Winchester Holiday Rentals, Indiana: Private House Rentals

A historic building with a clock tower, a statue, and well-maintained gardens.

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Our top choices for Winchester hotels

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

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

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

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

Sheri

Rp1.740.172

Rp1.948.921 total

includes taxes & fees

17 Oct - 18 Oct

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

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

A gym with cardio machines, a pool, and large windows offering a view of the outdoors.

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

2. Holiday Inn Express & Suites Portland by IHG

Portland

Mary

Rp1.847.614

Rp2.069.328 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

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

Richmond

Gerard

Rp1.353.467

Rp1.515.847 total

includes taxes & fees

25 Oct - 26 Oct

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.

4. Comfort Suites Richmond East

Richmond

April

Rp1.961.453

Rp2.232.634 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a desk, a chair, two bedside tables with lamps, and a window with curtains.

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.

5. Surestay By Best Western Greenville

Greenville

don

Rp1.627.335

Rp1.842.957 total

includes taxes & fees

17 Oct - 18 Oct

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

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

6. Courtyard Muncie at Horizon Convention Center

Muncie

Jennifer

Rp1.966.902

Rp2.202.930 total

includes taxes & fees

25 Oct - 26 Oct

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

7. Quality Inn Greenville North

Greenville

Janell

Rp1.727.609

Rp1.956.517 total

includes taxes & fees

16 Nov - 17 Nov

A modern self-service coffee station with multiple coffee machines, a display of coffee beans, and a variety of condiments.

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

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.

8. Home2 Suites By Hilton Muncie

Muncie

George

Rp2.119.375

Rp2.373.700 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

9. Home2 Suites by Hilton Richmond

Richmond

Colby

Rp2.187.389

Rp2.449.876 total

includes taxes & fees

25 Oct - 26 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 dining area with a large table and chairs, large windows with a view of trees, and a neon sign on the wall.

A modern indoor pool area with lounge chairs, a pool table, and a reception desk.

10. Best Western Plus Richmond Indiana I-70

Richmond

Kevin

Rp1.673.751

Rp1.874.602 total

includes taxes & fees

14 Nov - 15 Nov

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.

11. Hampton Inn & Suites Richmond, IN

Richmond

Josh

Rp2.191.844

Rp2.454.865 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

A breakfast area with a counter, food display, and a sign for Express Start Breakfast.

12. Holiday Inn Express Hotel & Suites Greenville by IHG

Greenville

Kathryn

Rp1.969.330

Rp2.230.266 total

includes taxes & fees

25 Oct - 26 Oct

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

13. Fairfield Inn by Marriott Richmond

New Paris

John

Rp2.039.152

Rp2.309.339 total

includes taxes & fees

25 Oct - 26 Oct

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 television on a wooden dresser in a hotel room.

14. Hoosier Inn

Portland

Larry E

Rp1.450.143

Rp1.624.160 total

includes taxes & fees

14 Nov - 15 Nov

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 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.

15. Super 8 by Wyndham Centerville-Richmond

Centerville

Carolyn

Rp965.688

Rp1.081.571 total

includes taxes & fees

25 Oct - 26 Oct

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

Two vending machines with snack options and a drink dispenser.

16. Motel 6 Portland, IN

Portland

Tommy

Rp1.127.527

Rp1.262.830 total

includes taxes & fees

22 Oct - 23 Oct

A vending area with Coca-Cola and Pepsi machines.

An indoor swimming pool with a brick wall and wooden ceiling, surrounded by lounge chairs and a covered seating area.

A hotel room with a large bed, bedside lamps, a desk, an office chair, a window with curtains, and an air conditioning unit.

17. Best Western Muncie

Muncie

Kalea

Rp1.600.787

Rp1.792.882 total

includes taxes & fees

1 Nov - 2 Nov

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 breakfast bar with various food items and kitchen appliances.

A hotel room with a blue sofa, a wooden coffee table, a small side table, and a bed with a brown blanket.

18. Comfort Inn & Suites Muncie Near University

Muncie

Christopher

Rp1.707.518

Rp1.912.419 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

19. Red Roof Inn Richmond, IN

Richmond

Jeff

Rp844.878

Rp946.263 total

includes taxes & fees

22 Oct - 23 Oct

A hotel room with a large bed, a smaller bed, a nightstand, a lamp, and a window with curtains.

A reception desk with a modern design, featuring a wavy pattern on the wall behind it and a blue LED light strip along the base.

A breakfast area with a counter, coffee machines, and seating.

A hotel with a sign reading "Quality Inn & Suites" and a modern building with multiple floors.

20. Quality Inn and Conference Center

Richmond

Dale

Rp1.077.177

Rp1.206.438 total

includes taxes & fees

8 Nov - 9 Nov

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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.

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Learn more about Winchester

In the heart of small-town America, Winchester's Historic Shopping & Dining District invites visitors to explore local heritage while savouring hometown flavours. Racing enthusiasts can catch high-octane action at Winchester Speedway, while golfers enjoy peaceful rounds at the well-maintained Winchester Golf Club.

See all hotels in Winchester

Top Winchester Hotel Reviews

Best Western Plus Richmond Indiana I-70

10/10 Excellent

"🙂"

Hampton Inn & Suites Muncie

10/10 Excellent

"This hotel felt fresh and recently renovated. If only we had been prepared to enjoy the pool and exercise room, which were across the hall from our room - we would have had them to ourselves! I would have loved to use the Peloton bike and take a swim. (For an additional $20, we could have had a Peloton bike in our room!) The breakfast, as is typical of Hampton Inn, wasn't great, but it was pretty good, and the staffer working the breakfast area was welcoming and friendly. This hotel was in great condition and renewed our hope in Hampton Inn as a national chain after a bad experience this summer elsewhere."

Randolph Inn and Suites

10/10 Excellent

"Loved the food"

Fairfield Inn by Marriott Muncie

10/10 Excellent

"Rooms were clean, comfortable and safe. Staff very friendly, helpful and professional. Breakfast great selection, hot and taste good. Good location and price. Very pleased with our choice of hotel."

Hampton Inn & Suites Richmond, IN

10/10 Excellent

"Great place to stay. Bed and room was great.breakfast was good. Close to some of the State Parks."

Home2 Suites By Hilton Muncie

8/10 Good

"Room was as advertised, clean and as comfortable as expected at this price point. The breakfast was meh."

Comfort Inn & Suites Muncie Near University

8/10 Good

"Blackout curtain was broken and the electrical outlet in the bathroom kept shutting off."

More cheap stays in Winchester

Motel 6 Richmond, IN

6030 National Road East Richmond IN

Rp987.666

Rp1.106.057 total

31 Oct - 1 Nov

includes taxes & fees

Days Inn by Wyndham Muncie -Ball State University

3509 N Everbrook Ln Muncie IN

Rp1.050.011

Rp1.176.012 total

26 Oct - 27 Oct

includes taxes & fees

Quality Inn and Conference Center

5501 National Rd E Richmond IN

Rp1.077.177

Rp1.206.438 total

8 Nov - 9 Nov

includes taxes & fees

Baymont by Wyndham Richmond I-70

912 Mendleson Dr Richmond IN

Rp1.353.467

Rp1.515.847 total

25 Oct - 26 Oct

includes taxes & fees

Best Western Plus Richmond Indiana I-70

533 W Eaton Pike Richmond IN

Rp1.673.751

Rp1.874.602 total

14 Nov - 15 Nov

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Comfort Suites Richmond East

421 Commerce Road Richmond IN

Rp1.961.453

Rp2.232.634 total

25 Oct - 26 Oct

includes taxes & fees

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 Rp1.106.057

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. Holiday Inn Express & Suites Portland by IHG

3. Baymont by Wyndham Richmond I-70

4. Comfort Suites Richmond East

5. Surestay By Best Western Greenville

6. Courtyard Muncie at Horizon Convention Center

7. Quality Inn Greenville North

8. Home2 Suites By Hilton Muncie

9. Home2 Suites by Hilton Richmond

10. Best Western Plus Richmond Indiana I-70

11. Hampton Inn & Suites Richmond, IN

12. Holiday Inn Express Hotel & Suites Greenville by IHG

13. Fairfield Inn by Marriott Richmond

14. Hoosier Inn

15. Super 8 by Wyndham Centerville-Richmond

16. Motel 6 Portland, IN

17. Best Western Muncie

18. Comfort Inn & Suites Muncie Near University

19. Red Roof Inn Richmond, IN

20. Quality Inn and Conference Center

Stay near popular Winchester attractions

Winchester Speedway

Randolph County Courthouse

Winchester Golf Club

Learn more about Winchester

Top Winchester Hotel Reviews

Best Western Plus Richmond Indiana I-70

Hampton Inn & Suites Muncie

Randolph Inn and Suites

Fairfield Inn by Marriott Muncie

Hampton Inn & Suites Richmond, IN

Home2 Suites By Hilton Muncie

Comfort Inn & Suites Muncie Near University

More cheap stays in Winchester

Motel 6 Richmond, IN

Days Inn by Wyndham Muncie -Ball State University

Quality Inn and Conference Center

Baymont by Wyndham Richmond I-70

Best Western Plus Richmond Indiana I-70

Comfort Suites Richmond East

Frequently asked questions

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