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Hotels in Winchester

November 2026
December 2026

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Oct 30 - Nov 1
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Nov 6 - Nov 8

Where to stay in Winchester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester hotels consistently deliver on quality, location and traveler experience. Last updated on October 26, 2026.
A living room with a fireplace, a television mounted above it, and a carpeted floor.
A golf course with a pond, trees, and a clear sky.
A kitchenette with a refrigerator, coffee machine, and a microwave. There is a sign indicating a meeting room.
An indoor swimming pool with clear water, a white chair, and windows allowing natural light.

1. Randolph Inn and Suites

Randolph Inn and Suites
Winchester
CNY648
CNY726 total
includes taxes & fees
Oct 26 - Oct 27
Randolph Inn and Suites
A modern bathroom with a toilet, a shower area, and a vanity with a mirror.
A spacious indoor area with multiple seating arrangements, including tables and chairs, and large windows offering views of the outdoors.
A gym with cardio machines, a pool, and large windows offering a view of the outdoors.
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
Portland
CNY734
CNY822 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express & Suites Portland by IHG
A hotel room with a large bed, a desk with a computer, a chair, and a TV.
A reception area with a stone wall, a reception desk, and a seating area with patterned chairs.
A living room with a fireplace, a flat-screen TV, and patterned sofas.
A narrow hallway with a microwave and trash bin on the left, leading to a door with a sign.

3. Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
Richmond
CNY516
CNY578 total
includes taxes & fees
Nov 2 - Nov 3
Baymont by Wyndham Richmond I-70
An outdoor seating area with fire pits and modern furniture, overlooking a street with buildings and a sunset view.
An indoor swimming pool with yellow chairs and tables, a blue ceiling, and a sign reading "POOLSIDE IS MY VIBE".
A modern hotel with a prominent "HOME 2" sign, multiple floors, and a well-lit entrance area.
A modern hotel room with two beds, a desk with a computer, a chair, and a television.

4. Home2 Suites By Hilton Muncie

Home2 Suites By Hilton Muncie
Muncie
CNY788
CNY883 total
includes taxes & fees
Nov 8 - Nov 9
Home2 Suites By Hilton Muncie
A reception desk with a blue and white color scheme, a logo for 'SureStay by BEST WESTERN', and a geometric patterned wall.
A room with multiple wooden tables and benches, a pool table, and a green arcade machine.
A covered outdoor area with a stone bench and grill, surrounded by a paved patio and a stone wall.
A spacious dining area with multiple tables and chairs, a kitchen counter with appliances, and a painting on the wall.

5. Surestay By Best Western Greenville

Surestay By Best Western Greenville
Greenville
CNY614
CNY695 total
includes taxes & fees
Oct 31 - Nov 1
Surestay By Best Western Greenville
A hotel room with a large bathtub, a double bed, a desk, and a chair.
A large indoor swimming pool with wooden walls and arched windows.
A living room with a fireplace, a sofa, a chair, a coffee table, and a staircase.
A gym with multiple rows of dumbbells on racks, a blue trash bin, and a red chair.

6. Quality Inn Greenville North

Quality Inn Greenville North
Greenville
CNY642
CNY727 total
includes taxes & fees
Nov 22 - Nov 23
Quality Inn Greenville North
An outdoor patio with grey sofas, a circular stone fire pit, and a pergola with string lights.
A Comfort Suites hotel with a modern design, featuring a prominent blue and white color scheme, a well-lit entrance, and a parking lot with several cars.
A modern reception desk with a wooden panel backdrop, a crescent-shaped light fixture, and a refrigerator stocked with beverages.
A modern hotel room with a bed, sofa, desk, and a round orange table.

7. Comfort Suites Richmond East

Comfort Suites Richmond East
Richmond
CNY780
CNY887 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Suites Richmond East
A hotel room with two beds, a desk, a chair, a TV, and a large window with curtains.
A modern bar area with a wooden counter, bar stools, and a menu board above.
A modern bistro bar with a wooden counter, a refrigerated display, and a menu board.
A circular outdoor seating area with a fire pit, surrounded by wicker chairs and a brick wall.

8. Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center
Muncie
CNY788
CNY883 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard Muncie at Horizon Convention Center
A modern hotel lobby with seating areas, tables, and artwork on the walls.
A snack display area with various packaged snacks and a refrigerated section with frozen goods.
A hotel room with a kitchenette, a flat-screen TV, a sofa, and a large window.
A hotel room with two beds, a TV, a wooden dresser, and a door leading to another room.

9. Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
Richmond
CNY815
CNY913 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn & Suites Richmond, IN
A hotel room with two beds, a desk with a TV, a dresser, and a window with curtains.
A gym with exercise equipment, a potted plant, and a window with blinds.
A reception desk with a wooden counter, a clock, and a no-smoking sign.
Two vending machines with snack options and a drink dispenser.

10. Motel 6 Portland, IN

Motel 6 Portland, IN
Portland
CNY420
CNY470 total
includes taxes & fees
Oct 28 - Oct 29
Motel 6 Portland, IN
A modern kitchen with a stone accent wall, a black countertop, and a wooden dining area with chairs.
An indoor swimming pool with clear water, surrounded by yellow chairs and a tiled floor.
A hotel reception area with a desk, two blue armchairs, a colorful carpet, and a sign reading "Connect & Print".
A Fairfield Inn Marriott hotel with a modern facade, a well-lit entrance, and a parking area with marked spaces.

11. Fairfield Inn by Marriott Muncie

Fairfield Inn by Marriott Muncie
Muncie
CNY684
CNY766 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn by Marriott Muncie
A modern hotel lobby with green seating, a reception desk, and a dining area in the background.
A hotel room with a large bed, bedside tables, a chair, and a desk.
A buffet with various food items in metal containers, a coffee station, and a sign indicating a vegetarian omelet option.
A modern office space with a reception area, multiple workstations, and comfortable seating.

12. Holiday Inn Express Hotel & Suites Greenville by IHG

Holiday Inn Express Hotel & Suites Greenville by IHG
Greenville
CNY734
CNY831 total
includes taxes & fees
Oct 31 - Nov 1
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.
An outdoor patio with a fire feature, seating, and a view into the interior.
A modern indoor pool area with lounge chairs, a pool table, and a reception desk.
A modern dining area with a large table and chairs, large windows with a view of trees, and a neon sign on the wall.

13. Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70
Richmond
CNY624
CNY698 total
includes taxes & fees
Nov 2 - Nov 3
Best Western Plus Richmond Indiana I-70
An outdoor patio with yellow chairs and tables, a wooden ceiling with lights, and a view of buildings in the background.
A modern hotel with a covered entrance, large windows, and a sign indicating it is a Home2 Suites location.
A hotel room with a bed, a sofa, a small ottoman, a nightstand with a lamp, and a wall-mounted picture.
A modern hotel lobby with a seating area, a TV, and a reception desk.

14. Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond
Richmond
CNY815
CNY913 total
includes taxes & fees
Nov 8 - Nov 9
Home2 Suites by Hilton Richmond
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.
A motel with a brick facade, multiple balconies, and a parking lot with several vehicles.
A compact room with a microwave on a small black appliance, a blue ironing board, a lamp, and a wall-mounted ironing board.
A television on a wooden dresser in a hotel room.

15. Hoosier Inn

Hoosier Inn
Portland
CNY540
CNY605 total
includes taxes & fees
Oct 27 - Oct 28
Hoosier Inn
Room
A modern hotel room with a lofted ceiling, a brick accent wall, a sofa, a coffee table, a desk, a chair, and a bed.
A hotel room with a sofa, a desk with a chair, a television, and a window with curtains.
A modern interior with a sectional sofa, round coffee table, and wicker chairs.

16. Best Western Muncie

Best Western Muncie
Muncie
CNY595
CNY667 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Muncie
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
A reception area with a stone wall, a clock, and a digital kiosk.
A hotel room with a blue sofa, a wooden coffee table, a small side table, and a bed with a brown blanket.
A breakfast bar with various food items and kitchen appliances.

17. Comfort Inn & Suites Muncie Near University

Comfort Inn & Suites Muncie Near University
Muncie
CNY609
CNY683 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Muncie Near University
A building with a stone facade, a glass entrance, and a 'Lobby' sign.
A Red Roof Inn lobby with a stone wall, two leather chairs, a flat-screen TV, a Red Roof Plus sign, and a Red Roof coffee machine.
A coffee station with a coffee machine, disposable cups, and coffee creamer bottles.
A Red Roof Inn lobby with stone walls, a fireplace, leather chairs, and a flat-screen TV.

18. Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
Richmond
CNY315
CNY353 total
includes taxes & fees
Nov 1 - Nov 2
Red Roof Inn Richmond, IN
A modern dining area with a mix of seating options, including tables and booths, and a central bar area.
A hotel room with a kitchenette, a desk, a sofa, and a large window.
A modern indoor swimming pool with clear blue water, surrounded by lounge chairs and a poolside bar.
A hotel room with two beds, a desk with a TV, a mirror, a chair, and a microwave.

19. Hampton Inn & Suites Muncie

Hampton Inn & Suites Muncie
Muncie
CNY731
CNY819 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Muncie
A spacious lobby with a wooden staircase, a chandelier, and a reception desk.
A hotel lobby with a reception desk, a staircase, and a seating area with a table and chairs.
A staircase with wooden railings leading to a second-floor area.
A hotel lobby with two round tables, four chairs, a bar area with a glass partition, a clock on the wall, and a staircase in the background.

20. Motel 6 Richmond, IN

Motel 6 Richmond, IN
Richmond
CNY367
CNY411 total
includes taxes & fees
Nov 8 - Nov 9
Motel 6 Richmond, IN
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Go beyond your typical stay in Winchester

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Our prices for hotels in Winchester are cheapest in April

Price trends for hotels in Winchester

Pricing is based on two traveler single night rates
View properties in October

October

High 17°C / low 8°C. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Winchester

Winchester Speedway

7.8/10 (26 reviews)
You can catch an event at Winchester Speedway, located 2.5 mi (4 km) from central Winchester.
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Randolph County Courthouse

9.0/10 (2 reviews)
Randolph County Courthouse is worth a visit when in central Winchester.
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Winchester Golf Club

7.2/10 (13 reviews)
You might want to play some rounds at Winchester Golf Club, located 1.1 mi (1.8 km) from central Winchester.
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Learn more about Winchester

Winchester is well-known for its attractions such as Winchester Speedway and Winchester Golf Club.

See all hotels in Winchester
A historic building with a clock tower, a statue, and well-maintained gardens.

Check out reviews of Winchester hotels guests love

A living room with a fireplace, a television mounted above it, and a carpeted floor.
A golf course with a pond, trees, and a clear sky.
A kitchenette with a refrigerator, coffee machine, and a microwave. There is a sign indicating a meeting room.
An indoor swimming pool with clear water, a white chair, and windows allowing natural light.

Randolph Inn and Suites

Randolph Inn and Suites
Winchester

10/10 Exceptional

United States
Tracy
Randolph Inn and Suites
A modern bathroom with a toilet, a shower area, and a vanity with a mirror.
A spacious indoor area with multiple seating arrangements, including tables and chairs, and large windows offering views of the outdoors.
A gym with cardio machines, a pool, and large windows offering a view of the outdoors.
A buffet with various food items, including omelets and other dishes, served in metal containers.

Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG
Portland

10/10 Exceptional

United States
Anonymous traveler
Holiday Inn Express & Suites Portland by IHG
An outdoor patio with grey sofas, a circular stone fire pit, and a pergola with string lights.
A Comfort Suites hotel with a modern design, featuring a prominent blue and white color scheme, a well-lit entrance, and a parking lot with several cars.
A modern reception desk with a wooden panel backdrop, a crescent-shaped light fixture, and a refrigerator stocked with beverages.
A modern hotel room with a bed, sofa, desk, and a round orange table.

Comfort Suites Richmond East

Comfort Suites Richmond East
Richmond

10/10 Exceptional

United States
Kimberly
Comfort Suites Richmond East
A hotel room with a large bed, a desk with a computer, a chair, and a TV.
A reception area with a stone wall, a reception desk, and a seating area with patterned chairs.
A living room with a fireplace, a flat-screen TV, and patterned sofas.
A narrow hallway with a microwave and trash bin on the left, leading to a door with a sign.

Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
Richmond

10/10 Exceptional

United States
jason
Baymont by Wyndham Richmond I-70
A hotel room with two beds, a desk, a chair, a TV, and a large window with curtains.
A modern bar area with a wooden counter, bar stools, and a menu board above.
A modern bistro bar with a wooden counter, a refrigerated display, and a menu board.
A circular outdoor seating area with a fire pit, surrounded by wicker chairs and a brick wall.

Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center
Muncie

10/10 Exceptional

United States
Ron
Courtyard Muncie at Horizon Convention Center
An outdoor patio with yellow chairs and tables, a wooden ceiling with lights, and a view of buildings in the background.
A modern hotel with a covered entrance, large windows, and a sign indicating it is a Home2 Suites location.
A hotel room with a bed, a sofa, a small ottoman, a nightstand with a lamp, and a wall-mounted picture.
A modern hotel lobby with a seating area, a TV, and a reception desk.

Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond
Richmond

10/10 Exceptional

United States
Chuck
Home2 Suites by Hilton Richmond
A modern hotel lobby with seating areas, tables, and artwork on the walls.
A snack display area with various packaged snacks and a refrigerated section with frozen goods.
A hotel room with a kitchenette, a flat-screen TV, a sofa, and a large window.
A hotel room with two beds, a TV, a wooden dresser, and a door leading to another room.

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
Richmond

10/10 Exceptional

United States
Anonymous traveler
Hampton Inn & Suites Richmond, IN
A hotel room with a large bathtub, a double bed, a desk, and a chair.
A large indoor swimming pool with wooden walls and arched windows.
A living room with a fireplace, a sofa, a chair, a coffee table, and a staircase.
A gym with multiple rows of dumbbells on racks, a blue trash bin, and a red chair.

Quality Inn Greenville North

Quality Inn Greenville North
Greenville

10/10 Exceptional

United States
Kyleen
Quality Inn Greenville North
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.
A motel with a brick facade, multiple balconies, and a parking lot with several vehicles.
A compact room with a microwave on a small black appliance, a blue ironing board, a lamp, and a wall-mounted ironing board.
A television on a wooden dresser in a hotel room.

Hoosier Inn

Hoosier Inn
Portland

10/10 Exceptional

United States
Rita
Hoosier Inn
A lobby with a stone wall, a coffee station, two green sofas, and a white table.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A corner market with refrigerated and non-refrigerated food sections, a vending machine, and a wall with informational posters.
A Fairfield Inn & Suites hotel with a covered parking area and a landscaped entrance.

Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond
New Paris

10/10 Exceptional

United States
Marie
Fairfield Inn by Marriott Richmond
A modern dining area with a mix of seating options, including tables and booths, and a central bar area.
A hotel room with a kitchenette, a desk, a sofa, and a large window.
A modern indoor swimming pool with clear blue water, surrounded by lounge chairs and a poolside bar.
A hotel room with two beds, a desk with a TV, a mirror, a chair, and a microwave.

Hampton Inn & Suites Muncie

Hampton Inn & Suites Muncie
Muncie

10/10 Exceptional

United States
Keturah
Hampton Inn & Suites Muncie
A reception desk with a "Welcome to Richmond" sign, a plant, and a snack bar in the background.
An outdoor patio with a fire feature, seating, and a view into the interior.
A modern indoor pool area with lounge chairs, a pool table, and a reception desk.
A modern dining area with a large table and chairs, large windows with a view of trees, and a neon sign on the wall.

Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70
Richmond

10/10 Exceptional

United States
Amy
Best Western Plus Richmond Indiana I-70
A hotel room with two beds, a TV, a dresser, a bench, and a mirror.
Bathroom
A hotel room with a bed, a desk, a chair, a lamp, and a painting on the wall.
A suburban street with a house, a 'No Parking' sign, and a utility pole.

The Golden Inn

The Golden Inn
New Paris

10/10 Exceptional

United States
donna
The Golden Inn
A modern kitchen with a stone accent wall, a black countertop, and a wooden dining area with chairs.
An indoor swimming pool with clear water, surrounded by yellow chairs and a tiled floor.
A hotel reception area with a desk, two blue armchairs, a colorful carpet, and a sign reading "Connect & Print".
A Fairfield Inn Marriott hotel with a modern facade, a well-lit entrance, and a parking area with marked spaces.

Fairfield Inn by Marriott Muncie

Fairfield Inn by Marriott Muncie
Muncie

10/10 Exceptional

United States
Tyrah
Fairfield Inn by Marriott Muncie
A hotel hallway with a sofa, a lamp, a TV, and a view into a bedroom.
A snack bar with shelves of chips and snacks, a refrigerated section with drinks and food, and a display of bottled water.
A reception area with two white reception desks, a blue and white geometric wall art, and a wooden accent wall.
A Holiday Inn Express hotel with a covered entrance, brick facade, and multiple windows.

Holiday Inn Express Richmond by IHG

Holiday Inn Express Richmond by IHG
Richmond

10/10 Exceptional

United States
melissa
Holiday Inn Express Richmond by IHG

Frequently Asked Questions

How much does a hotel room cost in Winchester?

You can choose a great hotel in Winchester from CNY314 with properties to suit all budgets and needs. If you're after an affordable hotel in Winchester that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Winchester hotels?

Discover great deals on Winchester hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Winchester hotels.

Can I book Winchester hotels with free cancellation?

In order to book a refundable Winchester hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some of the best Winchester hotels with free parking?

If you're arriving by car, choosing a great Winchester hotel with free parking is a plus. Our travelers' favorites include:

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