Top 10 Hotels in Bennington, IN (from $53) 2026 - Competitive Prices

Go beyond your typical stay in Bennington

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Our top choices for Bennington hotels

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

A hotel room with a large bed, a separate bed, a sitting area with a chair, a desk, a fireplace, and a view of the outdoors.

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

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

1. Hillside Inn

Madison Historic District

Kelly

$89 nightly

$102 total

Oct 25 - Oct 26

Total with taxes and fees

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

A compact hotel room with a sofa, a small wooden table, a kitchenette, and a TV mounted on the wall.

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

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

2. Holiday Inn Express Hotel & Suites Madison by IHG

Madison

Dawn

$99 nightly

$114 total

Nov 22 - Nov 23

Total with taxes and fees

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

A deck with two chairs and a table, overlooking a river and a bridge.

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.

3. Riverboat Inn and Suites

Madison Historic District

Katherine

$98 nightly

$113 total

Nov 22 - Nov 23

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 swimming pool with lounge chairs, a building with a sloped roof, and a stone wall.

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

4. General Butler State Resort Park

Carrollton

Maxine

$117 nightly

$129 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

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

5. Ramada by Wyndham Sparta/At Speedway

Sparta

Julie

$59 nightly

$64 total

Oct 25 - Oct 26

Total with taxes and fees

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

A motel with a large parking lot and a covered entrance.

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.

6. Fairway Inn Florence

Florence

Jeffrey

$75 nightly

$84 total

Oct 25 - Oct 26

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

A gym with multiple treadmills, stationary bikes, and other cardio equipment.

7. Belterra Casino Resort

Florence

Tane

$138 nightly

$154 total

Nov 15 - Nov 16

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 small kitchenette with a microwave, coffee maker, and a sink.

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.

8. Empire House Hotel

Rising Sun

William

$48 nightly

$53 total

Oct 29 - Oct 30

Total with taxes and fees

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

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

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

A spacious living area with a stone wall, modern furniture, and large windows offering a view of the outdoors.

9. Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Madison Historic District

Michael

$161 nightly

$185 total

Nov 1 - Nov 2

Total with taxes and fees

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

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.

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

10. Comfort Inn Madison near Clifty Falls

Madison

Jodi

$92 nightly

$106 total

Nov 15 - Nov 16

Total with taxes and fees

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

A hotel reception area with a modern design, featuring a mosaic wall, a reception desk, and a digital display.

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

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

11. Quality Inn Carrollton

Carrollton

Teresa

$68 nightly

$75 total

Nov 20 - Nov 21

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 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.

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

12. Super 8 by Wyndham Madison IN

Madison

Erin

$69 nightly

$79 total

Nov 1 - Nov 2

Total with taxes and fees

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

A lobby with an ATM, a reception desk, a clock, and a staircase leading to another area.

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.

13. Red Roof Inn Carrollton

Carrollton

Joseph

$62 nightly

$68 total

Oct 28 - Oct 29

Total with taxes and fees

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

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

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.

14. Best Way Inn Madison

Madison

Chad

$79 nightly

$91 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

A modern coffee shop with a black table, wooden chairs, a sofa, and a coffee machine.

15. Holiday Inn Express & Suites Carrollton by IHG

Carrollton

Mark

$155 nightly

$171 total

Nov 19 - Nov 20

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 golf course with a clubhouse, a golf cart, and a person preparing to hit a golf ball.

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

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

16. Rising Star Casino Resort

Rising Sun

Earl

$110 nightly

$124 total

Oct 25 - Oct 26

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.

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

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.

17. The Chandler Hotel

Madison Historic District

michael

$171 nightly

$197 total

Oct 26 - Oct 27

Total with taxes and fees

A hotel room with two beds, a desk with a computer, a chair, a TV, and a window with a view of trees.

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

18. Hampton Inn Carrollton

Carrollton

Krista

$174 nightly

$192 total

Oct 24 - Oct 25

Total with taxes and fees

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

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.

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

19. The Tanglewood

Versailles

Beth

$151 nightly

$169 total

Oct 25 - Oct 26

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.

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

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

20. Super 8 by Wyndham Carrollton

Carrollton

Eric

$69 nightly

$76 total

Oct 28 - Oct 29

Total with taxes and fees

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Top Bennington Hotel Reviews

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent

"The motel is under a little construction. But our stay was great. It is at a peaceful location. We saw deer out the window different times. The breakfast was very good and there was always plenty of it. We will be staying there if we are that way in our travels again."

Super 8 by Wyndham Madison IN

10/10 Excellent

"Will be staying here a lot when we take a weekend getaway 🍿🍿"

The Chandler Hotel

8/10 Good

"The property was in an excellent location. Close to many restaurants and the river walk. Really enjoyed walking downtown. The room was nice. We like having a kitchenette. It could have been a little quieter. Could hear the upstairs shower and water running. But over all like this place to stay."

Riverboat Inn and Suites

8/10 Good

"The bed was comfortable, bathroom was clean, coffee good, breakfast ok, close to river walk. Furnishings/decor didn’t seem functional for a hotel stay, like not having a convenient place to put your suitcase in the bedroom area. An older property."

Hillside Inn

10/10 Excellent

"Very helpful at check in, great room with a balcony and view, nice breakfast, centrally located."

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

10/10 Excellent

"The receptionist was wonderful !! A lot of help and very friendly. Would recommend stating there and will go back again"

Holiday Inn Express Hotel & Suites Madison by IHG

8/10 Good

"Na"

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."

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

10/10 Excellent

"Super cute little cottage close to an expansive downtown area on the river, but far enough out of town to have some privacy. We only stayed for a night on a long trek home but a perfect little place. Would return to check out the downtown area!"

More cheap stays in Bennington

Ramada by Wyndham Sparta/At Speedway

525 Dale Drive I 71 Exit 57 Sp Sparta KY

$59 nightly

$64 total

Oct 25 - Oct 26

Total with taxes and fees

7.8/10 Good! (1,002 reviews)

Quality Inn Carrollton

141 Inn Road Carrollton KY

$68 nightly

$75 total

Nov 20 - Nov 21

Total with taxes and fees

Best Way Inn Madison

700 Clifty Drive Madison IN

$79 nightly

$91 total

Oct 25 - Oct 26

Total with taxes and fees

Hillside Inn

831 E Main St Madison IN

$89 nightly

$102 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (1,004 reviews)

Comfort Inn Madison near Clifty Falls

3767 Clifty Dr Madison IN

$92 nightly

$106 total

Nov 15 - Nov 16

Total with taxes and fees

Holiday Inn Express Hotel & Suites Madison by IHG

300 Franks Dr Madison IN

$99 nightly

$114 total

Nov 22 - Nov 23

Total with taxes and fees

8.4/10 Very Good! (617 reviews)

Hotels in Bennington with star-rating

Frequently asked questions

Where is the best place for a stay in Bennington?

Located 12.1 mi (19.5 km) from the heart of Bennington, Belterra Casino Resort is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Ramada by Wyndham Sparta/At Speedway and Quality Inn Carrollton. See all available top hotels, or vacation rentals in Bennington.

What are some of the best vacation rentals in Bennington?

Red comfy cottage: Visitors like this Bennington vacation home rental. It offers an indoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Bennington.

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

Yes! The majority of hotel reservations are fully refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Bennington.

Where can I learn more about changing or cancelling my trip to Bennington?

For additional details about picking new dates or cancelling your trip to Bennington, click here.

What's it like staying in Bennington?

Those traveling to Bennington are sure to enjoy the sights to see and things to do. There are 175 hotels and other accommodations in the surrounding area. Find out more about Bennington.

What should I do while I'm visiting Bennington?

Places to visit in the wider area include Belterra Casino, General Butler State Resort Park, and Versailles State Park. You'll also find Historic District and Schofield House in the area. Check out what more to see and do in Expedia's Bennington guide.

What's the seasonal weather like in Bennington?

The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Bennington is 50 inches.

Find hotels in Bennington, IN from $53

Go beyond your typical stay in Bennington

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Bennington hotels

1. Hillside Inn

2. Holiday Inn Express Hotel & Suites Madison by IHG

3. Riverboat Inn and Suites

4. General Butler State Resort Park

5. Ramada by Wyndham Sparta/At Speedway

6. Fairway Inn Florence

7. Belterra Casino Resort

8. Empire House Hotel

9. Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

10. Comfort Inn Madison near Clifty Falls

11. Quality Inn Carrollton

12. Super 8 by Wyndham Madison IN

13. Red Roof Inn Carrollton

14. Best Way Inn Madison

15. Holiday Inn Express & Suites Carrollton by IHG

16. Rising Star Casino Resort

17. The Chandler Hotel

18. Hampton Inn Carrollton

19. The Tanglewood

20. Super 8 by Wyndham Carrollton

Top Bennington Hotel Reviews

Ramada by Wyndham Sparta/At Speedway

Super 8 by Wyndham Madison IN

The Chandler Hotel

Riverboat Inn and Suites

Hillside Inn

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Holiday Inn Express Hotel & Suites Madison by IHG

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

More cheap stays in Bennington

Ramada by Wyndham Sparta/At Speedway

Quality Inn Carrollton

Best Way Inn Madison

Hillside Inn

Comfort Inn Madison near Clifty Falls

Holiday Inn Express Hotel & Suites Madison by IHG

Hotels in Bennington with star-rating

Frequently asked questions

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