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Check prices for these dates

Tonight
Aug 7 - Aug 8
Tomorrow
Aug 8 - Aug 9
This weekend
Aug 7 - Aug 9
Next weekend
Aug 14 - Aug 16

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Our top choices for Winchester hotels

Restaurant
Reception
Reception
Fitness facility

1. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Nicole
￥12,800
￥14,590 total
includes taxes & fees
Aug 23 - Aug 24
Hampton Inn Jacksonville
Indoor pool
Lobby
Suite, 1 King Bed, Non Smoking, Jetted Tub | Soundproofing, iron/ironing board, cribs (free), high-speed internet
Reception

2. Best Western Jacksonville Inn

Best Western Jacksonville Inn
Jacksonville
United States
Ken
￥12,612
￥14,375 total
includes taxes & fees
Aug 9 - Aug 10
Best Western Jacksonville Inn
Exterior
Lobby
Lobby
Desk, iron/ironing board, WiFi (free), bed sheets

3. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Diane
￥14,563
￥16,162 total
includes taxes & fees
Sep 6 - Sep 7
Sleep Inn & Suites South Jacksonville
Standard Room, 2 Queen Beds | Desk, iron/ironing board, cribs (free), WiFi
Free daily continental breakfast
Lobby
Desk, iron/ironing board, cribs (free), WiFi

4. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
William
￥9,698
￥11,053 total
includes taxes & fees
Aug 23 - Aug 24
Super 8 by Wyndham Jacksonville
Desk, blackout drapes, iron/ironing board (on request), WiFi (free)
Exterior
Deluxe Single Room, 1 King Bed, Non Smoking | Living area
Combined shower/tub, hair dryer, towels, soap

5. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Kenneth
￥10,329
￥11,464 total
includes taxes & fees
Sep 7 - Sep 8
Jacksonville Inn & Suites
Lobby
Indoor pool
Free daily self-serve breakfast
Minibar, desk, soundproofing, iron/ironing board

6. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Mark
￥10,776
￥11,959 total
includes taxes & fees
Sep 6 - Sep 7
Quality Inn Jacksonville near I-72
Exterior
Exterior
Exterior
Free daily buffet breakfast

7. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Maureen
￥13,311
￥14,773 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Breakfast meal
Breakfast meal
Lobby
Lobby

8. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Beth
￥13,402
￥14,739 total
includes taxes & fees
Aug 8 - Aug 9
William Watson Hotel
Exterior
Lobby
Property amenity
Desk, cribs (free)

9. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
￥11,825
￥13,478 total
includes taxes & fees
Aug 9 - Aug 10
Knights Inn Jacksonville East Morton Ave
Free daily on-the-go breakfast
Standard Double Room, 2 Double Beds, Non Smoking | Bathroom | Free toiletries, hair dryer, towels
Exterior
Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, WiFi (free), alarm clocks

10. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Thor
￥8,845
￥9,728 total
includes taxes & fees
Aug 30 - Aug 31
Rodeway Inn Pittsfield
Hallway
Front of property
Lobby sitting area
Comfort Room | Premium bedding, desk, blackout drapes, soundproofing

11. Monroe Street Suites

Monroe Street Suites
Pittsfield
United States
Donna
￥15,412
￥16,951 total
includes taxes & fees
Aug 12 - Aug 13
Monroe Street Suites
Free daily continental breakfast
Coffee service
Interior
Standard Room, 1 King Bed, Accessible | Desk, WiFi (free), bed sheets

12. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Riley
￥18,575
￥20,429 total
includes taxes & fees
Aug 10 - Aug 11
Green Acres Hotel
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Top Winchester Hotel Reviews

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

10/10 Excellent
"The place is excellent for the price. Clean and modern. Will definitely stay there again."
Ken 1-night trip
Posted 13 hours ago
Sleep Inn & Suites South Jacksonville
Best Western Jacksonville Inn

Best Western Jacksonville Inn

8/10 Good
"No road noise, but the air conditioners and dehumidifiers ran all night. We went to breakfast late. The gravy (biscuits & gravy) was great because it was gone. "
Dennis 1-night trip
Posted 15 hours ago
Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

10/10 Excellent
"Conveniently located"
Julie 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10/10 Excellent
"Beautiful serene setting and cozy cabin, great hosts!"
Lauren L. 1-night trip
Posted 2 days ago
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
William Watson Hotel

William Watson Hotel

10/10 Excellent
"Perfect location to travel everywhere I needed."
Holly 1-night trip
Posted 3 days ago
William Watson Hotel
Hampton Inn Jacksonville

Hampton Inn Jacksonville

10/10 Excellent
"Fabulous!"
Nicole 1-night trip
Posted 5 days ago
Hampton Inn Jacksonville
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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

10/10 Excellent
"David met us at the property and he was early. He showed us around and demonstrated how to use pool equipment. He also stopped by mid morning the next day to see if we had any questions. Both hosts communicated quickly when we had questions. This is one of the best properties our family has ever rented. A great place with stuff to do in all kinds of weather and for all ages. The pool and nice kitchen/dining setup were highlights."
Robert H. 3-night trip
Posted 8 days ago
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

8/10 Good
"My reserved check in was easy. The attendant was polite, knowledgeable and informative. Will surely recommend. Sjr"
Sam 1-night trip
Posted 10 days ago
Super 8 by Wyndham Jacksonville
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

10/10 Excellent
"An outstanding place and excellent host. The prairie setting is absolutely sublime, and the house was clean and cozy. It had everything we needed, including fresh cookies! We wish we would have stayed longer. Kevin was very responsive to our messages and even gave us a tour of his incredible prairie and grounds. You won’t find another place like this: it’s a complete original. Looking for an excuse to come back again for a longer stay."
Mark 1-night trip
Posted 2 weeks ago
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
￥9,698
￥11,053 total
Aug 23 - Aug 24
includes taxes & fees
8.2/10 Very Good! (658 reviews)
Super 8 by Wyndham Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
￥10,329
￥11,464 total
Sep 7 - Sep 8
includes taxes & fees
Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
￥10,776
￥11,959 total
Sep 6 - Sep 7
includes taxes & fees
Quality Inn Jacksonville near I-72
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
￥12,612
￥14,375 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very Good! (827 reviews)
Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
￥12,800
￥14,590 total
Aug 23 - Aug 24
includes taxes & fees
8.8/10 Excellent! (532 reviews)
Hampton Inn Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL
￥13,311
￥14,773 total
Sep 6 - Sep 7
includes taxes & fees
7.8/10 Good! (486 reviews)
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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 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 and Super 8 by Wyndham Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental that Winchester has to offer?
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!: This vacation home rental outside of Winchester offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. 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 65 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 Governor Duncan Mansion. You'll also find Lake Jacksonville and Old Orchard Country Club 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.

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