Find a Bed and Breakfast in Winchester from CA $87

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Check prices for these dates

Next weekend
May 15 - May 17
In two weeks
May 22 - May 24
In one month
Jun 5 - Jun 7
In two months
Jul 3 - Jul 5
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Desk, blackout drapes, iron/ironing board, free WiFi

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.8 out of 10, Good, (13 reviews)
"Room was great other than the mini fridge did not work. "
United States
Derek
The price is CA $86
CA $95 total
includes taxes & fees
May 20 - May 21
Jacksonville Inn & Suites
Restaurant

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (517 reviews)
"I enjoyed the staff very professional"
United States
Gill
The price is CA $135
CA $154 total
includes taxes & fees
May 9 - May 10
Hampton Inn Jacksonville
Indoor pool

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (782 reviews)
"Clean room. Nice pool and a good breakfast"
United States
Thomas
The price is CA $102
CA $117 total
includes taxes & fees
May 10 - May 11
Best Western Jacksonville Inn
Exterior

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (672 reviews)
"Good breakfast stayed here several times in last couple monthd. Great staff "
United States
Keith
The price is CA $113
CA $125 total
includes taxes & fees
May 21 - May 22
Sleep Inn & Suites South Jacksonville
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, (634 reviews)
"Rooms where clean wifi was easy to connect to"
United States
Arron
The price is CA $78
CA $89 total
includes taxes & fees
May 21 - May 22
Super 8 by Wyndham Jacksonville
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 CA $133
CA $147 total
includes taxes & fees
May 10 - May 11
Monroe Street Suites
Breakfast meal

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (355 reviews)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is CA $107
CA $117 total
includes taxes & fees
May 12 - May 13
William Watson Hotel
Exterior

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, (65 reviews)
"Kevin was an excellent host and the house on the prairie was exactly what we needed after a long day of travel. We were surprised with fresh baked cookies upon arrival.The house was very cozy and walking the trails of the prairie was great for our pup. We would definitely stay here again the future!"
United States
David S.
The price is CA $151
CA $189 total
includes taxes & fees
May 13 - May 14
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
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, (459 reviews)
"The rooms were clean and the place smelt great. The staff was great. A lot of things had evidence of chronic war. The TV in our room was broken. For the price I expected a little bit more, but I did love the Staff."
United States
Andrew
The price is CA $135
CA $150 total
includes taxes & fees
May 24 - May 25
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Lobby

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (459 reviews)
"Room was easily accessible, pool was convenient and we both slept well in the comfy bed. "
United States
Donielle
The price is CA $92
CA $102 total
includes taxes & fees
May 14 - May 15
Quality Inn Jacksonville near I-72
Free daily continental breakfast

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (145 reviews)
"Good place to stay!"
United States
Riley
The price is CA $144
CA $158 total
includes taxes & fees
May 10 - May 11
Green Acres Hotel
Exterior

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, (12 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is CA $176
CA $215 total
includes taxes & fees
May 25 - May 26
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Free daily on-the-go breakfast

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (132 reviews)
"Great little hotel, perfect for an overnight pit stop "
United States
David
The price is CA $79
CA $87 total
includes taxes & fees
May 24 - May 25
Rodeway Inn Pittsfield
2 bedrooms, desk, iron/ironing board, travel crib

The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (61 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 CA $116
CA $224 total
includes taxes & fees
May 18 - May 19
The Farmhouse Loft "Greene County's Guesthouse"
Dining

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, (30 reviews)
"Yes, everything was very nice"
United States
Cary W.
The price is CA $143
CA $181 total
includes taxes & fees
May 26 - May 27
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Exterior

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is CA $244
CA $293 total
includes taxes & fees
May 8 - May 9
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Exterior

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (167 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is CA $89
CA $101 total
includes taxes & fees
May 10 - May 11
Knights Inn Jacksonville East Morton Ave
Interior

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Pleasant Hill
The price is CA $176
CA $251 total
includes taxes & fees
May 14 - May 15
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Dining

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, (18 reviews)
"Always a nice place to stay."
United States
Pete D.
The price is CA $135
CA $172 total
includes taxes & fees
May 25 - May 26
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior

Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo

Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
Nebo
10.0 out of 10, Exceptional, (3 reviews)
"A beautiful setting for some time away!"
United States
Amber S.
The price is CA $272
CA $571 total
includes taxes & fees
May 9 - May 10
Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
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
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
Anonymous traveller 4-night trip
Posted 1 hour ago
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

Find out more about Winchester

Winchester B&B information

Number of reviews
4,512
Accommodation
1 B&B
Lowest Price
CA $87
Highest Price
CA $571

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?
Check out this B&B in the surrounding 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 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.

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