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Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Golf
Randolph Inn and Suites

Randolph Inn and Suites

Randolph Inn and Suites
2.5 star property
Winchester
9.0 out of 10, Wonderful, (245)
"Nice hotel"
United States
William
$108 nightly
The price is $121
Dec 21 - Dec 22
Total with taxes and fees
Randolph Inn and Suites
Room, 1 King Bed, Accessible, Non Smoking (Mobility, Bathtub w/Grab Bars) | Iron/ironing board, free cribs/infant beds, free WiFi, bed sheets
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
2.5 star property
Richmond
8.4 out of 10, Very Good, (1001)
"Breakfast was fresh and good "
United States
Brian
$67 nightly
The price is $75
Dec 21 - Dec 22
Total with taxes and fees
Baymont by Wyndham Richmond I-70
Reception
Richmond Inn & Suites

Richmond Inn & Suites

Richmond Inn & Suites
2.0 star property
Richmond
7.0 out of 10, Good, (360)
"Good staff good stay"
United States
Terrance
$51 nightly
The price is $55
Dec 21 - Dec 22
Total with taxes and fees
Richmond Inn & Suites
Standard 2 Queens Non Smoking | Desk, blackout drapes, soundproofing, iron/ironing board
Quality Inn and Conference Center

Quality Inn and Conference Center

Quality Inn and Conference Center
2.5 star property
Richmond
6.6 out of 10, (1000)
"nice place to stay"
United States
Onda
$43 nightly
The price is $48
Jan 15 - Jan 16, 2026
Total with taxes and fees
Quality Inn and Conference Center
Exterior
Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
2.0 star property
Richmond
7.0 out of 10, Good, (913)
"Room was clean, staff friendly "
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Rolin
$47 nightly
The price is $52
Dec 28 - Dec 29
Total with taxes and fees
Red Roof Inn Richmond, IN
Free WiFi, bed sheets
Motel 6 Richmond, IN

Motel 6 Richmond, IN

Motel 6 Richmond, IN
2.0 star property
Richmond
7.8 out of 10, Good, (1002)
"Yes the room was clean the staff was helpful and courteous and informative about the festivities that were going on in town"
United States
James
$57 nightly
The price is $64
Dec 21 - Dec 22
Total with taxes and fees
Motel 6 Richmond, IN
Standard Room, 1 King Bed, Non Smoking | Desk, blackout drapes, soundproofing, iron/ironing board
Hoosier Inn

Hoosier Inn

Hoosier Inn
2.5 star property
Portland
8.8 out of 10, Excellent, (134)
"Had a pleasant stay. Room was very clean and staff was very friendly. "
United States
ned
$81 nightly
The price is $91
Dec 22 - Dec 23
Total with taxes and fees
Hoosier Inn
Studio Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond
2.0 star property
Centerville
6.0 out of 10, (332)
"Nice managed motel. Will definitely be staying here again. "
United States
Kenny
$44 nightly
The price is $49
Jan 19 - Jan 20, 2026
Total with taxes and fees
Super 8 by Wyndham Centerville-Richmond
Front of property
The Golden Inn

The Golden Inn

The Golden Inn
2.5 star property
New Paris
9.2 out of 10, Wonderful, (433)
"Wonderful place to stay, clean rooms and quiet, very comfortable, would stay here again so nice."
United States
Renee
$85 nightly
The price is $96
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Golden Inn
Desk, laptop workspace, iron/ironing board, free WiFi
Travelodge by Wyndham Richmond IN

Travelodge by Wyndham Richmond IN

Travelodge by Wyndham Richmond IN
2.0 star property
Richmond
7.0 out of 10, Good, (440)
"Nice place and staff. "
United States
Russell
$53 nightly
The price is $59
Jan 4 - Jan 5, 2026
Total with taxes and fees
Travelodge by Wyndham Richmond IN
Lobby
Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond
2.5 star property
New Paris
9.0 out of 10, Wonderful, (517)
"The room was clean, the staff was polite and friendly. "
United States
Leslie
$93 nightly
The price is $105
Dec 24 - Dec 25
Total with taxes and fees
Fairfield Inn by Marriott Richmond
Free daily on-the-go breakfast
Holiday Inn Express & Suites Portland by IHG

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, (354)
"Excellent stay every time we are there friendly staff all around awesome stay"
United States
Rebecca
$97 nightly
The price is $109
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn Express & Suites Portland by IHG
Exterior
Comfort Suites Richmond East

Comfort Suites Richmond East

Comfort Suites Richmond East
2.5 star property
Richmond
9.4 out of 10, Exceptional, (654)
"Room was clean, front desk was friendly. "
United States
Susan
$90 nightly
The price is $101
Dec 28 - Dec 29
Total with taxes and fees
Comfort Suites Richmond East
Lobby
Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70
2.5 star property
Richmond
8.4 out of 10, Very Good, (1000)
"New facility, best hotel I’ve stayed in recently!"
United States
Antonia
$85 nightly
The price is $95
Dec 28 - Dec 29
Total with taxes and fees
Best Western Plus Richmond Indiana I-70
Lobby
Surestay By Best Western Greenville

Surestay By Best Western Greenville

Surestay By Best Western Greenville
2.5 star property
Greenville
7.8 out of 10, Good, (381)
"Parking was good, room was clean but spatub didn’t work, area was clean and nice. Staff was great. But breakfast was subpar, no selection and can't even say its a continental breakfast. No protein only fruit and yogurt."
United States
Christina
$93 nightly
The price is $105
Dec 28 - Dec 29
Total with taxes and fees
Surestay By Best Western Greenville
Free daily buffet breakfast
Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
2.5 star property
Richmond
9.2 out of 10, Wonderful, (942)
"The breakfast service was excellent tasty and well presented "
United States
Terence
$98 nightly
The price is $109
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hampton Inn & Suites Richmond, IN
Interior
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie

The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Muncie
10.0 out of 10, Exceptional, (6)
"Excellent hospitality and accommodations!It was so nice to have snacks available waiting for us upon arrival. The ice and water options were so nice. We felt so at home in this safe, quiet neighborhood with discreet parking right at the door. Hope to book again when we come to visit our family. Easy access with personalized code provided from owner. Clean, great communication, had everything we needed.Thank you so much."
United States
Tamara B.
$145 nightly
The price is $163
Dec 29 - Dec 30
Total with taxes and fees
The Cardinal. Newly built 1-bedroom cottage w/ WiFi and AC in delightful Muncie
Exterior
Super 8 by Wyndham Muncie/Ball St. College Area

Super 8 by Wyndham Muncie/Ball St. College Area

Super 8 by Wyndham Muncie/Ball St. College Area
2.0 star property
Muncie
8.0 out of 10, Very Good, (1001)
"Room was good and staff was very kind"
United States
Nicolas
$59 nightly
The price is $66
Jan 4 - Jan 5, 2026
Total with taxes and fees
Super 8 by Wyndham Muncie/Ball St. College Area
Exterior
Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond
3.0 star property
Richmond
9.2 out of 10, Wonderful, (404)
"Very spacious room, great amenities, and delicious breakfast every morning!"
United States
Kiana
$93 nightly
The price is $104
Jan 4 - Jan 5, 2026
Total with taxes and fees
Home2 Suites by Hilton Richmond
Room, 1 King Bed, Non Smoking, Jetted Tub | Iron/ironing board, free WiFi, bed sheets, alarm clocks
Quality Inn Greenville North

Quality Inn Greenville North

Quality Inn Greenville North
2.5 star property
Greenville
8.2 out of 10, Very Good, (346)
"Our stay at the Quality Inn was good, it was clean, smelled clean, and the Breakfast options were very good, and at night it was quiet. "
United States
Gregg A
$106 nightly
The price is $120
Jan 2 - Jan 3, 2026
Total with taxes and fees
Quality Inn Greenville North
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

Baymont by Wyndham Muncie Near Ball State University

Baymont by Wyndham Muncie Near Ball State University

10/10 Excellent
"yes"
Brent 1-night trip
Posted 3 days ago
Baymont by Wyndham Muncie Near Ball State University

Find out more about Winchester

Winchester B&B information

Number of reviews
11,459
Accommodation
0 B&B
Lowest Price
$48
Highest Price
$163

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 Golf Club and Winchester Speedway. You might also consider a trip to sites like Prairie Creek Reservoir and Campground or Darke County Fairgrounds 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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