Hotels in Winchester

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Top 5 hotels in Winchester at a glance

Randolph Inn and Suites — 2.5-star hotel in Winchester. Guest rating: 9.0/10 — Wonderful.
Holiday Inn Express & Suites Portland by IHG — 2.5-star hotel in Portland. Guest rating: 9.2/10 — Wonderful.
Baymont by Wyndham Richmond I-70 — 2.5-star hotel in Richmond. Guest rating: 8.6/10 — Excellent.
Comfort Suites Richmond East — 2.5-star hotel in Richmond. Guest rating: 9.4/10 — Exceptional.
Quality Inn Greenville North — 2.5-star hotel in Greenville. Guest rating: 8.2/10 — Very Good.

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.

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

Winchester

$108

$121 total

includes taxes & fees

Aug 28 - Aug 29

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

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

An indoor swimming pool with lounge chairs and exercise equipment.

A modern hotel lobby with a seating area, a reception desk, and artwork on the walls.

Holiday Inn Express & Suites Portland by IHG

Portland

$103

$115 total

includes taxes & fees

Sep 27 - Sep 28

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.

Baymont by Wyndham Richmond I-70

Richmond

$79

$89 total

includes taxes & fees

Sep 13 - Sep 14

A covered outdoor seating area with a fire pit, sofas, and a pergola.

A modern building with a blue-lit facade, a snow-covered ground, and a visible snow-clearing vehicle.

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

Richmond

$107

$122 total

includes taxes & fees

Aug 30 - Aug 31

A hotel room with a large bathtub, a double bed, a desk, and a chair.

A gym with multiple rows of dumbbells on racks, a blue trash bin, and a red chair.

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.

Quality Inn Greenville North

Greenville

$102

$116 total

includes taxes & fees

Sep 20 - Sep 21

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

Courtyard Muncie at Horizon Convention Center

Muncie

$110

$123 total

includes taxes & fees

Sep 3 - Sep 4

A spacious dining area with multiple tables and chairs, a kitchen counter with appliances, and a painting on the 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.

Surestay By Best Western Greenville

Greenville

$92

$104 total

includes taxes & fees

Sep 2 - Sep 3

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

A compact room with a microwave on a small black appliance, a blue ironing board, a lamp, and a wall-mounted ironing board.

Hoosier Inn

Portland

$81

$91 total

includes taxes & fees

Aug 31 - Sep 1

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

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.

A large indoor swimming pool with multiple seating areas and a clear view of the outdoors through large windows.

Motel 6 Richmond, IN

Richmond

$61

$69 total

includes taxes & fees

Aug 30 - Aug 31

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

A motel with a Super 8 sign, large windows, a covered parking area, and a well-maintained lawn.

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

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

Super 8 by Wyndham Centerville-Richmond

Centerville

$57

$64 total

includes taxes & fees

Sep 13 - Sep 14

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

A suburban street with a house, a 'No Parking' sign, and a utility pole.

A hotel room with a bed, a desk, a chair, a lamp, and a painting on the wall.

The Golden Inn

New Paris

$79

$89 total

includes taxes & fees

Aug 31 - Sep 1

A modern hotel lobby with green seating, a reception desk, and a dining area in the background.

A modern hotel room with a large bed, a desk, a chair, and a small table.

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

An indoor swimming pool with clear pool rules posted, a lifeguard chair, and a bench.

Holiday Inn Express Hotel & Suites Greenville by IHG

Greenville

$112

$127 total

includes taxes & fees

Sep 27 - Sep 28

A reception desk with a "Welcome to Richmond" sign, a plant, and a snack bar in the background.

A modern dining area with a large table and chairs, large windows with a view of trees, and a neon sign on the wall.

A mural with 'Rose City' prominently displayed, surrounded by various illustrated landmarks and attractions.

An outdoor patio with a fire feature, seating, and a view into the interior.

Best Western Plus Richmond Indiana I-70

Richmond

$101

$113 total

includes taxes & fees

Sep 10 - Sep 11

A building with a stone facade, a 'Lobby' sign, and a glass entrance.

A Red Roof Inn lobby with a stone fireplace, leather chairs, a flat-screen TV, and a sign indicating free Wi-Fi in all rooms.

A motel with multiple rooms, a fenced parking area, and a grassy front lawn.

A hotel lobby with a stone fireplace, leather chairs, a large window, and an exit sign.

Red Roof Inn Richmond, IN

Richmond

$49

$55 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

A corner market with refrigerated and non-refrigerated food sections, a vending machine, and a wall with informational posters.

Fairfield Inn by Marriott Richmond

New Paris

$114

$129 total

includes taxes & fees

Sep 6 - Sep 7

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

Richmond

$122

$137 total

includes taxes & fees

Sep 6 - Sep 7

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

Richmond

$122

$137 total

includes taxes & fees

Sep 6 - Sep 7

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 restaurant with a blue and white color scheme, featuring a 'Daybreak Breakfast' sign, a kitchen area with a microwave and coffee machine, and several tables and chairs.

Days Inn by Wyndham Muncie -Ball State University

Muncie

$60

$67 total

includes taxes & fees

Sep 6 - Sep 7

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.

A two-story building with a brick facade, a covered entrance, and a clear sky.

Motel 6 Portland, IN

Portland

$72

$81 total

includes taxes & fees

Aug 31 - Sep 1

A reception desk with a clock, a sign, and a wooden cabinet.

A compact room with a television on a wooden cabinet, a microwave, a coffee maker, and a chair.

A hotel room with a bed, a desk, a television, and a window with curtains.

A room with a closed door, two windows, a blue sofa, a wooden coffee table, a globe, and a mirror.

Richmond Inn & Suites

Richmond

$59

$72 total

includes taxes & fees

Aug 28 - Aug 29

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Go beyond your typical stay in Winchester

Pet friendly

Pool

Family friendly

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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Check out reviews of Winchester hotels guests love

Motel 6 Richmond, IN

10/10 Excellent

"This hotel was great!!"

Best Western Plus Richmond Indiana I-70

10/10 Excellent

"Very friendly staff.and clean rooms. I found it easy to relax there. Buffet breakfast included scrambled eggs, which I appreciated. The extra touch was the outdoor space for morning and it looked like the evening with patio lights and possibly a gas fireplace; not sure, as it was covered, but it was a very nice patio. Nice stay overall!"

Comfort Suites Richmond East

10/10 Excellent

"Just a one night stay on our drive across the country- but very happy with our stay. Room was clean, beds were comfortable and plenty of restaurants nearby for a quick meal. Parking was easy. Would recommend."

Hampton Inn & Suites Muncie

10/10 Excellent

"Very clean an well maintained."

Quality Inn and Conference Center

10/10 Excellent

"Check in great. Handicap accessibility very questionable. Cleanliness I could live with for a one night stay. TV totally sucked. Breakfast does not even qualify as such. Bathtub is a slippery lawsuit waiting to happen Nice service people. But. Won’t be back."

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.

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