Winchester Holiday Rentals, Indiana: Private House Rentals

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Our top choices for Winchester hotels

A golf course with a pond, trees, and a clear sky.

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

A living room with a fireplace, a television mounted above it, and a carpeted floor.

A kitchen with a granite countertop, a stainless steel sink, wooden cabinets, a coffee maker, and a trash can.

1. Randolph Inn and Suites

Winchester

Courtney

฿3,253

฿3,644 total

includes taxes & fees

27 Sept - 28 Sept

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.

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

A living room with a fireplace, a flat-screen TV, and patterned sofas.

2. Baymont by Wyndham Richmond I-70

Richmond

Gerard

฿2,530

฿2,834 total

includes taxes & fees

27 Sept - 28 Sept

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 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.

3. Fairfield Inn by Marriott Richmond

New Paris

Cody

฿3,812

฿4,317 total

includes taxes & fees

4 Oct - 5 Oct

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

A Comfort Suites hotel with a modern design, featuring a large entrance and multiple parking spaces.

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

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

4. Comfort Suites Richmond East

Richmond

Audrey

฿3,679

฿4,187 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel lobby with seating areas, tables, and artwork on the walls.

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.

A snack display area with various packaged snacks and a refrigerated section with frozen goods.

5. Hampton Inn & Suites Richmond, IN

Richmond

Tom

฿4,089

฿4,580 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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.

6. Best Western Plus Richmond Indiana I-70

Richmond

Kevin

฿3,387

฿3,793 total

includes taxes & fees

4 Oct - 5 Oct

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 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.

7. Holiday Inn Express & Suites Portland by IHG

Portland

Jeff

฿3,849

฿4,311 total

includes taxes & fees

25 Oct - 26 Oct

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 seating area, a TV, and a reception desk.

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.

8. Home2 Suites by Hilton Richmond

Richmond

Gerritt

฿4,089

฿4,580 total

includes taxes & fees

4 Oct - 5 Oct

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.

9. Quality Inn Greenville North

Greenville

Kayla

฿3,467

฿3,926 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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.

10. Days Inn by Wyndham Muncie -Ball State University

Muncie

bruce

฿2,048

฿2,294 total

includes taxes & fees

25 Oct - 26 Oct

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 two beds, a desk, a TV, and a dresser.

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.

11. Super 8 by Wyndham Centerville-Richmond

Centerville

Carolyn

฿1,805

฿2,022 total

includes taxes & fees

4 Oct - 5 Oct

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.

A Courtyard by Marriott hotel with a modern facade, multiple floors, and a parking lot in front.

A modern bar area with a wooden counter, bar stools, and a menu board above.

12. Courtyard Muncie at Horizon Convention Center

Muncie

Krista

฿3,665

฿4,105 total

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with a stone accent wall, a black countertop, and a wooden dining area with chairs.

A vending machine area with snacks and beverages.

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.

13. Fairfield Inn by Marriott Muncie

Muncie

Clifford

฿3,735

฿4,184 total

includes taxes & fees

4 Oct - 5 Oct

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

A modern hotel room with two beds, a desk with a computer, a chair, and a television.

A hotel reception desk with a modern design, featuring a wooden panel wall, a digital display, and a reception counter.

An indoor swimming pool with yellow chairs and tables, a blue ceiling, and a sign reading "POOLSIDE IS MY VIBE".

14. Home2 Suites By Hilton Muncie

Muncie

Katherine

฿4,089

฿4,580 total

includes taxes & fees

4 Oct - 5 Oct

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.

15. Hampton Inn & Suites Muncie

Muncie

Lisa

฿3,541

฿3,965 total

includes taxes & fees

4 Oct - 5 Oct

Vending machines for Pepsi and an ice dispenser in a hotel corridor.

A reception desk with a digital screen displaying 'Free Wi-Fi All Rooms' and a security camera above the door.

A hotel room with a bed, a desk with a chair, a television, and a door.

A laundry room with a front-loading washing machine and a wall-mounted dryer. There are two illuminated wall sconces above the machines. A sign indicating laundry room hours is visible on the wall.

16. Red Roof Inn Richmond, IN

Richmond

Jeff

฿1,818

฿2,037 total

includes taxes & fees

8 Oct - 9 Oct

A hotel hallway with a sofa, a lamp, a TV, and a view into a bedroom.

A swimming pool with clear lane markings, a lifeguard chair, and a window with a view of trees.

A Holiday Inn Express hotel with a covered entrance, brick facade, and multiple windows.

A snack bar with shelves of chips and snacks, a refrigerated section with drinks and food, and a display of bottled water.

17. Holiday Inn Express Richmond by IHG

Richmond

Pengxiang

฿3,849

฿4,311 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a desk, a chair, a TV, a bathroom with a sink and mirror, and a view of the outside.

A modern interior with a sectional sofa, round coffee table, and wicker chairs.

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

18. Best Western Muncie

Muncie

Kalea

฿2,959

฿3,314 total

includes taxes & fees

4 Oct - 5 Oct

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.

19. The Golden Inn

New Paris

David

฿2,644

฿2,995 total

includes taxes & fees

28 Sept - 29 Sept

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

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

A gym with exercise equipment, a potted plant, and a window with blinds.

Two vending machines with snack options and a drink dispenser.

20. Motel 6 Portland, IN

Portland

Tommy

฿2,409

฿2,698 total

includes taxes & fees

27 Sept - 28 Sept

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Stay near popular Winchester attractions

Winchester Speedway

7.8/10 (26 reviews)

Experience heart-pounding action at the world's fastest half-mile paved track with its legendary steep, high-banked turns. Arrive early to secure prime seating for the electrifying races.

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Randolph County Courthouse

9.0/10 (2 reviews)

After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester.

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Winchester Golf Club

7.2/10 (13 reviews)

This scenic golf club features three distinct 9-hole courses with unique challenges and mature landscaping. Enjoy the welcoming clubhouse after testing your skills on the rolling Beeson, Pony, or Willow courses.

See properties

Top Winchester Hotel Reviews

Comfort Suites Richmond East

10/10 Excellent

"everything about this hotel was perfect. everything was clean breakfast was exceptional. would definitely stay here again."

Hampton Inn & Suites Richmond, IN

10/10 Excellent

"Clean and comfortable room with excellent breakfast."

Muncie Place Hotel & Suites

8/10 Good

"Nice Hotel"

Comfort Inn & Suites Muncie Near University

8/10 Good

"Very nice room. My block out curtains needed fixing. Told one of the men upfront about it. Didn't fix it. Gave him permission to enter the room. Privacy from windows wasn't good. Can see into the room at night. Coffee was terrible. Overall not really bad. Just little things not like "home"."

Best Western Plus Richmond Indiana I-70

8/10 Good

"The property was conveniently located near I-70. Several restaurants nearby. Room was clean,and bed was comfortable. The breakfast was the standard fare. Eggs, sausage, potatoes, and waffles with a couple other foods, yogurt, muffins, etc."

Home2 Suites By Hilton Muncie

10/10 Excellent

"This hotel is the place to stay in Muncie. I love the laminate floors, seems so much cleaner. The people who work here are super friendly and helpful. The free breakfast is decent. The bed was comfortable. There is a patio out front where we were able to sit outside with a small fire pit and enjoy the weather. The area around the hotel is quiet and nice. I definitely recommend to stay here when in Muncie."

Randolph Inn and Suites

10/10 Excellent

"This was a great choice for housing my family. Three suites for 8 people. Owners were super friendly and helpful!"

Fairfield Inn by Marriott Muncie

10/10 Excellent

"Clean room. Friendly staff"

Holiday Inn Express Hotel & Suites Greenville by IHG

10/10 Excellent

"We stayed here for THE WORLD 100 Eldora Speedway race and WOW THE staff were so nice! The property was so clean! The breakfast had so much variety! They have all updated coffee machines that are automatic and a pancake maker! Lol The bedding was clean and I am strict about that while staying in a hotel. The pillows were seriously the most comfortable pillows! We will definitely be staying there for future visits"

More cheap stays in Winchester

Quality Inn and Conference Center

5501 National Rd E Richmond IN

฿1,849

฿2,071 total

18 Oct - 19 Oct

includes taxes & fees

6.6/10 (1,000 reviews)

Motel 6 Richmond, IN

6030 National Road East Richmond IN

฿1,960

฿2,195 total

1 Oct - 2 Oct

includes taxes & fees

Days Inn by Wyndham Muncie -Ball State University

3509 N Everbrook Ln Muncie IN

฿2,048

฿2,294 total

25 Oct - 26 Oct

includes taxes & fees

6.8/10 (971 reviews)

Baymont by Wyndham Richmond I-70

912 Mendleson Dr Richmond IN

฿2,530

฿2,834 total

27 Sept - 28 Sept

includes taxes & fees

Best Western Plus Richmond Indiana I-70

533 W Eaton Pike Richmond IN

฿3,387

฿3,793 total

4 Oct - 5 Oct

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Comfort Suites Richmond East

421 Commerce Road Richmond IN

฿3,679

฿4,187 total

25 Oct - 26 Oct

includes taxes & fees

9.4/10 Exceptional! (858 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?

Based on our traveller data, Randolph Inn and Suites is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Two other choices for your visit to the area are Days Inn by Wyndham Muncie -Ball State University and Motel 6 Richmond, IN. See all available top hotels, or vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, you'll find most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it may still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What's it like staying in Winchester?

Visitors can enjoy all that Winchester has to offer, including its golf courses. In Winchester, there are 2 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

A couple of favourite places to visit are Winchester Speedway and Winchester Golf Club. You'll also find Levi Coffin House and Prairie Creek Reservoir and Campground in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the seasonal weather in Winchester?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. Average annual precipitation for Winchester is 1190 mm.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, IN from ฿2,022

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Randolph Inn and Suites

2. Baymont by Wyndham Richmond I-70

3. Fairfield Inn by Marriott Richmond

4. Comfort Suites Richmond East

5. Hampton Inn & Suites Richmond, IN

6. Best Western Plus Richmond Indiana I-70

7. Holiday Inn Express & Suites Portland by IHG

8. Home2 Suites by Hilton Richmond

9. Quality Inn Greenville North

10. Days Inn by Wyndham Muncie -Ball State University

11. Super 8 by Wyndham Centerville-Richmond

12. Courtyard Muncie at Horizon Convention Center

13. Fairfield Inn by Marriott Muncie

14. Home2 Suites By Hilton Muncie

15. Hampton Inn & Suites Muncie

16. Red Roof Inn Richmond, IN

17. Holiday Inn Express Richmond by IHG

18. Best Western Muncie

19. The Golden Inn

20. Motel 6 Portland, IN

Stay near popular Winchester attractions

Winchester Speedway

Randolph County Courthouse

Winchester Golf Club

Top Winchester Hotel Reviews

Comfort Suites Richmond East

Hampton Inn & Suites Richmond, IN

Muncie Place Hotel & Suites

Comfort Inn & Suites Muncie Near University

Best Western Plus Richmond Indiana I-70

Home2 Suites By Hilton Muncie

Randolph Inn and Suites

Fairfield Inn by Marriott Muncie

Holiday Inn Express Hotel & Suites Greenville by IHG

More cheap stays in Winchester

Quality Inn and Conference Center

Motel 6 Richmond, IN

Days Inn by Wyndham Muncie -Ball State University

Baymont by Wyndham Richmond I-70

Best Western Plus Richmond Indiana I-70

Comfort Suites Richmond East

Frequently asked questions

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