Hotels in Winchester

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Where to stay in Winchester?

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.

An indoor swimming pool with clear water, a white chair, and windows allowing natural light.

A kitchenette with a refrigerator, coffee machine, and a microwave. There is a sign indicating a meeting room.

1. Randolph Inn and Suites

Winchester

$108

$121 total

includes taxes & fees

Oct 14 - Oct 15

A spacious indoor area with multiple seating arrangements, including tables and chairs, and large windows offering views of the outdoors.

A reception area with two reception desks, a central counter, and a sign for Holiday Inn Express & Suites.

A modern hotel room with a desk, chairs, a computer, and a couch.

A Holiday Inn Express hotel with a covered entrance, brick facade, and a clear blue sky.

2. Holiday Inn Express & Suites Portland by IHG

Portland

$110

$123 total

includes taxes & fees

Oct 18 - Oct 19

A hotel room with a large bed, a desk with a computer, a chair, and a TV.

An indoor swimming pool with clear lane markings, a lifeguard chair, and a door in the background.

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.

3. Baymont by Wyndham Richmond I-70

Richmond

$77

$87 total

includes taxes & fees

Oct 18 - Oct 19

A hotel room with two beds, a desk with a TV, a dresser, and a window with curtains.

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.

A reception desk with a wooden counter, a clock, and a no-smoking sign.

4. Motel 6 Portland, IN

Portland

$63

$71 total

includes taxes & fees

Oct 14 - Oct 15

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 television on a wooden dresser in a hotel room.

A bathroom with a toilet, a bathtub, and a shower curtain.

5. Hoosier Inn

Portland

$81

$91 total

includes taxes & fees

Oct 18 - Oct 19

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.

6. Surestay By Best Western Greenville

Greenville

$92

$104 total

includes taxes & fees

Oct 19 - Oct 20

A hotel entrance with a stone facade, a covered entrance, and a ramp for accessibility.

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.

A coffee station with a coffee machine, disposable cups, and coffee creamer bottles.

7. Red Roof Inn Richmond, IN

Richmond

$48

$54 total

includes taxes & fees

Oct 25 - Oct 26

A hotel reception area with a counter, a refrigerator, and a coffee machine.

A room with a patterned armchair, a glass-top desk with a vase of flowers, and a view through a window with curtains.

A kitchen with a stainless steel refrigerator, a double sink, and a microwave.

A hotel hallway with a carpeted floor, wooden handrails, and an exit sign on the ceiling.

8. Empire Inn & Suites Muncie -Ball State University

Muncie

$63

$71 total

includes taxes & fees

Nov 1 - Nov 2

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

Economy

$108

$326 total

includes taxes & fees

Oct 14 - Oct 15

A hotel room with three beds, a desk, and a chair. There are paintings on the walls and a window with curtains.

A bathroom with a white sink, green countertop, and a mirror reflecting a door and a bathtub.

A hotel room with a large mirror, a coffee machine, a clock, and a door with a curtain.

A hotel room with two beds, a desk, a TV, and a dresser.

10. Super 8 by Wyndham Centerville-Richmond

Centerville

$54

$60 total

includes taxes & fees

Oct 25 - Oct 26

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 large indoor swimming pool with wooden walls and arched windows.

A hotel with a red roof, beige walls, and a central entrance with a sign.

11. Quality Inn Greenville North

Greenville

$97

$109 total

includes taxes & fees

Nov 2 - Nov 3

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 hotel room with a large bed, bedside tables, a chair, and a desk.

A modern office space with a reception area, multiple workstations, and comfortable seating.

12. Holiday Inn Express Hotel & Suites Greenville by IHG

Greenville

$110

$125 total

includes taxes & fees

Oct 25 - Oct 26

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 hotel room with two beds, a desk, a chair, a TV, and a large window with curtains.

A circular outdoor seating area with a fire pit, surrounded by wicker chairs and a brick wall.

13. Courtyard Muncie at Horizon Convention Center

Muncie

$110

$123 total

includes taxes & fees

Oct 19 - Oct 20

An outdoor patio with grey sofas, a circular stone fire pit, and a pergola with string lights.

A modern reception desk with a wooden panel backdrop, a crescent-shaped light fixture, and a refrigerator stocked with beverages.

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 hotel room with a bed, sofa, desk, and a round orange table.

14. Comfort Suites Richmond East

Richmond

$115

$130 total

includes taxes & fees

Oct 25 - Oct 26

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.

A motel with a parking lot, a red birdbath, and a tree with green leaves.

15. The Golden Inn

New Paris

$75

$85 total

includes taxes & fees

Oct 16 - Oct 17

A hotel room with a large bed, wooden headboard, bedside tables, and wall-mounted artwork depicting autumn leaves and a sunset over water.

A staircase with a patterned carpet leading to a landing. A modern pendant light hangs above the staircase.

A modern hotel lobby with a staircase, a large wall-mounted TV, and two potted plants.

A modern lobby with a staircase, a seating area, a fireplace, vending machines, and a water dispenser.

16. Days Inn by Wyndham Muncie -Ball State University

Muncie

$59

$66 total

includes taxes & fees

Oct 18 - Oct 19

A spacious lobby with a wooden staircase, a chandelier, and a reception desk.

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.

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.

17. Motel 6 Richmond, IN

Richmond

$59

$66 total

includes taxes & fees

Oct 26 - Oct 27

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.

18. Best Western Plus Richmond Indiana I-70

Richmond

$93

$105 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor seating area with fire pits and modern furniture, overlooking a street with buildings and a sunset view.

A modern hotel with a prominent "HOME 2" sign, multiple floors, and a well-lit entrance area.

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.

19. Home2 Suites By Hilton Muncie

Muncie

$127

$142 total

includes taxes & fees

Oct 25 - Oct 26

A hotel entrance with a covered parking area, numbered 3601, and a clear sky.

A reception area with a tiled counter, a black leather sofa, and a tiled floor.

A workspace with a computer monitor on a stand, a keyboard, a mouse, and a leather chair.

A hotel room with two beds, a desk, a chair, a TV, and a large window.

20. Super 8 by Wyndham Muncie/Ball St. College Area

Muncie

$60

$67 total

includes taxes & fees

Nov 1 - Nov 2

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Go beyond your typical stay in Winchester

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

Randolph Inn and Suites

Winchester

10/10 Exceptional

Tracy

Holiday Inn Express & Suites Portland by IHG

Portland

10/10 Exceptional

Anonymous traveler

Baymont by Wyndham Richmond I-70

Richmond

10/10 Exceptional

jason

Hoosier Inn

Portland

10/10 Exceptional

Rita

Comfort Suites Richmond East

Richmond

10/10 Exceptional

Kimberly

Courtyard Muncie at Horizon Convention Center

Muncie

10/10 Exceptional

Ron

The Golden Inn

New Paris

10/10 Exceptional

donna

Quality Inn Greenville North

Greenville

10/10 Exceptional

Kyleen

Motel 6 Portland, IN

Portland

10/10 Exceptional

James

A lobby with a stone wall, a coffee station, two green sofas, and a white table.

A Fairfield Inn & Suites hotel with a covered parking area and a landscaped entrance.

A hotel reception area with a reception desk, a corner market, and a decorative wall piece.

A hotel room with two beds, a desk, a chair, a small table, and a window with curtains.

Fairfield Inn by Marriott Richmond

New Paris

10/10 Exceptional

Marie

An outdoor patio with yellow chairs and tables, a wooden ceiling with lights, and a view of buildings in the background.

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 central seating area featuring patterned chairs, a round table, and a chandelier.

A modern hotel lobby with a seating area, a TV, and a reception desk.

Home2 Suites by Hilton Richmond

Richmond

10/10 Exceptional

Chuck

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 two beds, a TV, a wooden dresser, and a door leading to another room.

A swimming pool with lounge chairs and a blue wall.

Hampton Inn & Suites Richmond, IN

Richmond

10/10 Exceptional

I stayed here twice within a 9 day period, driving from PA to MO and then from MO to PA. Great hotel - very clean, helpful staff, great breakfast, close to I70, convenient to restaurants, movie theater, pharmacy, etc. When I checked in for the second stay they gave me a free upgrade to a jacuzzi suite. Just what I needed after a long day of driving! As a woman traveling alone, I felt this hotel was in a safe neighborhood and would highly recommend it.

Anonymous traveler

Best Western Plus Richmond Indiana I-70

Richmond

10/10 Exceptional

Amy

Red Roof Inn Richmond, IN

Richmond

10/10 Exceptional

Clayton

A breakfast buffet area with a sign that reads "HAPPY BREAKFAST STARTS HERE."

A hotel room with a kitchenette, a desk, a sofa, and a large window.

A hotel room with two beds, a desk with a TV, a mirror, a chair, and a microwave.

A Hampton Inn & Suites with a modern facade, large entrance, and well-lit exterior.

Hampton Inn & Suites Muncie

Muncie

10/10 Exceptional

The lobby was inviting and clean. The front desk staff, Riley, was friendly and let us know about many things to do around the area. We swam in the salt water pool and had free breakfast the next morning. Audrey checked us out in the morning. She did a great job also. Our experience was extremely enjoyable. There were even surrounding hotels that we could have chosen, but this one came highly recommended. My family and I will be staying here the next time we come to town and visit family!

Keturah

Super 8 by Wyndham Muncie/Ball St. College Area

Muncie

10/10 Exceptional

Solar

Frequently Asked Questions

What accommodations do travelers like in Winchester?

Guests like Randolph Inn and Suites.

Can I book a refundable accommodation in Winchester?

If you want the flexibility to change your plans to Winchester, most hotels provide refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Winchester if I'm looking for an affordable accommodation?

An inexpensive option worth considering is Randolph Inn and Suites.

What will the weather in Winchester be like during my vacation?

July and August are typically the warmest months in Winchester when the average temp is 70°F. January and February are the coldest months when the average temperature is 33°F. May and June are the months with the most rain.

Why should I book my Winchester accommodation with Hotels.com?

There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.