Top 10 Hotels in Winchester, IL from ￥9,153 - Competitive Prices

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

Cozy little house in town with country view on backdeck. : This vacation home rental outside of Winchester offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books. See all vacation rentals in Winchester .

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Our top choices for Winchester hotels

A building entrance with a stone facade, a glass door, and two potted plants with flowers.

1. Sleep Inn & Suites South Jacksonville

Jacksonville

Suzanne

￥14,761 total

includes taxes & fees

Nov 22 - Nov 23

An indoor swimming pool with a wooden ceiling, brick walls, and a view of the outside.

2. Best Western Jacksonville Inn

Jacksonville

Craig

￥13,535 total

includes taxes & fees

Nov 8 - Nov 9

A covered outdoor area with columns, a bench, and a building entrance.

3. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

Thomas

￥13,708 total

includes taxes & fees

Nov 22 - Nov 23

A hotel lobby with seating areas, a television, and a reception desk.

4. Hampton Inn Jacksonville

Jacksonville

Dawn

￥15,345 total

includes taxes & fees

Nov 26 - Nov 27

A hotel room with two beds, a nightstand with a lamp, a phone, and a digital clock.

5. Super 8 by Wyndham Jacksonville

Jacksonville

Pawel

￥10,433 total

includes taxes & fees

Nov 22 - Nov 23

A hotel lobby with a reception desk, seating area, and large windows.

6. Quality Inn Jacksonville near I-72

Jacksonville

Michael

￥10,465 total

includes taxes & fees

Dec 4 - Dec 5

A hotel room with two beds, a wooden headboard, a bedside table with a phone, and a wall-mounted light fixture.

7. Jacksonville Inn & Suites

Jacksonville

Hilda

￥15,658 total

includes taxes & fees

Nov 8 - Nov 9

A cozy hotel lobby with a central bar area, a round table with chairs, a patterned rug, and a chandelier.

8. William Watson Hotel

Pittsfield

Caroline

￥13,618 total

includes taxes & fees

Nov 12 - Nov 13

A living room with a sofa, two wooden tables, a coffee table, a fireplace, and a large window with a view.

9. Knights Inn Jacksonville East Morton Ave

Jacksonville

Stacy

￥13,536 total

includes taxes & fees

Nov 8 - Nov 9

A hotel lobby with a wooden staircase, a ceiling fan, and a dining area in the background.

10. Green Acres Hotel

Pittsfield

Kimberly

￥20,517 total

includes taxes & fees

Dec 6 - Dec 7

11. Monroe Street Suites

Pittsfield

Isidro

￥19,245 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with two beds, a bedside table with a lamp, a window with curtains, and a mirror on the wall.

12. Rodeway Inn Pittsfield

Pittsfield

Stephanie

￥11,990 total

includes taxes & fees

Nov 30 - Dec 1

View all properties

Top Winchester Hotel Reviews

Sleep Inn & Suites South Jacksonville

Jacksonville

10/10 Excellent

Lucy

William Watson Hotel

Pittsfield

10/10 Excellent

Anonymous traveler

Hampton Inn Jacksonville

Jacksonville

10/10 Excellent

Kathleen

Best Western Jacksonville Inn

Jacksonville

10/10 Excellent

Allicent

Super 8 by Wyndham Jacksonville

Jacksonville

10/10 Excellent

This is an old motel that I chose for nostalgic reasons. I wish I hadn't. The smell of must was overpowering to the point I thought about changing motels. The room decor was interesting and unique. The desk chair was a mesh office chair—nice. Not located in a good part of town, but that part of town seems to be revitalizing. My review would be more positive if the must had cleared out with running the air for several hours.

Christian

Quality Inn Jacksonville near I-72

Jacksonville

10/10 Excellent

David

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

10/10 Excellent

Only issue we encountered was kind of a rude person working in the breakfast area. My husband likes his food hot and asked to use a microwave to heat his food up as it wasn't hot. And she said that could not be done and the food was hot when she put it out. I said something to the girl at the front desk and she was dumb founded as there is a microwave at her area that could of been used. Lady in breakfast area messed up as I always tip them usually very well. I will say the breakfast bar area is...

Brenda

Frequently Asked Questions

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

Cozy little house in town with country view on backdeck.: This vacation home rental outside of Winchester offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books. See all vacation rentals in Winchester.

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 to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For additional details about updating your trip to Winchester or cancelling it, go to https://www.expedia.com/service/.

What is the best accommodation for staying close to Abraham Lincoln Capital Airport (SPI)?

Howard Johnson Hotel & Suites by Wyndham Springfield is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.4 km) from Abraham Lincoln Capital Airport. Other choices near the airport include Wyndham Springfield City Centre and State House Inn – a Red Collection Hotel.

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 64 hotels and other accommodations in the surrounding area. Find out more about Winchester.

What is there to see in Winchester?

Places to visit in the wider area include Morgan County Fairgrounds, Future Champions Sport Complex, and Lake Jacksonville. You'll also find Governor Duncan Mansion and Jacksonville Community Park in the area. Check out what more to see and do in Expedia's Winchester guide.

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.

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

Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites South Jacksonville is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Best Western Jacksonville Inn and Jacksonville Inn & Suites. See all available top hotels, or vacation rentals in Winchester.

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Find hotels in Winchester, IL from ￥9,153

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Treat yourself

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Go beyond your typical stay in Winchester

Check prices for these dates

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Our top choices for Winchester hotels

1. Sleep Inn & Suites South Jacksonville

2. Best Western Jacksonville Inn

3. Holiday Inn Express Hotel & Suites Jacksonville by IHG

4. Hampton Inn Jacksonville

5. Super 8 by Wyndham Jacksonville

6. Quality Inn Jacksonville near I-72

7. Jacksonville Inn & Suites

8. William Watson Hotel

9. Knights Inn Jacksonville East Morton Ave

10. Green Acres Hotel

11. Monroe Street Suites

12. Rodeway Inn Pittsfield

Top Winchester Hotel Reviews

Sleep Inn & Suites South Jacksonville

10/10 Excellent

Frequently Asked Questions

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

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

Where can I learn more about changing or cancelling my trip to Winchester?

What is the best accommodation for staying close to Abraham Lincoln Capital Airport (SPI)?

What's it like to stay in Winchester?

What is there to see in Winchester?

What's the seasonal weather like in Winchester?

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

Explore a world of travel with Expedia