Old Bennington, VT
Travel Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
$227 nightly
The price is $248 total per night from Mar 5 to Mar 6
$248 total
Mar 5 - Mar 6
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! (281 reviews)
This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again.
Reviewed on Jan 12, 2026
The Williams Inn
101 Spring Street Williamstown MA
$181 nightly
The price is $203 total per night from Feb 22 to Feb 23
$203 total
Feb 22 - Feb 23
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! (577 reviews)
Elegant and oupdated decor throughout, spotlessly clean Welocation,
Reviewed on Feb 21, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$114 nightly
The price is $127 total per night from Mar 22 to Mar 23
$127 total
Mar 22 - Mar 23
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! (1,003 reviews)
Room was clean and the staff are always efficient and courteous. Location is convenient for our purposes.
Reviewed on Feb 20, 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.
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 ...
8.6/10 Excellent! (35 reviews)
The local Vacasa team is very responsive.The accommodations are ok but the location can't be beat.There is an endless supply of firewood to have a fire, which was really nice. The ski locker outside makes it easy to get on and off the slopes.To get to the slopes, you walk out the front door to the ...
Reviewed on Feb 13, 2026
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
Wilmington VT
Stay at this cabin in Wilmington. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Mount Snow and The Hermitage Golf Club are located ...
7.6/10 Good! (9 reviews)
Home was clean, plenty of room. Check in information was vague. Would have liked to have more information about the pool. We ended up going and not bringing towels since details about the amenities were sparse.
Reviewed on Feb 1, 2026
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Readsboro VT
Book a stay at this family-friendly vacation home in Readsboro. Enjoy a garden, laundry facilities, and patios. Popular attractions Readsboro Community Library ...
10/10 Exceptional! (9 reviews)
The place was in great shape - everything was as pictured online. Just beautiful. It was historically cold while we were there so we did not get to explore outside much, but even in 0 degree temps the hot tub was welcoming (with winter hats on!), and the wood stove was amazing and kept it very cozy ...
Reviewed on Feb 14, 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.
Popular places to visit
Bennington Battle Monument
4.5/5(71 reviews)
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.
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.
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.
Old First Congregational Church
5/5(4 reviews)
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.
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.
Things to do
Vermont RT 100 Self Guided Driving Audio Tour
$17
per traveler
- Bennington Battle Monument
- Old First Congregational Church
- Bennington Museum
- Mount Snow
- Williams College
- Green Mountain National Forest
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- The Clark Art Institute
- Mount Snow Golf Course
- Mount Equinox
- Bennington College
- Prospect Mountain Nordic Ski Center
- Prospect Mountain Cross-Country Ski Center
- Lake Shaftsbury State Park
- Willard Mountain
- Battenkill River
- The Hermitage Golf Club
- Williamstown Theatre Festival
- Deerfield River
- Natural Bridge State Park
- Bennington Battlefield Historic Site
- Grand Summit Express Ski Lift
- Sterling and Francine Clark Art Institute
- Sugar Shack
- Harriman Reservoir
- Grafton Lakes State Park
- Western Gateway Heritage State Park
- Taconic Golf Club
- Southern Vermont College