Book Hotels in Old Bennington, VT
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Top Old Bennington hotels

The Four Chimneys Inn
21 West Road, Bennington, VT
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi ...
"This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was ..."
Reviewed on Sep 2, 2025

The Williams Inn
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
$223 nightly
The price is $250 total per night from Oct 29 to Oct 30
$250 total
Oct 29 - Oct 30
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference ...
"Very helpful and friendly front desk staff. The room was lovely!"
Reviewed on Sep 25, 2025

The Porches Inn at Mass MoCA
231 River Street, North Adams, MA
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $256 total per night from Sep 30 to Oct 1
$256 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the ...
"True to its historic character, the attention to detail was splendid!"
Reviewed on Sep 24, 2025

Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $162 total per night from Oct 28 to Oct 29
$162 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express ...
a gem
"Totally perfect for mass mocha"
Reviewed on Sep 21, 2025

Mountaineer Inn
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Sep 30 to Oct 1
$127 total
Sep 30 - Oct 1
Total with taxes and fees
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are ...
"There was no staff on duty and the carpet in the room was not vacuumed and there was no ice machine"
Reviewed on Sep 23, 2025

Mount Snow Grand Summit Resort
89 Grand Summit Way, West Dover, VT
Fully refundable
$153 nightly
The price is $168 total per night from Oct 30 to Oct 31
$168 total
Oct 30 - Oct 31
Total with taxes and fees
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free ...
"Great place to stay!"
Reviewed on Sep 25, 2025

Valley Craft Ales
18 N Main St, Wilmington, VT
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Oct 27 to Oct 28
$97 total
Oct 27 - Oct 28
Total with taxes and fees
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a communal living room are also ...
"Very clean and comfortable room with an excellent view of the stream and the trees outside. No TV in the room; perfect for anyone looking for a night away. The walls are thin so if you are sensitive to noise I would not recommend as I could clearly hear my neighbor snoring, however ear plugs are ..."
Reviewed on Sep 25, 2025

Best Western Bennington
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Oct 19 to Oct 20
$133 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. ...
"Great stay"
Reviewed on Sep 23, 2025

Howard Johnson by Wyndham Williamstown
213 Main St, Williamstown, MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Sep 30 to Oct 1
$123 total
Sep 30 - Oct 1
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the ...
"Clean room!"
Reviewed on Sep 7, 2025
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
Recent Old Bennington hotel reviews by fellow wanderers

Mount Snow Grand Summit Resort
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Great place to stay!"
A verified traveler stayed at Mount Snow Grand Summit Resort
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