Old Bennington Travel Guide
Tourist Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
The price is 6.724.287 ₫ per night from 10 Jun to 11 Jun
6.724.287 ₫
7.329.472 ₫ total
10 Jun - 11 Jun
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! (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 26 May 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is 4.287.102 ₫ per night from 8 Jun to 9 Jun
4.287.102 ₫
4.788.692 ₫ total
8 Jun - 9 Jun
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,002 reviews)
"Check in was simple and quick. Staff was courteous and helpful. The room was clean and spacious. We had a pleasant stay and checkout was simple."
Reviewed on 1 Jun 2026
The Williams Inn
101 Spring Street Williamstown MA
The price is 8.658.951 ₫ per night from 15 Jun to 16 Jun
8.658.951 ₫
9.672.048 ₫ total
15 Jun - 16 Jun
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! (631 reviews)
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."
Reviewed on 30 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 Norman Rockwell Exhibition and Robert Frost ...
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
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.
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.
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.
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.
Old First Congregational Church
Find out about the history of Old Bennington when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.
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.
- Bennington Battle Monument
- Old First Congregational Church
- Mount Snow
- Green Mountain National Forest
- Williams College
- Mount Greylock
- Battenkill River
- Harriman Reservoir
- Waubeeka Golf Links
- Lake Shaftsbury State Park
- Natural Bridge State Park
- Taconic Golf Club
- Windsor Lake Park
- Bennington College
- Sugar Shack
- The Hermitage Club
- Bennington Center for the Arts
- Deerfield River
- Bennington Battlefield Historic Site
