Old Bennington, VT
Travel Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
$212 nightly
The price is $232 total per night from Jan 12 to Jan 13
$232 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Book a stay at this golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (222 reviews)
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
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$124 nightly
The price is $138 total per night from Jan 27 to Jan 28
$138 total
Jan 27 - Jan 28, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,003 reviews)
Courteous staff
Reviewed on Dec 19, 2025
The Williams Inn
101 Spring Street Williamstown MA
$186 nightly
The price is $208 total per night from Jan 11 to Jan 12
$208 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (555 reviews)
Great staff, great rooms, we had a little issue with the door not opening, but they were quick to fix it. Bar staff, fantastic! Restaurant (we had brunch) delicious. This is our go to hotel when we stay in the Berkshires
Reviewed on Dec 28, 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.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Dover VT
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mount Snow and Heavy Metal Ski Lift ...
10/10 Exceptional! (12 reviews)
Wow. Just wow. That's all that needs to be said! Todd is an amazing host, and answered all of our questions promptly - often right away! And the house is simply spectacular. Spacious, luxurious, and right on the mountain! It was perfect for our large family of 16 and provided the most picturesque ...
Reviewed on Dec 28, 2025
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover VT
Book a stay at this ski condo in West Dover. Enjoy a fitness center, tennis courts, and ski-in/ski-out access. Popular attractions Mount Snow and Seasons Ski ...
8.2/10 Very Good! (23 reviews)
Great place with great amenities!
Reviewed on Nov 18, 2025
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Dover VT
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mount Snow and Heavy Metal Ski Lift ...
9.8/10 Exceptional! (49 reviews)
The place is very close to the slopes, which is a big plus. The three bedroom with three bathrooms were more than enough for 3 families. The kitchen had everything we needed. There were games for kids. The only negative was that the toilet in one of the bathrooms was not flushing. I tried to reach ...
Reviewed on Dec 26, 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.
Popular places to visit
Bennington Battle Monument
Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Old First Congregational Church
Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.
Prospect Mountain Cross-Country Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.
Prospect Mountain Nordic Ski Center
Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and coffeehouses.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.
Robert Frost Stone House Museum
You can spend an afternoon exploring the galleries in Robert Frost Stone House Museum during your trip to Bennington. Discover the area's charming coffeehouses and its fascinating museums.
Things to do
Vermont RT 100 Self Guided Driving Audio Tour
$17
per traveler
- Bennington Battle Monument
- Bennington Museum
- Old First Congregational Church
- Mount Snow
- Massachusetts Museum of Contemporary Art
- Williams College
- Green Mountain National Forest
- Mount Snow Golf Course
- The Clark Art Institute
- Mount Greylock
- Prospect Mountain Cross-Country Ski Center
- Mount Equinox
- Prospect Mountain Nordic Ski Center
- Bennington College
- Willard Mountain
- Williamstown Theatre Festival
- Sugar Shack
- Battenkill River
- Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
- Sterling and Francine Clark Art Institute
- Lake Shaftsbury State Park
- Williams College Museum of Art
- The Hermitage Golf Club
- Grafton Lakes State Park
- Natural Bridge State Park
- Grand Summit Express Ski Lift
- Harriman Reservoir
- Pineridge Cross Country Ski Center
- Deerfield River
- Brodie Mountain
- Robert Frost Stone House Museum
