Bennington Hotels

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Tonight
6 Dec - 7 Dec
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7 Dec - 8 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Top 10 trending Bennington hotels

Property amenity
Hillside Inn

Hillside Inn

2.5 star property
Madison
8.6 out of 10, Excellent, (1001)
"Great view, friendly staff."
United States
Roy
The price is €79
includes taxes & fees
1 Jan - 2 Jan 2026
Hillside Inn
Exterior
Riverboat Inn and Suites

Riverboat Inn and Suites

3.0 star property
Madison
9.4 out of 10, Exceptional, (103)
"The room and staff were great. Enjoyed our stay."
United States
Katrina
The price is €96
includes taxes & fees
4 Jan - 5 Jan 2026
Riverboat Inn and Suites
Free buffet breakfast
Holiday Inn Express Hotel & Suites Madison by IHG

Holiday Inn Express Hotel & Suites Madison by IHG

2.5 star property
Madison
8.4 out of 10, Very good, (570)
"The room was clean and the staff was friendly. "
United States
Amy
The price is €104
includes taxes & fees
9 Dec - 10 Dec
Holiday Inn Express Hotel & Suites Madison by IHG
Meeting facility
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

2.5 star property
Madison
9.8 out of 10, Exceptional, (392)
"Beautiful hotel, rooms were exceptionally clean, service was so friendly. Love this place and will return."
United States
Paul
The price is €133
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill
Exterior
Comfort Inn Madison near Clifty Falls

Comfort Inn Madison near Clifty Falls

2.5 star property
Madison
8.8 out of 10, Excellent, (660)
"Great stay, clean, and comfy bed!"
United States
cheryl
The price is €92
includes taxes & fees
14 Dec - 15 Dec
Comfort Inn Madison near Clifty Falls
Indoor pool, pool loungers
Best Way Inn Madison

Best Way Inn Madison

2.5 star property
Madison
6.8 out of 10, (522)
"Very clean room"
United States
Arnulfo
The price is €68
includes taxes & fees
1 Jan - 2 Jan 2026
Best Way Inn Madison
Free daily on-the-go breakfast
Super 8 by Wyndham Madison IN

Super 8 by Wyndham Madison IN

2.0 star property
Madison
6.8 out of 10, (417)
"Good service … "
United States
Reuel
The price is €76
includes taxes & fees
4 Jan - 5 Jan 2026
Super 8 by Wyndham Madison IN
BBQ/picnic Area
Hillcrest Motel By OYO Aurora IN Near Lawrenceburg

Hillcrest Motel By OYO Aurora IN Near Lawrenceburg

2.5 star property
Aurora
6.4 out of 10, (44)
"Great Place to stay!"
United States
Paul
The price is €45
includes taxes & fees
20 Dec - 21 Dec
Hillcrest Motel By OYO Aurora IN Near Lawrenceburg
Exterior
Belterra Casino Resort

Belterra Casino Resort

3.5 star property
Florence
8.6 out of 10, Excellent, (1001)
"Room was clean and the staff was good."
United States
Gary
The price is €124
includes taxes & fees
14 Dec - 15 Dec
Belterra Casino Resort
Dining
Fairway Inn Florence

Fairway Inn Florence

2.0 star property
Florence
8.4 out of 10, Very good, (52)
"Convenient to where we needed to go. "
United States
Walter
The price is €65
includes taxes & fees
8 Dec - 9 Dec
Fairway Inn Florence
Indoor pool
Rising Star Casino Resort

Rising Star Casino Resort

2.0 star property
Rising Sun
8.0 out of 10, Very good, (602)
"Staff was helpful at main hotel. Room clean & parking was plentiful "
United States
Shari
The price is €106
includes taxes & fees
8 Dec - 9 Dec
Rising Star Casino Resort
Front of property
Empire House Hotel

Empire House Hotel

2.5 star property
Rising Sun
9.2 out of 10, Wonderful, (321)
"Marsha, the hostess was wonderful. To be able to sit on the porch and look at the river was amazing. "
United States
Charlene
Empire House Hotel
Outdoor banquet area
Riverside Inn Bed and Breakfast

Riverside Inn Bed and Breakfast

3.0 star property
Warsaw
10.0 out of 10, Exceptional, (1)
"Beautiful "
United States
Danielle
The price is €271
includes taxes & fees
4 Jan - 5 Jan 2026
Riverside Inn Bed and Breakfast
Miscellaneous
Super 8 by Wyndham Carrollton

Super 8 by Wyndham Carrollton

2.0 star property
Carrollton
7.6 out of 10, Good, (27)
"Staff help was great "
United States
Daryl
The price is €80
includes taxes & fees
13 Dec - 14 Dec
Super 8 by Wyndham Carrollton
Restaurant
Hampton Inn Carrollton

Hampton Inn Carrollton

2.5 star property
Carrollton
8.2 out of 10, Very good, (301)
"Abigail was awesome. She is very professional and attentive to guest needs. The breakfast is not very exciting but it works. The room was clean and comfortable. All in All i was very please. "
United States
Daryl
The price is €136
includes taxes & fees
13 Dec - 14 Dec
Hampton Inn Carrollton
Exterior
Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

2.5 star property
Sparta
7.8 out of 10, Good, (1000)
"Everything was perfect "
United States
danny
The price is €80
includes taxes & fees
14 Dec - 15 Dec
Ramada by Wyndham Sparta/At Speedway
Luxury Room
The Chandler Hotel

The Chandler Hotel

2.0 star property
Madison
10.0 out of 10, Exceptional, (120)
"The room and facility were amazing. Old world charm in the middle of downtown Madison, IN. Just about everything was within walking distance. We had a fantastic stay and thoroughly enjoyed our time spent here."
United States
Shannon
The price is €143
includes taxes & fees
6 Jan - 7 Jan 2026
The Chandler Hotel
Balcony view
General Butler State Resort Park

General Butler State Resort Park

3.0 star property
Carrollton
8.2 out of 10, Very good, (448)
"Nice stay"
United States
Beverly B.
General Butler State Resort Park
Free daily self-service breakfast
Quality Inn

Quality Inn

2.5 star property
Carrollton
7.6 out of 10, Good, (309)
"Yes clean room great condition "
United States
Efrain Perez
The price is €64
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn
Loft, 1 King Bed, Kitchen
East Main Lofts

East Main Lofts

2.0 star property
Madison
8.0 out of 10, Very good, (4)
"Great location! Room was clean and spacious. Just like the pictures. Easy check in and check out."
United States
Kathleen
The price is €199
includes taxes & fees
8 Dec - 9 Dec
East Main Lofts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"While an older hotel and not modern, our stay was clean and quiet. Parking can be a little tight since no one seems to park within the lines anymore. The view from the balconies is unmatched. You can see all the way down main street, and at Christmas time, is a beautiful view."
Shannon 1-night trip
Posted 2 days ago
Hillside Inn

More cheap stays in Bennington

Best Way Inn Madison

Best Way Inn Madison

700 Clifty Drive Madison IN
The price is €68 per night from 1 Jan to 2 Jan
€68
1 Jan - 2 Jan 2026
includes taxes & fees
6.8/10 (522 reviews)

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 traveller data. Two other options for your visit to the area are Ramada by Wyndham Sparta/At Speedway and Comfort Inn Madison near Clifty Falls. See all available top hotels, or vacation rentals in Bennington.
What are some of the best holiday rentals that Bennington has to offer?
Glenda's Overlook..everything you need to make visiting Madison a great getaway!: This holiday home rental outside of Bennington offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 cancelled before the hotel's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Bennington.
How is it to stay in Bennington?
Those travelling to Bennington will definitely enjoy the sights to see and things to do. There are 155 hotels and other accommodation options in the surrounding area. Find out more about Bennington.
What is there to see in Bennington?
Places to visit in the wider area include The Ridge Winery Tasting Room, Belterra Casino and General Butler State Resort Park. You'll also find Versailles State Park and Historic District in the area. Take a look at what more there is 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 temperature of 23°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Bennington is 1273 mm.

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