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Hotels in Winchester

October 2026
13
November 2026

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This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 14, 2026.
A golf course with a pond, trees, and a clear sky.
A kitchen with a granite countertop, a stainless steel sink, wooden cabinets, a coffee maker, and a trash can.
A kitchenette with a refrigerator, coffee machine, and a microwave. There is a sign indicating a meeting room.
A living room with a fireplace, a television mounted above it, and a carpeted floor.

1. Randolph Inn and Suites

Randolph Inn and Suites
Winchester
CNY651
CNY729 total
includes taxes & fees
Oct 14 - Oct 15
Randolph Inn and Suites
A spacious indoor area with multiple seating arrangements, including tables and chairs, and large windows offering views of the outdoors.
A modern hotel room with a desk, chairs, a computer, and a couch.
A gym with cardio machines, a pool, and large windows offering a view of the outdoors.
A Holiday Inn Express hotel with a covered entrance, brick facade, and a clear blue sky.

2. Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG
Portland
CNY736
CNY825 total
includes taxes & fees
Oct 18 - Oct 19
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 narrow hallway with a microwave and trash bin on the left, leading to a door with a sign.
A living room with a fireplace, a flat-screen TV, and patterned sofas.
A reception area with a stone wall, a reception desk, and a seating area with patterned chairs.

3. Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70
Richmond
CNY506
CNY567 total
includes taxes & fees
Oct 18 - Oct 19
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 room with two beds, a desk with a computer, a chair, and a television.
A modern hotel with a prominent "HOME 2" sign, multiple floors, and a well-lit entrance area.

4. Home2 Suites By Hilton Muncie

Home2 Suites By Hilton Muncie
Muncie
CNY848
CNY949 total
includes taxes & fees
Oct 25 - Oct 26
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 hotel room with a bed, a desk, a chair, two bedside tables with lamps, and a window with curtains.
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
CNY616
CNY698 total
includes taxes & fees
Oct 20 - Oct 21
Surestay By Best Western Greenville
A modern bistro bar with a wooden counter, a refrigerated display, and a menu board.
A modern bar area with a wooden counter, bar stools, and a menu board above.
A circular outdoor seating area with a fire pit, surrounded by wicker chairs and a brick wall.
A Courtyard by Marriott hotel with a modern facade, multiple floors, and a parking lot in front.

6. Courtyard Muncie at Horizon Convention Center

Courtyard Muncie at Horizon Convention Center
Muncie
CNY734
CNY822 total
includes taxes & fees
Oct 20 - Oct 21
Courtyard Muncie at Horizon Convention Center
An outdoor patio with grey sofas, a circular stone fire pit, and a pergola with string lights.
A modern hotel room with a bed, sofa, desk, and a round orange table.
A modern reception desk with a wooden panel backdrop, a crescent-shaped light fixture, and a refrigerator stocked with beverages.
A modern building with a blue-lit facade, a snow-covered ground, and a visible snow-clearing vehicle.

7. Comfort Suites Richmond East

Comfort Suites Richmond East
Richmond
CNY768
CNY873 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Suites Richmond East
A hotel room with a large bathtub, a double bed, a desk, and a chair.
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.
A hotel with a red roof, beige walls, and a central entrance with a sign.

8. Quality Inn Greenville North

Quality Inn Greenville North
Greenville
CNY648
CNY734 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Greenville North
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 Fairfield Inn Marriott hotel with a modern facade, a well-lit entrance, and a parking area with marked spaces.
A vending machine area with snacks and beverages.

9. Fairfield Inn by Marriott Muncie

Fairfield Inn by Marriott Muncie
Muncie
CNY717
CNY803 total
includes taxes & fees
Oct 20 - Oct 21
Fairfield Inn by Marriott Muncie
A reception desk with a "Welcome to Richmond" sign, a plant, and a snack bar in the background.
A modern indoor pool area with lounge chairs, a pool table, and a reception desk.
A mural with 'Rose City' prominently displayed, surrounded by various illustrated landmarks and attractions.
A modern dining area with a large table and chairs, large windows with a view of trees, and a neon sign on the wall.

10. Best Western Plus Richmond Indiana I-70

Best Western Plus Richmond Indiana I-70
Richmond
CNY626
CNY701 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Richmond Indiana I-70
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 swimming pool with lounge chairs and a blue wall.
A hotel room with a kitchenette, a flat-screen TV, a sofa, and a large window.

11. Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
Richmond
CNY820
CNY918 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn & Suites Richmond, IN
A modern hotel lobby with green seating, a reception desk, and a dining area in the background.
A modern lobby with seating areas, a flat-screen TV, and a decorative wall mural.
A modern office space with a reception area, multiple workstations, and comfortable seating.
A hotel room with a large bed, bedside tables, a chair, and a desk.

12. Holiday Inn Express Hotel & Suites Greenville by IHG

Holiday Inn Express Hotel & Suites Greenville by IHG
Greenville
CNY736
CNY834 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Hotel & Suites Greenville by IHG
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.
Two vending machines with snack options and a drink dispenser.
A two-story building with a brick facade, a covered entrance, and a clear sky.

13. Motel 6 Portland, IN

Motel 6 Portland, IN
Portland
CNY422
CNY472 total
includes taxes & fees
Oct 14 - Oct 15
Motel 6 Portland, IN
An outdoor patio with yellow chairs and tables, a wooden ceiling with lights, and a view of buildings in the background.
A modern hotel lobby with a central seating area featuring patterned chairs, a round table, and a chandelier.
A hotel room with a bed, a sofa, a small ottoman, a nightstand with a lamp, and a wall-mounted picture.
A modern hotel with a covered entrance, large windows, and a sign indicating it is a Home2 Suites location.

14. Home2 Suites by Hilton Richmond

Home2 Suites by Hilton Richmond
Richmond
CNY818
CNY916 total
includes taxes & fees
Oct 25 - Oct 26
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 television on a wooden dresser in a hotel room.
A compact room with a microwave on a small black appliance, a blue ironing board, a lamp, and a wall-mounted ironing board.
A bathroom with a toilet, a bathtub, and a shower curtain.

15. Hoosier Inn

Hoosier Inn
Portland
CNY542
CNY607 total
includes taxes & fees
Oct 18 - Oct 19
Hoosier Inn
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 compact kitchen with wooden cabinets, a microwave, a coffee maker, a dishwasher, and a granite countertop.

16. Comfort Inn & Suites Muncie Near University

Comfort Inn & Suites Muncie Near University
Muncie
CNY637
CNY714 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Muncie Near University
A hotel room with three beds, a desk, and a chair. There are paintings on the walls and a window with curtains.
A hotel room with a large mirror, a coffee machine, a clock, and a door with a curtain.
A motel with a Super 8 sign, large windows, a covered parking area, and a well-maintained lawn.
A hotel room with two beds, a desk, a TV, and a dresser.

17. Super 8 by Wyndham Centerville-Richmond

Super 8 by Wyndham Centerville-Richmond
Centerville
CNY361
CNY404 total
includes taxes & fees
Oct 25 - Oct 26
Super 8 by Wyndham Centerville-Richmond
A vending area with Coca-Cola and Pepsi machines.
A hotel room with a large bed, bedside lamps, a desk, an office chair, a window with curtains, and an air conditioning unit.
Exterior
An indoor swimming pool with a brick wall and wooden ceiling, surrounded by lounge chairs and a covered seating area.

18. Best Western Muncie

Best Western Muncie
Muncie
CNY597
CNY669 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Muncie
A lobby with a stone wall, a coffee station, two green sofas, and a white table.
A corner market with refrigerated and non-refrigerated food sections, a vending machine, and a wall with informational posters.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
A Fairfield Inn & Suites hotel with a covered parking area and a landscaped entrance.

19. Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond
New Paris
CNY762
CNY863 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn by Marriott Richmond
A hotel entrance with a stone facade, a covered entrance, and a ramp for accessibility.
A Red Roof Inn lobby with a stone fireplace, two leather chairs, a fire feature, and a sign indicating free Wi-Fi in all rooms.
A hotel room with a bed, a desk with a chair, a television, and a door.
Vending machines for Pepsi and an ice dispenser in a hotel corridor.

20. Red Roof Inn Richmond, IN

Red Roof Inn Richmond, IN
Richmond
CNY321
CNY360 total
includes taxes & fees
Oct 25 - Oct 26
Red Roof Inn 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.
See properties

Randolph County Courthouse

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

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.
See properties

Check out reviews of Winchester hotels guests love

A golf course with a pond, trees, and a clear sky.
A kitchen with a granite countertop, a stainless steel sink, wooden cabinets, a coffee maker, and a trash can.
A kitchenette with a refrigerator, coffee machine, and a microwave. There is a sign indicating a meeting room.
A living room with a fireplace, a television mounted above it, and a carpeted floor.

Randolph Inn and Suites

Randolph Inn and Suites
Winchester

10/10 Exceptional

United States
Tracy
Randolph Inn and Suites
A spacious indoor area with multiple seating arrangements, including tables and chairs, and large windows offering views of the outdoors.
A modern hotel room with a desk, chairs, a computer, and a couch.
A gym with cardio machines, a pool, and large windows offering a view of the outdoors.
A Holiday Inn Express hotel with a covered entrance, brick facade, and a clear blue sky.

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 modern hotel room with a bed, sofa, desk, and a round orange table.
A modern reception desk with a wooden panel backdrop, a crescent-shaped light fixture, and a refrigerator stocked with beverages.
A modern building with a blue-lit facade, a snow-covered ground, and a visible snow-clearing vehicle.

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 narrow hallway with a microwave and trash bin on the left, leading to a door with a sign.
A living room with a fireplace, a flat-screen TV, and patterned sofas.
A reception area with a stone wall, a reception desk, and a seating area with patterned chairs.

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 modern bistro bar with a wooden counter, a refrigerated display, and a menu board.
A modern bar area with a wooden counter, bar stools, and a menu board above.
A circular outdoor seating area with a fire pit, surrounded by wicker chairs and a brick wall.
A Courtyard by Marriott hotel with a modern facade, multiple floors, and a parking lot in front.

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 lobby with a central seating area featuring patterned chairs, a round table, and a chandelier.
A hotel room with a bed, a sofa, a small ottoman, a nightstand with a lamp, and a wall-mounted picture.
A modern hotel with a covered entrance, large windows, and a sign indicating it is a Home2 Suites location.

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 swimming pool with lounge chairs and a blue wall.
A hotel room with a kitchenette, a flat-screen TV, a sofa, and a large window.

Hampton Inn & Suites Richmond, IN

Hampton Inn & Suites Richmond, IN
Richmond

10/10 Exceptional

United States
Anonymous traveler
Hampton Inn & Suites Richmond, IN
A lobby with a stone wall, a coffee station, two green sofas, and a white table.
A corner market with refrigerated and non-refrigerated food sections, a vending machine, and a wall with informational posters.
A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.
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 hotel room with a large bathtub, a double bed, a desk, and a chair.
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.
A hotel with a red roof, beige walls, and a central entrance with a sign.

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 television on a wooden dresser in a hotel room.
A compact room with a microwave on a small black appliance, a blue ironing board, a lamp, and a wall-mounted ironing board.
A bathroom with a toilet, a bathtub, and a shower curtain.

Hoosier Inn

Hoosier Inn
Portland

10/10 Exceptional

United States
Rita
Hoosier Inn
A reception desk with a "Welcome to Richmond" sign, a plant, and a snack bar in the background.
A modern indoor pool area with lounge chairs, a pool table, and a reception desk.
A mural with 'Rose City' prominently displayed, surrounded by various illustrated landmarks and attractions.
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 breakfast buffet area with a sign that reads "HAPPY BREAKFAST STARTS HERE."
A Hampton Inn & Suites with a modern facade, large entrance, and well-lit exterior.
A modern indoor swimming pool with clear blue water, surrounded by lounge chairs and a poolside bar.
A hotel room with a kitchenette, a desk, a sofa, and a large window.

Hampton Inn & Suites Muncie

Hampton Inn & Suites Muncie
Muncie

10/10 Exceptional

United States
Keturah
Hampton Inn & Suites Muncie
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 Fairfield Inn Marriott hotel with a modern facade, a well-lit entrance, and a parking area with marked spaces.
A vending machine area with snacks and beverages.

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 reception area with two white reception desks, a blue and white geometric wall art, and a wooden accent wall.
A snack bar with shelves of chips and snacks, a refrigerated section with drinks and food, and a display of bottled water.
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
A hotel room with two beds, a TV, a dresser, a bench, and a mirror.
A hotel room with a bed, a desk, a chair, a lamp, and a painting on the wall.
Bathroom
A motel with a parking lot, a red birdbath, and a tree with green leaves.

The Golden Inn

The Golden Inn
New Paris

10/10 Exceptional

United States
donna
The Golden Inn

Frequently Asked Questions

How much does a hotel room cost in Winchester?

You can choose a great hotel in Winchester from CNY361 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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