Top 10 Hotels in Bennington, IN (from $62) 2026 - Competitive Prices

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Our top choices for Bennington hotels

A balcony with a metal railing and a round table with a chair.

A multi-story hotel with balconies and a curved section.

A hotel room with a dining area, kitchenette, and a view through the door.

A hallway with a stone planter, a staircase, and a door leading to another room.

1. Hillside Inn

Madison Historic District

Autumn

$89 nightly

$102 total

Oct 18 - Oct 19

Total with taxes and fees

A room with two beds, a flat-screen TV, and a large window.

A living room with a beige sofa, a round coffee table, and a dining table with chairs.

A sign for the Fairway Inn with a clear view of the sky in the background.

A dining area with a table set for two, a kitchen in the background, and a hallway leading to another room.

2. Fairway Inn Florence

Florence

Jeffrey

$75 nightly

$84 total

Oct 18 - Oct 19

Total with taxes and fees

A spacious lounge with a stone fireplace, comfortable seating, and large windows offering views of the outdoors.

A building with a stone facade, large windows, and a stone retaining wall.

A spacious room with large wooden-framed windows, a central seating area with a sofa and armchairs, and a small table.

A spacious room with wooden floors and large arched windows, featuring multiple seating areas and tables.

3. General Butler State Resort Park

Carrollton

Maxine

$117 nightly

$129 total

Oct 18 - Oct 19

Total with taxes and fees

An outdoor dining area with wooden tables and chairs, large windows, and a view of a lake.

A hotel entrance with a brick facade, a white entrance door, and a blue sign above it. There are golf carts parked on either side of the entrance.

A bar area with wooden furnishings, a long table, and a staircase.

A Riverboat Inn with a covered deck area, outdoor seating, and a signboard advertising amenities like a bar, pool, and WiFi.

4. Riverboat Inn and Suites

Madison Historic District

Katherine

$107 nightly

$123 total

Oct 18 - Oct 19

Total with taxes and fees

A large, multi-story hotel with a prominent dome and arched windows, featuring a well-lit entrance and landscaped gardens.

A golf course with a flag, a sand bunker, and a building in the background.

A hotel room with a large bed, two bedside tables, a chair, and a view of a lake.

A poolside area with lounge chairs and a towel with a monogram.

5. Belterra Casino Resort

Florence

Tane

$155 nightly

$173 total

Oct 20 - Oct 21

Total with taxes and fees

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a counter.

A hotel room with two beds, a nightstand with a lamp, and a window with blinds.

A hotel room with a blue sofa, a wooden dresser, a flat-screen TV, and a framed artwork on the wall.

A desk with two HP printers, a keyboard, and a mouse. There are two monitors displaying desktop backgrounds.

6. Holiday Inn Express Hotel & Suites Madison by IHG

Madison

Dawn

$105 nightly

$121 total

Nov 1 - Nov 2

Total with taxes and fees

A two-story building with a balcony, multiple windows, and a sign indicating it is a hotel.

A bedroom with a wooden bed, floral bedding, a bedside table with a lamp, and a wall with floral wallpaper.

A two-story building with a balcony on the upper floor, a covered porch with seating, and a front door with a small porch area.

A hotel room with a bed, a television on a wooden stand, a small table, and a chair.

7. Empire House Hotel

Rising Sun

Sheri

$55 nightly

$62 total

Oct 16 - Oct 17

Total with taxes and fees

A modern bar area with a long counter, multiple stools, and a well-stocked liquor display.

A modern bar area with a variety of liquor bottles and glasses, a seating area with leather sofas and chairs, and a large window providing natural light.

A covered outdoor seating area with wicker furniture and a brick building in the background.

A large brick building with a flat roof, a parking lot, and a bridge in the background.

8. Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Madison Historic District

Michael

$161 nightly

$185 total

Oct 25 - Oct 26

Total with taxes and fees

A modern living room with a stone fireplace, a flat-screen TV, and a sofa.

A modern kitchen with a microwave, coffee maker, and a large refrigerator.

A hotel gym with cardio machines, free weights, and a mirror.

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

9. Quality Inn Carrollton

Carrollton

Teresa

$68 nightly

$75 total

Nov 13 - Nov 14

Total with taxes and fees

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

A multi-story hotel with a covered entrance and a sign indicating it is a Ramada hotel.

A hotel room with a dark blue sofa, a small table, a TV mounted on the wall, and a window with curtains.

A small kitchenette with a refrigerator, an ATM, and a snack shelf.

10. Ramada by Wyndham Sparta/At Speedway

Sparta

Julie

$58 nightly

$64 total

Oct 28 - Oct 29

Total with taxes and fees

A hotel room with two beds, a red armchair, and a nightstand with lamps.

A dining area with a table and chairs, a kitchenette, and a pantry.

A bathroom with a white sink, a black faucet, and a blue Pepsi vending machine.

A Red Roof Inn with a covered entrance, a clear sky, and a flag.

11. Red Roof Inn Carrollton

Carrollton

Joseph

$62 nightly

$68 total

Oct 21 - Oct 22

Total with taxes and fees

A hotel room with two beds, each with a patterned bedspread, a large wall painting of a waterfall, and two wall-mounted lamps.

A hotel lobby with a reception desk, a sofa, a dining table with chairs, and a kitchen area.

A living room with a fireplace, a flat-screen TV mounted above it, and a window with blinds.

A hotel lobby with a seating area, a television, and a view of the parking lot through the glass doors.

12. Super 8 by Wyndham Madison IN

Madison

Erin

$69 nightly

$79 total

Nov 2 - Nov 3

Total with taxes and fees

A Comfort Inn hotel with a gas station attached, featuring a stone facade and multiple windows.

A hotel room with a large bathtub, a sofa, a television, and framed pictures on the wall.

A covered outdoor seating area with picnic tables and benches, surrounded by landscaped gardens and trees.

A modern hotel lobby with a blue sofa, a fireplace, a television, and a dining area.

13. Comfort Inn Madison near Clifty Falls

Madison

Jodi

$93 nightly

$107 total

Nov 8 - Nov 9

Total with taxes and fees

An indoor swimming pool with a glass ceiling, concrete floor, and white chairs around the pool.

A West Way Inn with a brick facade, a covered parking area, and a clear sky.

A small, well-lit cafe with wooden cabinets, a counter with various food items, a coffee machine, and a clock on the wall.

A reception area with a wooden counter, two wall-mounted lamps, a clock, and a framed map on the wall.

14. Best Way Inn Madison

Madison

Chad

$79 nightly

$91 total

Oct 18 - Oct 19

Total with taxes and fees

A lobby with two red sofas, a reception desk, and a snack vending machine.

A kitchen with a checkered floor, wooden cabinets, and a chalkboard wall with kitchen-related drawings and text.

15. Hampton Inn Carrollton

Carrollton

Krista

$174 nightly

$192 total

Oct 17 - Oct 18

Total with taxes and fees

A bed with white bedding and pillows against a wooden headboard.

A multi-story hotel with a clear entrance and a covered parking area.

A clean, well-organized snack and beverage area with shelves stocked with various snacks and a refrigerated display case.

A reception area with a modern design, featuring a reception desk, a digital display, and a check-in counter.

16. Holiday Inn Express & Suites Carrollton by IHG

Carrollton

Mark

$151 nightly

$166 total

Nov 14 - Nov 15

Total with taxes and fees

A spacious living room with a green sofa, a leather armchair, and a wooden coffee table. A brick wall and a chandelier are visible.

The exterior of The Chandler Hotel with a prominent illuminated sign, large windows, and a visible door.

A corridor with framed pictures on the walls, a person holding a glass of wine, and a light fixture on the ceiling.

A spacious living room with a brick wall, a staircase, and a green sofa.

17. The Chandler Hotel

Madison Historic District

michael

$171 nightly

$197 total

Oct 18 - Oct 19

Total with taxes and fees

A building with large windows and a sign that reads "Tanglewood Antiques."

A spacious interior with a brick wall, a wooden staircase, and a large window offering a view of the outside.

An interior view of a brick-walled dining area with tables and chairs.

A rustic venue with exposed wooden beams, brick walls, and tables set for dining.

18. The Tanglewood

Versailles

Beth

$142 nightly

$159 total

Oct 18 - Oct 19

Total with taxes and fees

A hotel room with two beds, a desk, a chair, a TV, and a large waterfall painting on the wall.

The Carroll County Courthouse with a brick facade, a flagpole, and a lawn in front.

Two front-loading Whirlpool washers in a laundry room with wooden paneling and a tiled floor.

A hotel lobby with a leather sofa, glass coffee table, and two lamps.

19. Super 8 by Wyndham Carrollton

Carrollton

Eric

$77 nightly

$84 total

Nov 1 - Nov 2

Total with taxes and fees

A spacious bar area with multiple screens displaying sports events, a variety of seating arrangements, and a prominent 'Rising Star Casino & Resort' sign.

A hotel room with two beds, a sofa, a small ottoman, and a television.

A swimming pool with lounge chairs and a person swimming.

A group of people gathered around a casino table with chips and cards, indicating a gambling activity.

20. Rising Star Casino Resort

Rising Sun

Earl

$102 nightly

$114 total

Nov 15 - Nov 16

Total with taxes and fees

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Top Bennington Hotel Reviews

Super 8 by Wyndham Madison IN

8/10 Good

"Not exceptional, just average."

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

10/10 Excellent

"Beautiful place to stay in Chattanooga. The place was immaculate and well stocked with everything we needed."

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

8/10 Good

"The staff went above and beyond to help us. They made the extra effort to make our stay special. The view was spectacular and the room was comfortable and quiet. I would definitely recommend staying there."

Rising Star Casino Resort

10/10 Excellent

"Room was very clean and comfortable"

Quality Inn Carrollton

10/10 Excellent

"The hotel is very convenient to the highway. We stayed one night and it fit our need perfectly. Not a lot of room amenities but for one night it didn’t matter. It was clean, quiet and comfortable. The only thing that was a tiny bit bothersome was the wide gap at the bottom of the entry door. It let in a lot of light all night but actually served as a night light. B’fast was the usual quick bagel, muffin, waffle iron, etc. It served the purpose before we hit the road. I would stay again."

Hillside Inn

10/10 Excellent

"If you are looking to stay in an older Historic hotel with a great view give this one a try. The rooms are nicely finished and have as many modern amenities as one would expect. Your own private balcony is a real plus with views of the Ohio river and down town Madison. Walking to either is easy from this location as well if you so desire. The lobby is a neat tidy greeting place with it's own coy pond. Pictures of the original hotel in it's several iterations adorn the walls. One dating back to 1870! We enjoyed our stay and would highly recommend the experience."

Holiday Inn Express Hotel & Suites Madison by IHG

8/10 Good

"It was a very nice stay. The only thing that would have been helpful would be the check in time. Checking in a four was a bit late in the day."

The Chandler Hotel

10/10 Excellent

"Beautiful place to stay. Well appointed. Finished carpentry is beautiful."

Best Way Inn Madison

8/10 Good

"Decent place to stay. Affordable."

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