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Recommended hotels in Winchester
1. Randolph Inn and Suites
Randolph Inn and SuitesWinchester
8.8 out of 10, Excellent, (289 reviews)
"Loved the food"
Sheri
$108 nightly
The price is $121
Nov 6 - Nov 7
Total with taxes and fees
2. Holiday Inn Express & Suites Portland by IHG
Holiday Inn Express & Suites Portland by IHGPortland
9.2 out of 10, Wonderful, (396 reviews)
"Always enjoy the Holiday Inn experience"
Mary
$110 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
3. Baymont by Wyndham Richmond I-70
Baymont by Wyndham Richmond I-70Richmond
8.6 out of 10, Excellent, (1,008 reviews)
"Breakfast was the best and the staff member was terrific. He even offered to make us fried eggs if we did not want scrambled."
Ronald
$76 nightly
The price is $85
Nov 8 - Nov 9
Total with taxes and fees
4. Motel 6 Portland, IN
Motel 6 Portland, INPortland
7.2 out of 10, Good, (129 reviews)
"Clean room, nice staff and peaceful stay"
Tommy
$63 nightly
The price is $71
Nov 8 - Nov 9
Total with taxes and fees
5. Hoosier Inn
Hoosier InnPortland
8.8 out of 10, Excellent, (147 reviews)
"Staff was very helpful. Will stay again."
Deron
$73 nightly
The price is $82
Nov 8 - Nov 9
Total with taxes and fees
6. Surestay By Best Western Greenville
Surestay By Best Western GreenvilleGreenville
7.8 out of 10, Good, (459 reviews)
"Place is clean and have stayed there before."
don
$92 nightly
The price is $104
Nov 12 - Nov 13
Total with taxes and fees
7. Quality Inn Greenville North
Quality Inn Greenville NorthGreenville
8.2 out of 10, Very good, (390 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"
Janell
$89 nightly
The price is $101
Nov 29 - Nov 30
Total with taxes and fees
8. Red Roof Inn Richmond, IN
Red Roof Inn Richmond, INRichmond
7.0 out of 10, Good, (982 reviews)
"No complaints. Decent place to stay at"
Jeff
$46 nightly
The price is $52
Dec 1 - Dec 2
Total with taxes and fees
9. Super 8 by Wyndham Centerville-Richmond
Super 8 by Wyndham Centerville-RichmondCenterville
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."
Ken
$52 nightly
The price is $58
Nov 15 - Nov 16
Total with taxes and fees
10. Pets Welcome! Quiet Economy Home w/ Spacious Yard
Pets Welcome! Quiet Economy Home w/ Spacious YardEconomy
$292 nightly
The price is $326
Nov 8 - Nov 9
Total with taxes and fees
11. Pets Welcome! Quiet Economy Home w/ Spacious Yard
Pets Welcome! Quiet Economy Home w/ Spacious YardEconomy
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."
Robert Toy
$285 nightly
The price is $319
Nov 8 - Nov 9
Total with taxes and fees
12. Holiday Inn Express Hotel & Suites Greenville by IHG
Holiday Inn Express Hotel & Suites Greenville by IHGGreenville
8.6 out of 10, Excellent, (354 reviews)
"Clean and everyone was super friendly."
Kathryn
$104 nightly
The price is $118
Dec 4 - Dec 5
Total with taxes and fees
13. Courtyard Muncie at Horizon Convention Center
Courtyard Muncie at Horizon Convention CenterMuncie
9.0 out of 10, Wonderful, (950 reviews)
"Would stay there again"
Jennifer
$110 nightly
The price is $123
Nov 12 - Nov 13
Total with taxes and fees
14. New Hagerstown Apartment - Self Check-in. Sleeps 4+
New Hagerstown Apartment - Self Check-in. Sleeps 4+Hagerstown
9.4 out of 10, Exceptional, (28 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
Emily E.
$118 nightly
The price is $132
Nov 17 - Nov 18
Total with taxes and fees
15. Comfort Suites Richmond East
Comfort Suites Richmond EastRichmond
9.4 out of 10, Exceptional, (896 reviews)
"Nice breakfast."
Pamela
$100 nightly
The price is $112
Nov 29 - Nov 30
Total with taxes and fees
16. Days Inn by Wyndham Muncie -Ball State University
Days Inn by Wyndham Muncie -Ball State UniversityMuncie
7.0 out of 10, Good, (987 reviews)
"Raj was helpful at the front desk and available when needed. We also enjoyed watching the turtle in the lobby."
Matthew
$59 nightly
The price is $66
Nov 22 - Nov 23
Total with taxes and fees
17. Motel 6 Richmond, IN
Motel 6 Richmond, INRichmond
8.2 out of 10, Very good, (1,008 reviews)
"Good stay for the price. Convenient location."
Michael
$58 nightly
The price is $65
Dec 3 - Dec 4
Total with taxes and fees
18. Best Western Plus Richmond Indiana I-70
Best Western Plus Richmond Indiana I-70Richmond
8.6 out of 10, Excellent, (1,001 reviews)
"Great hotel for a quick stop. Rooms spacious and clean. Free breakfast also very good!"
Kelly
$93 nightly
The price is $105
Dec 3 - Dec 4
Total with taxes and fees
19. Super 8 by Wyndham Muncie/Ball St. College Area
Super 8 by Wyndham Muncie/Ball St. College AreaMuncie
8.0 out of 10, Very good, (1,006 reviews)
"Hotel is in a great location to Ball State University and restaurants. It was quiet and parking was great with various doors to access the hotel."
Duane
$59 nightly
The price is $66
Nov 22 - Nov 23
Total with taxes and fees
20. Quality Inn and Conference Center
Quality Inn and Conference CenterRichmond
6.6 out of 10, (1,001 reviews)
"Older hotel, really showing its age. Musty smell throughout the facility."
Scott
$54 nightly
The price is $60
Dec 1 - Dec 2
Total with taxes and fees
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.
Learn more about Winchester
In the heart of small-town America, Winchester's Historic Shopping & Dining District invites visitors to explore local heritage while savoring hometown flavors. Racing enthusiasts can catch high-octane action at Winchester Speedway, while golfers enjoy peaceful rounds at the well-maintained Winchester Golf Club.
Top reviews in Winchester
Randolph Inn and Suites
Randolph Inn and SuitesWinchester
10/10 Excellent
Randolph Inn is in a nice area. The rooms are clean and well maintained. Hotel staff in all areas were friendly and helpful. The morning breakfast made a good start to the day. The pool was clean and towels provided. We have stayed here several times over the years.
Tracy
