Winchester Hotels

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Check prices for these dates

Tonight
9 Apr - 10 Apr
Tomorrow
10 Apr - 11 Apr
This weekend
10 Apr - 12 Apr
Next weekend
17 Apr - 19 Apr

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Our top choices for Winchester hotels

Restaurant

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (513 reviews)
"The staff was great. We were worried staying at a pet-friendly hotel, but the property and our room looked and smelled fresh and clean. My only complaint is that the beds were too firm for my taste. "
United States
Ellen
The price is €79
includes taxes & fees
30 Apr - 1 May
Hampton Inn Jacksonville
Desk, blackout curtains, iron/ironing board, free WiFi

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.0 out of 10, Good, (7 reviews)
"Room was great other than the mini fridge did not work. "
United States
Derek
The price is €58
includes taxes & fees
11 Apr - 12 Apr
Jacksonville Inn & Suites
Exterior

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (657 reviews)
"Staff was friendly, rooms were clean, breakfast was good."
United States
Brett
The price is €80
includes taxes & fees
7 May - 8 May
Sleep Inn & Suites South Jacksonville
Indoor pool

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (766 reviews)
"Inexpensive, clean friendly place to sleep."
United States
Rodney
The price is €73
includes taxes & fees
26 Apr - 27 Apr
Best Western Jacksonville Inn
Standard Room, 2 Queen Beds

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (628 reviews)
"Nice clean room, nice staff and the breakfast is great..."
United States
Mickey
The price is €54
includes taxes & fees
30 Apr - 1 May
Super 8 by Wyndham Jacksonville
Lobby

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (456 reviews)
"Room was easily accessible, pool was convenient and we both slept well in the comfy bed. "
United States
Donielle
The price is €68
includes taxes & fees
21 Apr - 22 Apr
Quality Inn Jacksonville near I-72
Breakfast meal

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (349 reviews)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is €80
includes taxes & fees
12 Apr - 13 Apr
William Watson Hotel
Free daily continental breakfast

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (143 reviews)
"Great stay"
United States
Jeramy
The price is €120
includes taxes & fees
13 Apr - 14 Apr
Green Acres Hotel
Hallway

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (61 reviews)
"A unique luxurious find for rest and respite on a long trip home. Would stay here again, without any hesitation!"
United States
Donna
The price is €92
includes taxes & fees
13 Apr - 14 Apr
Monroe Street Suites
Exterior

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, (454 reviews)
"Clean room and great breakfast."
United States
Maureen
The price is €88
includes taxes & fees
7 May - 8 May
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Exterior

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (166 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is €64
includes taxes & fees
13 Apr - 14 Apr
Knights Inn Jacksonville East Morton Ave
Free daily on-the-go breakfast

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (131 reviews)
"Great little hotel, perfect for an overnight pit stop "
United States
David
The price is €54
includes taxes & fees
10 May - 11 May
Rodeway Inn Pittsfield
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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Top Winchester Hotel Reviews

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
"This stop was well worth the drive off the main road! The host was very communicative before and during our stay, and had a plate of freshly baked cookies waiting for us upon arrival! We found everything clean, welcoming, pet-friendly and comfortable! The kids all thought the yard art was cool, our dogs were thankful for a spacious place to walk, and we enjoyed the peaceful and quiet sounds of nature. Two things to be mindful of for future travelers - if arriving after dark, the roads are a bit narrow and winding; stop for provisions in Jacksonville or other nearby town before going to the cabin. Both minor details but hopefully helpful tips for future guests! "
Tiffany V. 1-night trip
Posted 7 hours 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
The price is €54 per night from 26 Apr to 27 Apr
€54
26 Apr - 27 Apr
includes taxes & fees
8.2/10 Very Good! (627 reviews)

Frequently asked questions

Where is 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 traveller data. Two other options for your stay in the area are Best Western Jacksonville Inn and Quality Inn Jacksonville near I-72. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This holiday home rental outside of Winchester is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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 room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
How is it to stay in Winchester?
Those travelling to Winchester will definitely enjoy the sights to see and things to do. There are 36 hotels and other accommodation options 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 Old Orchard Country Club and Governor Duncan Mansion in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.

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