Old Bennington Travel Guide
Tourist Guide
Visit Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
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 ...
9.6/10 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 12 Jan 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is Rp3.359.916 per night from 11 Mar to 12 Mar
Rp3.359.916
Rp3.753.026 total
11 Mar - 12 Mar
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! (575 reviews)
Absolutely wonderful!
Reviewed on 16 Feb 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is Rp1.924.607 per night from 22 Mar to 23 Mar
Rp1.924.607
Rp2.149.785 total
22 Mar - 23 Mar
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! (1,001 reviews)
Spotless and front desk staff...friendly and accommodating
Reviewed on 11 Feb 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.
Bennington Gem w/ Smart TV Near Historic District!
Bennington VT
Stay at this business-friendly cottage in Bennington. Enjoy free parking. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display ...
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
Breathtaking Mtn Views: Stylish Rustic Retreat!
Bennington VT
Stay at this cottage in Bennington. Enjoy free parking, an in-room coffee maker and air conditioning. Popular attractions Bennington Center for the Arts and ...
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 ...
8.4/10 Very Good! (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.
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 cafes.
Prospect Mountain Cross-Country Ski Center
4/5(1 review)
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
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.
Things to do
Vermont RT 100 Self Guided Driving Audio Tour
Rp285.772
per traveller
