Book Hotels in Old Bennington, VT
Cabins, apartments, houseboats! We offer comfortable & private vacation rentals
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Old Bennington hotels

The Four Chimneys Inn
21 West Road Bennington VT
$249 nightly
The price is $271 total per night from Feb 4 to Feb 5
$271 total
Feb 4 - Feb 5
Total with taxes and fees
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
$186 nightly
The price is $208 total per night from Jan 25 to Jan 26
$208 total
Jan 25 - Jan 26
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 ...
General ambience is lovely.
Reviewed on Jan 8, 2026

The Porches Inn at Mass MoCA
231 River Street North Adams MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $211 total per night from Jan 19 to Jan 20
$211 total
Jan 19 - Jan 20
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 ...
Wow. This hotel is such a great find. Not only is it clean and unique, the rooms are large and the staff are super helpful and nice. Breakfast was nice. The pool was slightly colder than I expected but it was 5 degrees outside and windy so its understandable. The hot tub was very comfortable. I would ...
Reviewed on Jan 2, 2026

The White House Inn
178 Route 9 East Wilmington VT
$184 nightly
The price is $202 total per night from Jan 19 to Jan 20
$202 total
Jan 19 - Jan 20
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
Amazing hotel with an excellent restaurant attached. My suite was like a good sized apartment. Definitely staying there again.
Reviewed on Jan 9, 2026

Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
$125 nightly
The price is $140 total per night from Feb 2 to Feb 3
$140 total
Feb 2 - Feb 3
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 ...
Staff were good and the room was clean. Bed is comfortable and room is fairly large. Couch is uncomfortable for prolonged sitting. Not having a cafe/restaurant open Tuesdays and Wednesdays or any breakfast bar is a bit inconvenient but there are other local options. Site location makes for some traffic ...
Reviewed on Jan 8, 2026

Mount Snow Grand Summit Resort
89 Grand Summit Way West Dover VT
$336 nightly
The price is $369 total per night from Feb 2 to Feb 3
$369 total
Feb 2 - Feb 3
Total with taxes and fees
Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi ...
Ski on skis off fantastic. Ski valet right on it
Reviewed on Jan 11, 2026

Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $164 total per night from Jan 18 to Jan 19
$164 total
Jan 18 - Jan 19
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like on-the-go breakfast and ...
Pet friendly, cooking was great plus, warm room
Reviewed on Jan 5, 2026

Hampton Inn Bennington
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $142 total per night from Feb 1 to Feb 2
$142 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. ...
Good Beautiful stay
Reviewed on Jan 10, 2026

Valley Craft Ales
18 N Main St Wilmington VT
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $168 total per night from Jan 26 to Jan 27
$168 total
Jan 26 - Jan 27
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 ...
Clean simple room over the brewery was convenient for dinner and relaxing after. Being right on the main road wasn't loud, but made it a little difficult to get in and out of with traffic, especially with slightly slippery conditions.
Reviewed on Jan 11, 2026
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
"Ski on skis off fantastic. Ski valet right on it "
A verified traveler stayed at Mount Snow Grand Summit Resort
Explore More Ways to Travel with Travelocity
- Hotels near Lake Shaftsbury State Park
- Southern Vermont Hotels
- Hotels near Sugar Shack
- Cheap Hotels in Woodford
- Inns in Woodford
- Sandgate Hotels
- Hotels near Green Mountain National Forest
- Whitingham Hotels
- 4 Star Hotels in Bennington
- 5 Star Hotels in Bennington
- Apartments in Bennington
- B&B in Bennington
- Cabins in Bennington
- Condos in Bennington
- Cottages in Bennington
- Adults Only Resorts & in Bennington
- Boutique Hotels in Bennington
- Cheap Hotels in Bennington
- Convention Center Hotels in Bennington
- Hotels with Suites in Bennington
- Hotels with Balconies in Bennington
- Hotels with Bar in Bennington
- Hotels with Free Parking in Bennington
- Hotels with Hot Tubs in Bennington
- Hotels with an Indoor Pool in Bennington
- Hotels with Kitchenettes in Bennington
- Luxury Hotels in Bennington
- Pet Friendly Hotels in Bennington
- Romantic Getaways & Hotels in Bennington
- Ski Resorts and in Bennington
- Spa Resorts & in Bennington
- Bennington Hotels
- Inns in Bennington
- Lodges in Bennington
- Motels in Bennington
- Vacation Homes in Bennington
- Resorts in Bennington
- West Arlington Hotels
- Hotels near Bennington College
- B&B in Pownal
- Cabins in Pownal
- Cottages in Pownal
- Pet Friendly Hotels in Pownal
- Pownal Hotels
- Motels in Pownal
- Vacation Homes in Pownal
- Hotels near Norman Rockwell Exhibition
- Hotels near The Hermitage Golf Club
- Hotels near Fiddlehead at Four Corners
- Cabins in Stamford
- Chalets in Stamford
- Cottages in Stamford
- Extended Stay Hotels in Stamford
- Stamford Hotels
- Motels in Stamford
- Hotels near Park McCullough House
- Mount Snow Valley Hotels
- Hotels near Mount Snow Golf Course
- Arlington Hotels
- Glastenbury Hotels
- Hotels near Mount Snow
- Hotels near Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
- Wilmington Hotels
- B&B in Bennington County
- Condos in Bennington County
- Pet Friendly Hotels in Bennington County
- B&B in Shaftsbury
- Cabins in Shaftsbury
- Chalets in Shaftsbury
- Cottages in Shaftsbury
- Shaftsbury Hotels
- Hotels near Prospect Mountain Nordic Ski Center
- 5 Star Hotels in North Bennington
- Apartments in North Bennington
- B&B in North Bennington
- Cabins in North Bennington
- Condos in North Bennington
- Extended Stay Hotels in North Bennington
- Guest Houses in North Bennington
- Ski Resorts and in North Bennington
- North Bennington Hotels
- Inns in North Bennington
- Rv Parks in North Bennington
- Resorts in North Bennington
- Villas in North Bennington
- Hotels near Howard Park
- Ski Resorts and in North Bennington Historic District
- North Bennington Historic District Hotels
- Somerset Hotels
- Inns in Somerset
- Lodges in Somerset
- Resorts in Somerset
- Hotels near Mount Equinox
- Hotels near Robert Frost Stone House Museum






