A historic building with a clock tower, a statue, and well-maintained gardens.

Find a Bed and Breakfast in Winchester from CA $73

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A golf course with a pond, trees, and a clear sky.

1. Randolph Inn and Suites

Randolph Inn and Suites
2.5 star property
Winchester
8.8 out of 10, Excellent, (289 reviews)
"Loved the food"
United States
Sheri
The price is CA $136
CA $153 total
includes taxes & fees
Nov 15 - Nov 16
Randolph Inn and Suites
A buffet with various food items, including omelets and other dishes, served in metal containers.

2. Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG
2.5 star property
Portland
9.2 out of 10, Wonderful, (397 reviews)
"Always enjoy the Holiday Inn experience"
United States
Mary
The price is CA $154
CA $173 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Portland by IHG
A hotel room with a large bed, a desk with a computer, a chair, and a TV.

3. Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
2.5 star property
Richmond
8.6 out of 10, Excellent, (1,000 reviews)
"Staff was very helpful , had a problem with the bath and fixed quickly . The man at the breakfast was very helpful and friendly."
United States
James
The price is CA $107
CA $120 total
includes taxes & fees
Nov 8 - Nov 9
Baymont by Wyndham Richmond I-70
A hotel room with two beds, a desk with a TV, a dresser, and a window with curtains.

4. Motel 6 Portland, IN

Motel 6 Portland, IN
2.0 star property
Portland
7.2 out of 10, Good, (129 reviews)
"Clean room, nice staff and peaceful stay"
United States
Tommy
The price is CA $88
CA $99 total
includes taxes & fees
Nov 18 - Nov 19
Motel 6 Portland, IN
A hotel room with two beds, each with a purple bedspread and white pillows. There are framed artworks on the walls and a nightstand with a lamp between the beds.

5. Hoosier Inn

Hoosier Inn
2.5 star property
Portland
8.8 out of 10, Excellent, (147 reviews)
"Staff was very helpful. Will stay again."
United States
Deron
The price is CA $110
CA $123 total
includes taxes & fees
Dec 8 - Dec 9
Hoosier Inn
A hotel room with a large bathtub, a double bed, a desk, and a chair.

6. Quality Inn Greenville North

Quality Inn Greenville North
2.5 star property
Greenville
8.2 out of 10, Very good, (391 reviews)
"I enjoyed our stay, however the door to room was hard for us to open and the bathroom in room needs remodeling. Breakfast was good. The staff were friendly"
United States
Janell
The price is CA $126
CA $143 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Greenville North
A reception desk with a blue and white color scheme, a logo for 'SureStay by BEST WESTERN', and a geometric patterned wall.

7. Surestay By Best Western Greenville

Surestay By Best Western Greenville
2.5 star property
Greenville
7.8 out of 10, Good, (459 reviews)
"Place is clean and have stayed there before."
United States
don
The price is CA $129
CA $146 total
includes taxes & fees
Nov 15 - Nov 16
Surestay By Best Western Greenville
A building with a stone facade, a glass entrance, and a 'Lobby' sign.

8. Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
2.0 star property
Richmond
7.0 out of 10, Good, (982 reviews)
"No complaints. Decent place to stay at"
United States
Jeff
The price is CA $65
CA $73 total
includes taxes & fees
Dec 1 - Dec 2
Red Roof Inn Richmond, IN
A modern bistro bar with a wooden counter, a refrigerated display, and a menu board.

9. Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center
3.0 star property
Muncie
9.0 out of 10, Wonderful, (951 reviews)
"Would stay there again"
United States
Jennifer
The price is CA $143
CA $160 total
includes taxes & fees
Nov 22 - Nov 23
Courtyard Muncie at Horizon Convention Center
An outdoor patio with grey sofas, a circular stone fire pit, and a pergola with string lights.

10. Comfort Suites Richmond East

Comfort Suites Richmond East
2.5 star property
Richmond
9.4 out of 10, Exceptional, (899 reviews)
"Room was clean, check in friendly and efficient, breakfast was fine"
United States
Harley
The price is CA $139
CA $158 total
includes taxes & fees
Nov 29 - Nov 30
Comfort Suites Richmond East
A hotel room with three beds, a desk, and a chair. There are paintings on the walls and a window with curtains.

11. Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond
2.0 star property
Centerville
6.2 out of 10, (373 reviews)
"property itself is mostly maintained but the entrance road (and shops and gas station) was hazardous. Staff was pleasant and good."
United States
Ken
The price is CA $74
CA $83 total
includes taxes & fees
Nov 15 - Nov 16
Super 8 by Wyndham Centerville-Richmond
A modern hotel lobby with green seating, a reception desk, and a dining area in the background.

12. Holiday Inn Express Hotel & Suites Greenville by IHG

Holiday Inn Express Hotel & Suites Greenville by IHG
2.5 star property
Greenville
8.6 out of 10, Excellent, (354 reviews)
"Clean and everyone was super friendly."
United States
Kathryn
The price is CA $147
CA $166 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Hotel & Suites Greenville by IHG
A reception desk with a "Welcome to Richmond" sign, a plant, and a snack bar in the background.

13. Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70
2.5 star property
Richmond
8.6 out of 10, Excellent, (1,002 reviews)
"Great hotel for a quick stop. Rooms spacious and clean. Free breakfast also very good!"
United States
Kelly
The price is CA $131
CA $147 total
includes taxes & fees
Dec 6 - Dec 7
Best Western Plus Richmond Indiana I-70
Living area

14. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
6.0 out of 10, (2 reviews)
"Our second stay for a family cemetery project.Nice safety improvements since we visited - a railing on the steps to the second floor, a grab bar and mat for the tub.The atmosphere feels homey despite some quirks as a result of the home’s age.Easy stay."
United States
Robert Toy
The price is CA $108
CA $443 total
includes taxes & fees
Nov 19 - Nov 20
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Interior

15. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is CA $151
CA $458 total
includes taxes & fees
Dec 6 - Dec 7
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A hotel room with two beds, a TV, a dresser, a bench, and a mirror.

16. The Golden Inn

The Golden Inn
2.5 star property
New Paris
9.2 out of 10, Wonderful, (477 reviews)
"It was a very nice, clean and peaceful place to staff. The staff were very friendly too."
United States
Lynzee
The price is CA $111
CA $125 total
includes taxes & fees
Dec 7 - Dec 8
The Golden Inn
A modern hotel room with a lofted ceiling, a brick accent wall, a sofa, a coffee table, a desk, a chair, and a bed.

17. Best Western Muncie

Best Western Muncie
2.5 star property
Muncie
7.6 out of 10, Good, (897 reviews)
"Room was clean and staff was nice."
United States
Kalea
The price is CA $118
CA $132 total
includes taxes & fees
Dec 6 - Dec 7
Best Western Muncie
An outdoor seating area with fire pits and modern furniture, overlooking a street with buildings and a sunset view.

18. Home2 Suites By Hilton Muncie

Home2 Suites By Hilton Muncie
3.0 star property
Muncie
9.4 out of 10, Exceptional, (106 reviews)
"It was close to our wedding venue and it had everything we needed staff was superb ♥️♥️"
United States
Doris
The price is CA $166
CA $185 total
includes taxes & fees
Dec 6 - Dec 7
Home2 Suites By Hilton Muncie
A hotel room with a large bed, a smaller bed, a nightstand, a lamp, and a window with curtains.

19. Quality Inn and Conference Center

Quality Inn and Conference Center
2.5 star property
Richmond
6.6 out of 10, (1,001 reviews)
"Older hotel, really showing its age. Musty smell throughout the facility."
United States
Scott
The price is CA $76
CA $85 total
includes taxes & fees
Dec 6 - Dec 7
Quality Inn and Conference Center
A spacious lobby with a wooden staircase, a chandelier, and a reception desk.

20. Motel 6 Richmond, IN

Motel 6 Richmond, IN
2.0 star property
Richmond
8.2 out of 10, Very good, (1,003 reviews)
"Good stay for the price. Convenient location."
United States
Michael
The price is CA $73
CA $82 total
includes taxes & fees
Nov 19 - Nov 20
Motel 6 Richmond, IN
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 & Suites Muncie

Hampton Inn & Suites Muncie

10/10 Excellent
"Newly remodeled, very clean nice, hot breakfast, nice staff. I will definitely recommend"
John 1-night trip
Posted 19 hours ago
Hampton Inn & Suites Muncie

Find out more about Winchester

Winchester B&B information

Number of reviews
6,111
Accommodation
0 B&B
Lowest Price
CA $73
Highest Price
CA $458

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're traveling solo and hoping to get some tips from locals, a B&B can be a good choice for many different types of travelers. If you're interested in playing some golf on your trip, Winchester Golf Club is a good spot to tee off.
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 delectable breakfasts, B&Bs offer a truly one-of-a-kind environment.
When is the best time to stay at a B&B in Winchester?
When you're dreaming of a stay in 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 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Winchester is 47 inches.
What is there to do in Winchester?
If you're looking for some activities to entertain you on your trip, consider visiting Winchester Speedway and Winchester Golf Club. You might also consider a trip to sites like Levi Coffin House or Prairie Creek Reservoir and Campground if you have time to see more of the area.
How can I get to and around Winchester?
Planning your excursions in and around Winchester is easier with these transportation options. Fly into Muncie, IN (MIE-Delaware County), which is located 21.9 mi (35.2 km) away from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.

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