Search B&B in Winchester

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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare B&B in Winchester with updated reviews, rates, and availability.

Sleep Inn & Suites
Exterior

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (473)
"Nice, clean place. No funny odors or mold. Seems fairly new. Reasonably priced. I’d stay again."
The price is SAR 318
SAR 353 total
includes taxes & fees
24 Feb - 25 Feb
Sleep Inn & Suites
Best Western Jacksonville Inn
Indoor pool

Best Western Jacksonville Inn

2.5 star property
8.4 out of 10, Very Good, (632)
"Stayed overnight for a business trip. Very friendly staff. Prompt service at check in. The room was very good."
The price is SAR 281
SAR 321 total
includes taxes & fees
13 Feb - 14 Feb
Best Western Jacksonville Inn
Quality Inn Jacksonville near I-72
Pool

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (355)
"Nice & clean, excellent amenities in the room. Very comfortable."
The price is SAR 237
SAR 264 total
includes taxes & fees
13 Mar - 14 Mar
Quality Inn Jacksonville near I-72
Super 8 by Wyndham Jacksonville
Exterior

Super 8 by Wyndham Jacksonville

2.0 star property
8.2 out of 10, Very Good, (561)
"Clean, comfortable and friendly staff! I will definitely stay here again! "
The price is SAR 210
SAR 240 total
includes taxes & fees
13 Mar - 14 Mar
Super 8 by Wyndham Jacksonville
Hampton Inn Jacksonville
Exterior

Hampton Inn Jacksonville

2.5 star property
8.8 out of 10, Excellent, (427)
"They did a good job. The only thing I didn’t like is they don’t have housekeeping everyday so you had to go ask for towels and things "
The price is SAR 316
SAR 360 total
includes taxes & fees
23 Feb - 24 Feb
Hampton Inn Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Exterior

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
7.8 out of 10, Good, (376)
"It smelled clean n easy parking"
The price is SAR 259
SAR 287 total
includes taxes & fees
16 Feb - 17 Feb
Holiday Inn Express Hotel & Suites Jacksonville by IHG
River's Edge Motel
Interior

River's Edge Motel

2.0 star property
8.8 out of 10, Excellent, (312)
"It's an older property, but it's very well cared for and very clean."
The price is SAR 281
SAR 319 total
includes taxes & fees
13 Feb - 14 Feb
River's Edge Motel
Baymont by Wyndham Jacksonville
Exterior

Baymont by Wyndham Jacksonville

2.5 star property
7.0 out of 10, Good, (773)
"The hotel was very basic, but clean and inexpensive. As other reviews have said, the hotel was under renovation. The breakfast was really lacking, but again, for the low price, I was not expecting much."
The price is SAR 223
SAR 248 total
includes taxes & fees
9 Mar - 10 Mar
Baymont by Wyndham Jacksonville
Americas Best Value Inn Beardstown
Exterior

Americas Best Value Inn Beardstown

2.0 star property
5.2 out of 10, (166)
"Good place "
The price is SAR 306
SAR 333 total
includes taxes & fees
13 Feb - 14 Feb
Americas Best Value Inn Beardstown
Super 8 by Wyndham Jerseyville
Exterior

Super 8 by Wyndham Jerseyville

2.0 star property
8.0 out of 10, Very Good, (287)
"Only drawback was my next door neighbor was up at 4:00am watching tv loud. Other than that was a great stay. Hotel staff do a great job. I was traveling alone & felt safe the whole time "
The price is SAR 328
SAR 364 total
includes taxes & fees
18 Feb - 19 Feb
Super 8 by Wyndham Jerseyville
William Watson Hotel
Lobby

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (316)
"Nice stay"
The price is SAR 334
SAR 367 total
includes taxes & fees
22 Feb - 23 Feb
William Watson Hotel
Come see what our Historical town has to offer!
Room

Come see what our Historical town has to offer!

4.8 out of 10, (3)
"I didn't get to stay at the property. The owner never gave me access. Never communicated at all via VRBO, email, text, or phone. I called the owner and owner was not receiving voicemail. I called VRBO. I have a case number to try to get a refund. I had to stay at a hotel. I never received the access code or communication. Very disappointed. Waiting a refund. Hoping I am not ripped off."
Come see what our Historical town has to offer!
Villa DeWolf
Front of property

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (6)
"What a truly beautiful place for a quick getaway. The owner went out of his way to ensure that we felt at home and welcomed. In addition to the ambiance of setting, the owner prepared a delicious breakfast of blueberry pancakes, bacon and fruit. We couldn’t ask for a better stay and we will make sure that we stay again during our next trip to Chicago ❤️"
The price is SAR 1,031
SAR 1,175 total
includes taxes & fees
13 Feb - 14 Feb
Villa DeWolf
Rodeway Inn
Room

Rodeway Inn

2.0 star property
6.8 out of 10, (113)
"This motel is more than 70 years old. The owners have made significant upgrades to a very old motel. Room looks nice upon entry and it was impeccably clean. The bed was possibly the best i have encountered in years. What you cant change are 2 foot by 2 foot showers, and a lack of heating controls during the cold months. It's an old central baseboard heating system for the whole operation. Staff was helpful and pleasant. This motel is a good budget option, but its still very old."
The price is SAR 243
SAR 267 total
includes taxes & fees
15 Mar - 16 Mar
Rodeway Inn
Green Acres Hotel
Front of property

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (122)
" very clean , friendly staff , convenient to restaurants ."
The price is SAR 446
SAR 491 total
includes taxes & fees
21 Feb - 22 Feb
Green Acres Hotel
Blessings on State Bed & Breakfast
Front of property

Blessings on State Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (55)
"Excellent property with welcoming staff and cozy, well-appointed rooms. "
The price is SAR 971
SAR 1,107 total
includes taxes & fees
18 Feb - 19 Feb
Blessings on State Bed & Breakfast
Knights Inn Jacksonville East Morton Ave
Exterior

Knights Inn Jacksonville East Morton Ave

2.0 star property
6.8 out of 10, (159)
"Not good shower head broke. Bath tub won’t plug closed so I had to use a new rag as a plug. Toilet barely flushed. Tv wouldn’t switch off pc mode and air conditioning won’t even do fan mode. Kept beeping clean filter and not staying on "
The price is SAR 244
SAR 278 total
includes taxes & fees
13 Feb - 14 Feb
Knights Inn Jacksonville East Morton Ave
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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Other property types in Winchester

Idyllic Mt Sterling Retreat w/ Private Lake!
Mt Sterling Vacation Rental | 4BR | 3.5BA | Stairs Required | 4,200 Sq Ft

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (5)
"My brother and our families (4 adults, 5 teens) stayed at the Hideaway along with our 2 dogs. Great place! Plenty of comfortable beds for all to have their own space. Living room area and the large dining table was great for playing board games. The dogs (and kids) loved running around in the woods and around the lake. The kitchen is massive, with plenty of room for multiple people to cook and well stocked with every type of pan, utensil or sharp knife you might need! We definitely will...
Idyllic Mt Sterling Retreat w/ Private Lake!
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Summertime

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (50)
"We stayed a few nights. House is clean and in very good shape. People are very nice and easy to work with."
The price is SAR 731
SAR 821 total
includes taxes & fees
13 Feb - 14 Feb
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
The Farmhouse Loft "Greene County's Guesthouse"
Room

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (53)
"We had an overnight stay during a very long roadtrip, the loft was perfect and we were able to have a very relaxing night after eating some of the best pizza I have ever had, highly recommend the place just a few hundred feet away. Communication with owners was perfect."
The price is SAR 319
SAR 581 total
includes taxes & fees
23 Feb - 24 Feb
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.

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find an accommodation with fewer rooms than a hotel and an intimate environment, a bed and breakfast might be just the right fit for your vacation to Winchester.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to interact with the owner, and tasty breakfasts, B&Bs offer a unique setting.
What are the best bed and breakfasts in Winchester?
Here are some B&Bs in the area: Villa DeWolf: 4 rooms. 13.5 mi (21.8 km) from the heart of Winchester. Enjoy the free cooked breakfast and designer toiletries. Blessings on State Bed & Breakfast: 2 rooms. 13.3 mi (21.4 km) from the downtown core. Enjoy the designer toiletries and spa.
When should I stay at a B&B in Winchester?
When you’re dreaming of a trip to Winchester, year-round temperatures and rainfall may be important factors to consider. 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 is there to do in Winchester?
If you want to check out some popular attractions in Winchester, you might enjoy a visit to Jacksonville Community Park. Morgan County Fairgrounds and Lake Jacksonville are also some sites to visit if you want to see more of the area.