Compare Cheap Hotels in Old Bennington
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Cheap Old Bennington Hotels
The Four Chimneys Inn
21 West Road Bennington VT
$249 nightly
The price is $271 total per night
$271 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
0.2 mi from city center
Located in Bennington, The Four Chimneys Inn is next to a golf course, a 4-minute walk from Old First Congregational Church and 10 minutes by foot from Bennington Museum.
The Williams Inn
101 Spring Street Williamstown MA
$197 nightly
The price is $220 total per night
$220 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.01 mi from city center
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Pet friendly
Parking included
Mount Snow Grand Summit Resort
89 Grand Summit Way West Dover VT
$243 nightly
The price is $268 total per night
$268 total
Dec 15 - Dec 16
Total with taxes and fees
17.11 mi from city center
Located in West Dover, Mount Snow Grand Summit Resort is a 1-minute drive from Mount Snow and 8 minutes from Mount Snow Golf Course.
Pool
Hot Tub
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$124 nightly
The price is $139 total per night
$139 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
Free Cancellation
13.69 mi from city center
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Valley Craft Ales
18 N Main St Wilmington VT
$153 nightly
The price is $168 total per night
$168 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
17.41 mi from city center
Located in Wilmington, Valley Craft Ales is in the historical district, a 4-minute drive from Harriman Reservoir and 6 minutes from Molly Stark State Park.
Hampton Inn Bennington
51 Hannaford Square Bennington VT
$139 nightly
The price is $151 total per night
$151 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.75 mi from city center
When you stay at Hampton Inn Bennington in Bennington, you'll be in the historical district, within a 5-minute drive of Bennington College and Bennington Potters Yard.
Pool
Breakfast included
The White House Inn
178 Route 9 East Wilmington VT
$184 nightly
The price is $202 total per night
$202 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
18.2 mi from city center
Located in Wilmington, The White House Inn is a 2-minute drive from Jim McGrath Gallery and Studio and 9 minutes from Jacksonville Pond.
The Porches Inn at Mass MoCA
231 River Street North Adams MA
$164 nightly
The price is $183 total per night
$183 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.41 mi from city center
In the heart of North Adams, The Porches Inn at Mass MoCA is within a 5-minute drive of Massachusetts Museum of Contemporary Art and Natural Bridge State Park.
Fairfield Inn & Suites by Marriott Williamstown
430 Main St Williamstown MA
$157 nightly
The price is $175 total per night
$175 total
Dec 16 - Dec 17
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.33 mi from city center
With a stay at Fairfield Inn & Suites by Marriott Williamstown in Williamstown, you'll be within a 10-minute walk of Colonial Plaza and Lower Linear Park.
Knotty Pine
130 Northside Dr Bennington VT
$110 nightly
The price is $120 total per night
$120 total
Dec 13 - Dec 14
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.02 mi from city center
With a stay at Knotty Pine in Bennington, you'll be steps from Green Mountain National Forest and a 1-minute drive from Bennington Dog Park.
Mountaineer Inn
270 Handle Rd West Dover VT
17.27 mi from city center
When you stay at Mountaineer Inn in West Dover, you'll be near ski lifts, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Best Western Bennington
220 Northside Drive Bennington VT
$106 nightly
The price is $115 total per night
$115 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
1.17 mi from city center
With a stay at Best Western Bennington in Bennington, you'll be steps from Green Mountain National Forest and a 2-minute drive from Bennington Dog Park.
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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Old Bennington hotels essential information
Accommodation | 997 hotels |
|---|---|
Lowest Price | $115 |
Highest Price | $271 |
Popular hotels | The Four Chimneys Inn, The Williams Inn, Mount Snow Grand Summit Resort, Hotel Downstreet, an Ascend Collection Hotel, Valley Craft Ales, Hampton Inn Bennington, The White House Inn, The Porches Inn at Mass MoCA, Fairfield Inn & Suites by Marriott Williamstown, Knotty Pine, Mountaineer Inn, Best Western Bennington |
Most Recent Old Bennington Hotel Reviews
Hotel Downstreet, an Ascend Collection Hotel
5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"Hot tub was relaxing. Parking was easy. Restaurant within walking distance. If you forget anything dollar general close."
A verified traveler stayed at Hotel Downstreet, an Ascend Collection Hotel
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