Old Bennington Travel Guide
Tourist Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is ฿8,229 per night from 19 May to 20 May
฿8,229
฿8,969 total
19 May - 20 May
includes taxes & fees
Stay at this golf B&B in Bennington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.4/10 Exceptional! (283 reviews)
Peaceful and whimsical stay in a historic inn. The breakfast was delicious (served with the best local maple syrup) and location was a 5 minute drive to the downtown area.
Reviewed on 19 Apr 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is ฿4,883 per night from 18 May to 19 May
฿4,883
฿5,454 total
18 May - 19 May
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,009 reviews)
Clean room...
Reviewed on 12 May 2026
The Williams Inn
101 Spring Street Williamstown MA
The price is ฿9,557 per night from 14 May to 15 May
฿9,557
฿10,675 total
14 May - 15 May
includes taxes & fees
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
9.6/10 Exceptional! (625 reviews)
Staff was very helpful. Rooms were great. Unbeatable location for Williamstown (especially if you’re in town for an athletic event at Williams). Really solid breakfast with friendly and attentive wait staff. Only minor complaint is that the WiFi is not great. Other than that it was a perfect ...
Reviewed on 10 May 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.
Two Brooks Lodge
1054 Sawmill Rd Bennington VT
Stay at this holiday home in Bennington. Enjoy free Wi-Fi, free parking and laundry facilities. Popular attractions Robert Frost Stone House Museum and Norman ...
4.8/10 (3 reviews)
Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in ...
Reviewed on 20 Apr 2023
< 1 Mi to Historic District! Retreat in Bennington
Bennington VT
Stay at this business-friendly cottage in Bennington. Enjoy free parking and air conditioning. Popular attractions Hemmings Motor News Car Lover's Convenience ...
8/10 Very Good! (2 reviews)
Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 ...
Reviewed on 21 Oct 2025
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd Stratton VT
Stay at this ski aparthotel in Stratton. Enjoy free Wi-Fi, free parking and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager Ski Lift ...
8.6/10 Excellent! (83 reviews)
Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained
Reviewed on 31 Jan 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(3 reviews)
Learn about the local history of Old Bennington with a stop at Bennington Battle Monument. In the area, take in the art scene and mountain views.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
You can spend an afternoon exploring the galleries in Hemmings Motor News Car Lover's Convenience Store & Vehicle Display during your travels in Bennington. While you're here, you can savour the cosy cafes.
Bennington Museum
You can spend an afternoon exploring the galleries in Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and cafes.
Woodford State Park
You can take time to visit Woodford State Park during your travels to Woodford.
Bennington Center for the Arts
Enjoy an outing to Bennington Center for the Arts during your stay in Bennington. Experience the area's art scene and museums.
Southern Vermont College
Explore the campus of Southern Vermont College during your travels in Bennington. While you're here, you can savour the cosy cafes.
Things to do
Vermont RT 100 App-Guided Driving Audio Tour
฿542
per traveller
