Old Bennington, VT
Travel Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
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! (223 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
The price is ￥29,780 per night from Mar 11 to Mar 12
￥29,780
￥33,264 total
Mar 11 - Mar 12
includes taxes & 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! (573 reviews)
A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff.
Reviewed on Feb 7, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is ￥17,367 per night from Mar 17 to Mar 18
￥17,367
￥19,399 total
Mar 17 - Mar 18
includes taxes & 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! (1,001 reviews)
Spotless and front desk staff...friendly and accommodating
Reviewed on Feb 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.
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! (25 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
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington VT
Book a stay at this family-friendly vacation home in Wilmington. Enjoy free WiFi, a sauna, and a garden. Our guests praise the helpful staff in our reviews. ...
10/10 Exceptional! (208 reviews)
Tony was great at communicating.
Reviewed on Feb 8, 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 ...
6.4/10 (6 reviews)
The house was clean and well set up We had everything we needed and moreIt was a wonderful place to stay!
Reviewed on Oct 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.
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.
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.
