Book Hotels in Bennington, IN

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Top Bennington hotels

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Madison IN
This cabin includes a garden and barbecue grills.
We arrived at the cabin at dark. The cabin appeared very cute. The host provided the arrival info via email. The cabin was very cute and very clean. Everything was provided and all instructions as well. My husband an I were there for a peaceful getaway from the city. The cabin met all of our needs ...

Reviewed on Jan 22, 2026

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Opens in a new window1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

2.5 out of 5
108 ST. MICHAELS AVENUE Madison IN
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Mar 8 to Mar 9
$155 total
Mar 8 - Mar 9
Total with taxes and fees
This hotel features a gym and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental ...
love it

Reviewed on Feb 25, 2026

Opens in a new windowFairfield Inn & Suites Madison Historic Eagle Cotton Mill
Empire House Hotel

Empire House Hotel

2.5 out of 5
114 South Front street Rising Sun IN
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Mar 23 to Mar 24
$66 total
Mar 23 - Mar 24
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
Room was so nice and cozy. The owner, Marsha was wonderful and I appreciated the hospitality.

Reviewed on Feb 24, 2026

Opens in a new windowEmpire House Hotel
Comfort Inn Madison near Clifty Falls

Comfort Inn Madison near Clifty Falls

2.5 out of 5
3767 Clifty Dr Madison IN
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Mar 8 to Mar 9
$107 total
Mar 8 - Mar 9
Total with taxes and fees
This hotel features an indoor pool and a sauna. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
Room and pillows musty. Water was lukewarm unless you run it for 5 minutes. Breakfast was good for the money paid for one night.

Reviewed on Feb 21, 2026

Opens in a new windowComfort Inn Madison near Clifty Falls
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
777 Belterra Drive Florence IN
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $164 total per night from Mar 2 to Mar 3
$164 total
Mar 2 - Mar 3
Total with taxes and fees
This hotel features a golf course, a casino, and 3 restaurants. Traveling on business? Take advantage of the business center, laundry service, and free valet ...
Room was clean. Staff was great!

Reviewed on Mar 1, 2026

Opens in a new windowBelterra Casino Resort
Hillside Inn

Hillside Inn

2.5 out of 5
831 E Main St Madison IN
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Mar 2 to Mar 3
$102 total
Mar 2 - Mar 3
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi ...
Excellent staff!

Reviewed on Feb 21, 2026

Opens in a new windowHillside Inn
Holiday Inn Express Hotel & Suites Madison by IHG

Holiday Inn Express Hotel & Suites Madison by IHG

2.5 out of 5
300 Franks Dr Madison IN
Fully refundable
$112 nightly
The price is $129 total per night from Mar 30 to Mar 31
$129 total
Mar 30 - Mar 31
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests ...
It was nice and clean, your basic Holiday Inn Express. The pool was very clean nice and crystal clear. It wasn't overpowering with chlorine like most hotel pools. And warm enough, you could just walk straight into it.

Reviewed on Feb 15, 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Madison by IHG
Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

2.5 out of 5
525 Dale Drive I 71 Exit 57 Sp Sparta KY
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $86 total per night from Mar 2 to Mar 3
$86 total
Mar 2 - Mar 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
Clean reoom amd friendly steff

Reviewed on Feb 9, 2026

Opens in a new windowRamada by Wyndham Sparta/At Speedway
Rising Star Casino Resort

Rising Star Casino Resort

2 out of 5
777 Rising Star Drive Rising Sun IN
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Mar 2 to Mar 3
$124 total
Mar 2 - Mar 3
Total with taxes and fees
A golf course, 3 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and snack bar/deli.
Clean room. Very nice staff.

Reviewed on Feb 18, 2026

Opens in a new windowRising Star Casino Resort
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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.

Frequently asked questions

What are the top kid-friendly hotels in Bennington?
Take some of the worries out of traveling with kids by opting for a family-friendly Bennington hotel. From entertaining amenities to services that bring a smile, these stays offer perks that'll make your getaway plain sailing: Your gang will enjoy their time at Carol's Cabin in the Woods in Historic Hoosier Hills. A playground and a firepit are among the things that help make this hotel a favorite. Secluded Country Home in Historic Hoosier Hills is another top pick. After a long day of exploring, return to your comfy room and amenities like a playground and animal viewing activities.
Where can I find cheap hotels in Bennington?
At Travelocity you'll find really nice hotels in Bennington at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Bennington rather than in Bennington. We may find you even better rates, too.
How do I find the best Bennington hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Bennington then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Bennington?
The cheapest hotel in Bennington is $66. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Bennington?
There are 152 hotels in Bennington on Travelocity.
What are the best hotels in Bennington?
Bennington has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Bennington for you!
When is the best time to visit Bennington?
If you want the joy of a fun-filled trip in peak season, visit Bennington during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Bennington?
Based on historic data is usually the cheapest month to visit Bennington. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Bennington?
There are multiple hotels in Bennington that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Bennington. We have plenty of kid-friendly hotels in Bennington to choose from on Travelocity!
Why book a hotel in Bennington through Travelocity?
Because we have the top hotels in Bennington! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Bennington on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Bennington hotel reviews by fellow wanderers

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"love it"
A verified traveler stayed at Fairfield Inn & Suites Madison Historic Eagle Cotton Mill
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill