Bennington Chalets

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Chalets in Bennington

No exact matches found, but these alternatives could be just right

Recommended hotels in Bennington

Exterior
Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

2.5 star property
Sparta
7.8 out of 10, Good, (1007)
"Everything was perfect "
United States
danny
$72 nightly
The price is $80
Dec 26 - Dec 27
Total with taxes and fees
Ramada by Wyndham Sparta/At Speedway
Indoor pool
Rising Star Casino Resort

Rising Star Casino Resort

2.0 star property
Rising Sun
8.0 out of 10, Very Good, (601)
"Staff was helpful at main hotel. Room clean & parking was plentiful "
United States
Shari
$110 nightly
The price is $124
Dec 7 - Dec 8
Total with taxes and fees
Rising Star Casino Resort
Exterior
Comfort Inn Madison near Clifty Falls

Comfort Inn Madison near Clifty Falls

2.5 star property
Madison
8.8 out of 10, Excellent, (659)
"Great stay, clean, and comfy bed!"
United States
cheryl
$93 nightly
The price is $107
Dec 14 - Dec 15
Total with taxes and fees
Comfort Inn Madison near Clifty Falls
Exterior
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
$69 nightly
The price is $77
Dec 5 - Dec 6
Total with taxes and fees
Empire House Hotel
Balcony
Hillside Inn

Hillside Inn

2.5 star property
Madison
8.6 out of 10, Excellent, (1007)
" The staff was very friendly. "
United States
Kenneth
$80 nightly
The price is $92
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hillside Inn
Exterior
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
$75 nightly
The price is $84
Dec 7 - Dec 8
Total with taxes and fees
Fairway Inn Florence
Exterior
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, (391)
"Beautiful hotel, rooms were exceptionally clean, service was so friendly. Love this place and will return."
United States
Paul
$135 nightly
The price is $155
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill
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
$129 nightly
The price is $145
Dec 14 - Dec 15
Total with taxes and fees
Belterra Casino Resort
Exterior
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, (569)
"The room was clean and the staff was friendly. "
United States
Amy
$95 nightly
The price is $109
Dec 11 - Dec 12
Total with taxes and fees
Holiday Inn Express Hotel & Suites Madison by IHG
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
$85 nightly
The price is $94
Dec 11 - Dec 12
Total with taxes and fees
Super 8 by Wyndham Carrollton
Front of property
The Tanglewood

The Tanglewood

2.0 star property
Versailles
9.2 out of 10, Wonderful, (5)
"Great place! Clean room and good communication from staff. "
United States
Bonnie
$138 nightly
The price is $155
Dec 9 - Dec 10
Total with taxes and fees
The Tanglewood
Exterior
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
$68 nightly
The price is $75
Jan 3 - Jan 4, 2026
Total with taxes and fees
Quality Inn
Front of property
The Chandler Hotel

The Chandler Hotel

2.0 star property
Madison
10.0 out of 10, Exceptional, (119)
"Lovely hotel, great stay!"
United States
Julie
$145 nightly
The price is $167
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$139 nightly
The price is $154
Dec 13 - Dec 14
Total with taxes and fees
General Butler State Resort Park
Exterior
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
$53 nightly
The price is $59
Dec 7 - Dec 8
Total with taxes and fees
Hillcrest Motel By OYO Aurora IN Near Lawrenceburg
Terrace/patio
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
$286 nightly
The price is $316
Dec 7 - Dec 8
Total with taxes and fees
Riverside Inn Bed and Breakfast
Exterior
Hampton Inn Carrollton

Hampton Inn Carrollton

2.5 star property
Carrollton
8.2 out of 10, Very Good, (301)
"Convenient location and friendly staff"
United States
Tricia
$143 nightly
The price is $158
Dec 10 - Dec 11
Total with taxes and fees
Hampton Inn Carrollton
Exterior
The Blue Door Place

The Blue Door Place

Florence
9.6 out of 10, Exceptional, (18)
"Perfect spot "
United States
Damon G.
$120 nightly
The price is $134
Dec 8 - Dec 9
Total with taxes and fees
The Blue Door Place
Exterior
Super 8 by Wyndham Madison IN

Super 8 by Wyndham Madison IN

2.0 star property
Madison
6.8 out of 10, (416)
"Upgraded at check in, friendly staff"
United States
Sarah
$74 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Super 8 by Wyndham Madison IN
Exterior
Riverboat Inn and Suites

Riverboat Inn and Suites

3.0 star property
Madison
9.4 out of 10, Exceptional, (102)
"The room and staff were great. Enjoyed our stay."
United States
Katrina
$93 nightly
The price is $108
Jan 4 - Jan 5, 2026
Total with taxes and fees
Riverboat Inn and Suites
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"We had a wonderful time in Madison. The hotel is quite charming and the history behind it is so fascinating. There are some minor updates that need to be repaired in Room 104, but overall, it's fine. Merry Christmas! "
Thomas 2-night trip
Posted 3 days ago
Hillside Inn

Find out more about Bennington

Bennington Chalets information

Number of reviews
7,396
Accommodation
1 Chalets
Lowest Price
$59
Highest Price
$316

Explore a world of travel with Expedia