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11 Nov - 12 Nov
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Top hotels and accommodation in Winchester

Breakfast meal
William Watson Hotel

William Watson Hotel

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (344)
"Small town feel, felt safe walking around at all times of the day. Was in town for a wedding and the location was perfect. AC worked great and beds were comfortable. "
United States
Melanie
The price is NZ$152
includes taxes & fees
5 Dec - 6 Dec
William Watson Hotel
Free daily on-the-go breakfast
Rodeway Inn

Rodeway Inn

2.0 star property
Pittsfield
6.8 out of 10, (122)
"Quick easy check-in, friendly staff"
United States
John
The price is NZ$121
includes taxes & fees
19 Nov - 20 Nov
Rodeway Inn
Desk, iron/ironing board, cots/infant beds, rollaway beds
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 star property
Jacksonville
7.0 out of 10, Good, (850)
"super comfy beds and pillow!"
United States
Patty
The price is NZ$134
includes taxes & fees
18 Nov - 19 Nov
Baymont by Wyndham Jacksonville
Indoor pool
Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 star property
Jacksonville
8.4 out of 10, Very good, (734)
"Nice staff"
United States
jacob
The price is NZ$151
includes taxes & fees
12 Nov - 13 Nov
Best Western Jacksonville Inn
Exterior
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (613)
"Great stay!"
United States
Alexis
The price is NZ$158
includes taxes & fees
16 Nov - 17 Nov
Sleep Inn & Suites South Jacksonville
Lobby
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2.0 star property
Jacksonville
8.2 out of 10, Very good, (611)
"Very nice staff, room was very clean, and the staff was very accommodating! I would stay here again"
United States
Jayla
The price is NZ$114
includes taxes & fees
11 Dec - 12 Dec
Super 8 by Wyndham Jacksonville
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, (434)
"It was clean with friendly staff"
United States
Christina
The price is NZ$155
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Restaurant
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 star property
Jacksonville
8.8 out of 10, Excellent, (490)
"Great spot "
United States
Chris
The price is NZ$160
includes taxes & fees
20 Nov - 21 Nov
Hampton Inn Jacksonville
Lobby sitting area
Green Acres Hotel

Green Acres Hotel

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Best room for the price. "
United States
Carol
The price is NZ$290
includes taxes & fees
12 Nov - 13 Nov
Green Acres Hotel
Lobby
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 star property
Jacksonville
7.8 out of 10, Good, (415)
"Easy check in and out very personable and friendly staff"
United States
Angela
The price is NZ$117
includes taxes & fees
12 Dec - 13 Dec
Quality Inn Jacksonville near I-72
Exterior
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

2.0 star property
Jacksonville
6.8 out of 10, (163)
"Great value. Nice, comfy bed, clean bedding, no-stink room. Did not expect to like this accommodation so much, but they surprised us!"
United States
Daniel
The price is NZ$129
includes taxes & fees
12 Nov - 13 Nov
Knights Inn Jacksonville East Morton Ave
Front of property
Villa DeWolf

Villa DeWolf

4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (10)
"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
Catherine
Villa DeWolf
Comfort Room
Monroe Street Suites

Monroe Street Suites

2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
"Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future."
United States
Jake
The price is NZ$229
includes taxes & fees
12 Nov - 13 Nov
Monroe Street Suites
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

Hampton Inn Jacksonville

Hampton Inn Jacksonville

10/10 Excellent
"Staff"
Ray 2-night trip
Posted 4 days ago
Hampton Inn Jacksonville

More cheap accommodation in Winchester

Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave, Jacksonville, IL
The price is NZ$151 per night from 12 Nov to 13 Nov
NZ$151
12 Nov - 13 Nov
includes taxes & fees
8.4/10 Very Good! (733 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 Super 8 by Wyndham Jacksonville. 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 35 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, Lake Jacksonville and Future Champions Sport Complex. You'll also find Jacksonville Community Park 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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