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Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 Sept
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

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

1. Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (841 reviews)
"Pool was gorgeous! Breakfast was delicious!"
United States
Susan
The price is AU$118
includes taxes & fees
9 Sept - 10 Sept
Best Western Jacksonville Inn
A building entrance with a stone facade, a glass door, and two potted plants with flowers.

2. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (742 reviews)
"Friendly staff, clean room. The beds were comfortable."
United States
Dena
The price is AU$139
includes taxes & fees
14 Sept - 15 Sept
Sleep Inn & Suites South Jacksonville
A hotel lobby with seating areas, a television, and a reception desk.

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (539 reviews)
"The hotel is newly renovated and very clean!! Beds are super comfortable and the breakfast was excellent. They were still working on the fitness room while we were there, so we weren’t able to use that. But overall it was an excellent stay."
United States
Dawn
The price is AU$154
includes taxes & fees
20 Sept - 21 Sept
Hampton Inn Jacksonville
A modern dining area with a long table and chairs, a kitchen in the background, and a wall with colorful circular decorations.

4. 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, (495 reviews)
"Rooms were clean,just need some upgrading."
United States
Ellena
The price is AU$126
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Express Hotel & Suites Jacksonville by IHG
A hotel room with two beds, a wooden headboard, a bedside table with a phone, and a wall-mounted light fixture.

5. Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
8.0 out of 10, Very good, (45 reviews)
"The rooms are very clean and the staff is great ."
United States
Michael
The price is AU$97
includes taxes & fees
9 Sept - 10 Sept
Jacksonville Inn & Suites
A hotel room with two beds, a nightstand with a lamp, a phone, and a digital clock.

6. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (665 reviews)
"Clean room"
United States
Dave
The price is AU$93
includes taxes & fees
16 Sept - 17 Sept
Super 8 by Wyndham Jacksonville
A hotel lobby with a reception desk, seating area, and large windows.

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (504 reviews)
"Overall good place to stay"
United States
Mark
The price is AU$105
includes taxes & fees
8 Oct - 9 Oct
Quality Inn Jacksonville near I-72
A dining area with a wooden table and chairs, a patterned rug, and a kitchen in the background.

8. Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (26 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is AU$177
includes taxes & fees
15 Sept - 16 Sept
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
A hallway with a light blue wall, wooden shelves, and a door marked with the number 2.

9. Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (68 reviews)
"I travel for work and have stayed in a lot of different hotels / lodges I give this place 10 out of 10. Staff were welcoming, dad was extra comfortable, place was clean, quiet, great neighborhood in all of attractions were close by. This was by far the best stay yet. I highly recommend"
United States
Bruce
The price is AU$127
includes taxes & fees
13 Sept - 14 Sept
Monroe Street Suites
A cozy living area with a leather sofa, a wooden coffee table, and a patterned armchair. A brick wall and wooden shelves with various items are visible.

10. William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (370 reviews)
"Very cool historic hotel with a great location. Would definitely come back!!"
United States
Sam
The price is AU$127
includes taxes & fees
13 Sept - 14 Sept
William Watson Hotel
A row of brick houses with a well-maintained lawn and a large tree on the right.

11. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (173 reviews)
"Very clean , washer and dryer available ! "
United States
Stacy
The price is AU$118
includes taxes & fees
9 Sept - 10 Sept
Knights Inn Jacksonville East Morton Ave
A hallway with wooden doors leading to a dining area with a table and chairs.

12. Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (152 reviews)
"Enjoyed our stay at Green Acres! When we return we will definitely stay there again"
United States
Kimberly
The price is AU$179
includes taxes & fees
13 Sept - 14 Sept
Green Acres Hotel
A bakery display with various baked goods and packaged snacks.

13. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (142 reviews)
"We have stayed here a few times always very nice employees."
United States
Teresa
The price is AU$87
includes taxes & fees
4 Oct - 5 Oct
Rodeway Inn Pittsfield
A coffee maker on a counter, a framed picture of a boat on water, and a coffee bag on the wall.

14. Peace on the Prairie — Quiet Nature Retreat on 24 Acres

Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Murrayville
10.0 out of 10, Exceptional, (31 reviews)
"Exactly as described, wonderful experience."
United States
Petraborg P.
The price is AU$170
includes taxes & fees
14 Sept - 15 Sept
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
A rustic log cabin with a porch and a chimney.

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

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (17 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
The price is AU$222
includes taxes & fees
15 Sept - 16 Sept
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
A two-story building with a balcony on the upper floor, a front door, and a sign that reads "Peace on the Prairie Klein Prairie".

16. 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
Murrayville
9.8 out of 10, Exceptional, (69 reviews)
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
United States
Anonymous traveller
The price is AU$195
includes taxes & fees
11 Sept - 12 Sept
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
A wooden deck with a railing, surrounded by trees with autumn foliage.

17. 3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat
Chambersburg
10.0 out of 10, Exceptional, (2 reviews)
"If you like quiet, wildlife and beautiful trees, this is the perfect place. We loved our stay! Thanks to our host!"
United States
Carol
The price is AU$275
includes taxes & fees
13 Sept - 14 Sept
3-bedroom country home in Pike Co Il with AC and heat
A bedroom with a wooden headboard, a large bed with white bedding, a bench, and a dresser with a mirror.

18. The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (62 reviews)
"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "
United States
Gregory D.
The price is AU$231
includes taxes & fees
9 Sept - 10 Sept
The Farmhouse Loft "Greene County's Guesthouse"
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

8/10 Good
"Could be just a little cleaner and really could have used a handicap room"
Heather 2-night trip
Posted 1 day ago
Best Western Jacksonville Inn

Find out more about Winchester

Winchester B&B information

Number of reviews
1,715
Accommodation
1 B&B
Lowest Price
AU$87
Highest Price
AU$179

Frequently asked questions

Searching for B&Bs in Winchester?
If you're looking for a place to stay with fewer rooms than a hotel and an intimate environment, a bed and breakfast might be a great fit for your getaway to Winchester.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to meet guests from other places and of course a full breakfast to start the day, B&Bs provide a one-of-a-kind setting.
What are the best bed and breakfasts in Winchester?
Here is a B&B that guests like in the area: Blessings on State Bed & Breakfast: 2 rooms. 13.3 mi (21.4 km) from the heart of Winchester. Enjoy the designer toiletries and spa.
When is the best time to stay at a B&B in Winchester?
When you're dreaming of a getaway to Winchester, year-round temperatures and rainfall may be important factors to consider. 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.