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Find a Bed and Breakfast in Winchester from CA $87

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16
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
7.6 out of 10, Good, (24 reviews)
"If you want basic hotel services, this works. It was clean. Doors locked, shower had hot water, there's a few cold items for breakfast."
United States
Tammy
The price is CA $78
CA $87 total
includes taxes & fees
Jul 5 - Jul 6
Jacksonville Inn & Suites
Indoor pool

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (805 reviews)
"The pool area is cozy and clean! Employees are nice, breakfast is good 🙂 love the room w pool view"
United States
Alaric
The price is CA $85
CA $97 total
includes taxes & fees
Jun 25 - Jun 26
Best Western Jacksonville Inn
Breakfast meal

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (364 reviews)
"Staff was great. Food in the restaurant is very good and drinks."
United States
Beth
The price is CA $111
CA $123 total
includes taxes & fees
Jul 10 - Jul 11
William Watson Hotel
Free daily continental breakfast

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (147 reviews)
"Good place to stay!"
United States
Riley
The price is CA $167
CA $183 total
includes taxes & fees
Jun 23 - Jun 24
Green Acres Hotel
Hallway

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (65 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 $138
CA $152 total
includes taxes & fees
Jun 22 - Jun 23
Monroe Street Suites
Free daily on-the-go breakfast

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (139 reviews)
"Staff is great and id stay again "
United States
Thor
The price is CA $86
CA $94 total
includes taxes & fees
Jul 14 - Jul 15
Rodeway Inn Pittsfield
Exterior

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (701 reviews)
"clean room and breakfast, descent parking, stayed here a lot during business trips"
United States
Keith
The price is CA $131
CA $145 total
includes taxes & fees
Jul 19 - Jul 20
Sleep Inn & Suites South Jacksonville
Restaurant

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (526 reviews)
"Clean it’s ok for a nights stay"
United States
Mike
The price is CA $129
CA $147 total
includes taxes & fees
Jun 28 - Jun 29
Hampton Inn 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, (647 reviews)
"A great place to stay. Everything was great"
United States
William
The price is CA $83
CA $95 total
includes taxes & fees
Jun 28 - Jun 29
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, (475 reviews)
"The rooms were ok. A/C worked good & beds were comfortable. TV was very small, bathroom floor was very wrapped with old dirty stick tile. Complimentary refillable shower & sink containers needed cleaned. Breakfast started at 7am, too late for my kids to grab a bite before we had to leave for our early ballgame."
United States
Julie
The price is CA $146
CA $162 total
includes taxes & fees
Jun 28 - Jun 29
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, (172 reviews)
"Very clean , washer and dryer available ! "
United States
Stacy
The price is CA $92
CA $105 total
includes taxes & fees
Jun 22 - Jun 23
Knights Inn Jacksonville East Morton Ave
Lobby

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (478 reviews)
"Overall good place to stay"
United States
Mark
The price is CA $96
CA $106 total
includes taxes & fees
Jun 30 - Jul 1
Quality Inn Jacksonville near I-72
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, (14 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is CA $183
CA $223 total
includes taxes & fees
Jul 5 - Jul 6
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
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, (66 reviews)
"We had such a great experience staying here. The property was beautiful and the hosts were very welcoming and friendly. The property was very pet friendly as well. We will definitely go back for the peace and quiet!"
United States
Mandy S.
The price is CA $174
CA $215 total
includes taxes & fees
Jul 8 - Jul 9
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
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 $120
CA $232 total
includes taxes & fees
Jun 28 - Jun 29
The Farmhouse Loft "Greene County's Guesthouse"
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 $183
CA $262 total
includes taxes & fees
Jun 28 - Jun 29
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Exterior

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (62 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is CA $253
CA $302 total
includes taxes & fees
Jun 29 - Jun 30
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
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)
"Super easy access, great little place with everything I needed. It's too bad I was staying in winter, because I bet it's super nice when everything is blooming and the bees are buzzing. "
United States
Tanya A.
The price is CA $161
CA $201 total
includes taxes & fees
Jul 15 - Jul 16
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
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, (4 reviews)
"Host is super friendly and responds quickly, was very clean and spacious. Will be staying at again in the future!"
United States
Aaron G.
The price is CA $283
CA $597 total
includes taxes & fees
Jun 24 - Jun 25
Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
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, (19 reviews)
"Always a nice place to stay."
United States
Pete D.
The price is CA $140
CA $178 total
includes taxes & fees
Jun 30 - Jul 1
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
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

William Watson Hotel

William Watson Hotel

10/10 Excellent
"The check-in process was extremely easy. The atmosphere was wonderful, clean rooms, we loved everything about the hotel!"
Deanna 1-night trip
Posted 23 hours ago
William Watson Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
4,543
Accommodation
1 B&B
Lowest Price
CA $87
Highest Price
CA $183

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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