Old Bennington, VT
Travel Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
$235 nightly
The price is $256 total per night from May 27 to May 28
$256 total
May 27 - May 28
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 ...
9.4/10 Exceptional! (284 reviews)
"Had a great experience here. The staff was friendly and helpful. Chatting with the bartender and other guests at the bar over a nightcap made for an enjoyable evening. The room was clean and comfortable and the breakfast was fantastic."
Reviewed on May 26, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$152 nightly
The price is $170 total per night from Jun 2 to Jun 3
$170 total
Jun 2 - Jun 3
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 ...
8.8/10 Excellent! (1,004 reviews)
"Room was newly completed and fresh."
Reviewed on May 25, 2026
The Williams Inn
101 Spring Street Williamstown MA
$258 nightly
The price is $288 total per night from May 27 to May 28
$288 total
May 27 - May 28
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! (628 reviews)
"Great property and restaurant. Perfect location and very helpful, friendly staff."
Reviewed on May 23, 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.
Seasons On Mount Snow - Ski-in/Ski-out
Dover VT
Book a stay at this ski condo in West Dover. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mount Snow and Seasons Ski Lift are ...
9.8/10 Exceptional! (188 reviews)
"Good location. Nice 2 Bedroom space"
Reviewed on Apr 9, 2026
Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown
Williamstown MA
Stay at this vacation home in Williamstown. Enjoy air conditioning. Popular attractions Buxton Gardens and Farm Museum are located nearby.
9.8/10 Exceptional! (7 reviews)
"This place is great if you like a beautiful view and don’t like neighbors. So quiet, and peaceful. The house is cozy and although we stayed for a work trip it felt like a vacation when I woke up to a beautiful sunrise over the mountains."
Reviewed on May 15, 2026
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Pownal VT
Book a stay at this family-friendly apartment in Pownal. Enjoy free WiFi, private pools, and a garden. Popular attractions Solomon Wright Library and Solomon ...
9.4/10 Exceptional! (86 reviews)
"The rental was adequate but the kitchen was older, despite the cabinets being painted and the hardware being replaced. The appliances need replacing, including the coffee pot, and the seal around the kitchen sink had mildew, which made cooking unappealing. The hot tub was a nice addition, however, ..."
Reviewed on Dec 10, 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
4.5/5(72 reviews)
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the coffeehouses and its art scene while you're in the area.
Bennington Museum
4.5/5(11 reviews)
You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.
Southern Vermont College
4.5/5(7 reviews)
Explore the campus of Southern Vermont College, during your travels in Bennington. While you're here, you can savor the charming coffeehouses.
Prospect Mountain Cross-Country Ski Center
4.5/5(11 reviews)
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.
Woodford State Park
You can take time to visit Woodford State Park during your travels to Woodford.
Bennington Center for the Arts
5/5(3 reviews)
Enjoy an outing to Bennington Center for the Arts during your stay in Bennington. Experience the area's art scene and museums.
Things to do
Vermont RT 100 App-Guided Driving Audio Tour
$17
per traveler
- Bennington Museum
- Bennington Battle Monument
- Old First Congregational Church
- Mount Snow
- Green Mountain National Forest
- Massachusetts Museum of Contemporary Art
- Williams College
- Mount Greylock
- The Clark Art Institute
- Mount Snow Golf Course
- Mount Equinox
- Grafton Lakes State Park
- Battenkill River
- Lake Shaftsbury State Park
- Waubeeka Golf Links
- Williamstown Theatre Festival
- Bennington College
- Harriman Reservoir
- Sugar Shack
- Taconic Golf Club
- Natural Bridge State Park
- Bennington Center for the Arts
- Deerfield River
- Windsor Lake Park
- North Branch Deerfield River
- Southern Vermont College
- Western Gateway Heritage State Park
- Adams Theater
- Prospect Mountain Cross-Country Ski Center
- The Hermitage Golf Club
