmBSCAg5T8gax8surhX+/q7XZaLXIHcZLr2waKLe7Wvv9slCIiNQBZd3Kt9/d0uQUBs9DqIZ2tL+ad9yA91NVt1D49iyAwEpIFoINWvQHogIO2I7FOk9u3zxOejQ9VPBjkZHap+MsjJ6FD1k0FORoeqnwxyMjpU/WSQk9Gh6ieDnIwOVT85ICfp9rZ7x1/Ct+5H/zdnW/U8EJCTQA6BgJwEcujnIvaq1hNvsj1+xZZs1OQdb0W39UcpOxekgUgg/dMic5vWcSQIiAXSPy0yt2kdR/5cZO0nLv1qs+XyfVob1wGxO+tYpa/9Te5Uu9VAQDQQkAYCAjIKiL69LXvHa/raX2T7fO1ri2/dPZ3cu4R7INriW0FAQPqJIDLxjyDSqyL69m5yYmubrJXto7ldXe24Sh8FRAMBAQEBAfkWUsd2f8evfbD4ut2JYdzkW/dVfqgbAtFAQHogIDEQ7aURzZDSt7/LBz1Rt8uVbvdHmSfqX1xr8nT6wDMQEA0EpIGAgNjEP9oN/Q/VDznjJtO1I/pCD8jbdHWVubpxujMQEJB+G+QmU5AYCMi7LPMTZa236OLh+h9zyUg37gORxSD+EQQEZAYii0F2V2ux7XKnn2gv9HhiHaN9H5O4He6AgDQQC0QD8UBAdLutvc7pGl77ASny2n/M3wT27vb8HQ8CAmKBgGggIJquvcu+eaKmo7ndV9k2eZTxdPIDBKSBgFggICDfQUp4e1/69hZcX6XJKm2/yp9OAhmBgMRVILbdV2kgIHHVCyB248OQsHa8vc2VfKTJo+ioiHsMBAREAgEBARk9R+Zcv0+3MdJVNnqenWWBgICcBQLSQED22x/zHV/621tdq/b1d3nHyypLVzUZlfGbgAXSQEAsEBAQEJ34R0d0u7UW+4trQy7779NHxJ+ujjkICAgICAjI7xFbK3fGWnWtTc6QUZmrvjRXzUAKCMghkLnGtoOAfO1FkJPe585FLuWDvuOta3gUbf5y4CMJBOQkEBC5BAEB8ROtW5/rC32e2DryZifaUvtN4G6X8ighEBAQCQREAwFpR6T6lZ9o/9/SNdyLbR3RJuIjCcQD0UBAGogF4r00sn+hm6v/0fvR71zE1Xe8/Zuzrprpo2zySTZaICAgICAgtYH4yX9EStE/5lp0cVFE+rBD5UR1978J2NNZICAgICAgIElEW3Tx50jTVaev/dNAdAQCUkBAvgSiIxDPTpTt8URvCYvXMdJVujEEoiNvHSOQuD22hMXrGIHE7bElLF7HCCRujy1h8TpGIHF7bAmL1zECidtjS1i8jtE3kH03mcqXZ/+KPUdtfp/eZKn8cuDv+E1e+yGQBnIwQEBALJD28sjfCyQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpfg7yLzSYZKIBQDNDAAAAAElFTkSuQmCC)