Old Bennington

Travel Guide

Bennington Battle Monument which includes landscape views
Bennington Battle Monument which includes a monument and heritage elements
Bennington Battle Monument featuring landscape views and a small town or village
Bennington Battle Monument featuring landscape views
Old Bennington
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road, Bennington, VT
Stay at this 4-star 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! (219 reviews)
Perfection!!
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite."

Reviewed on 20 Aug 2025

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The Four Chimneys Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
The price is €137 per night from 23 Sept to 24 Sept
€137
23 Sept - 24 Sept
includes taxes & fees
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,002 reviews)
"Staff were wonderful. Bethany at the front desk was friendly and helpful!Very clean. Have stayed here numerous times and always have fun. It’s a good area with cute shops."

Reviewed on 22 Aug 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is €222 per night from 7 Sept to 8 Sept
€222
7 Sept - 8 Sept
includes taxes & fees
Stay at this 4-star 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! (488 reviews)
"Wonderful stay in Williamstown!"

Reviewed on 22 Aug 2025

The Williams Inn
See all 951 properties in Old Bennington
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.
Park Street Penthouse Apartment

Park Street Penthouse Apartment

Adams
Stay at this apartment in Adams. Enjoy laundry facilities and air conditioning. Popular attractions Adams Theater and Berkshire Scenic Railway Museum are located ...
9.4/10 Exceptional! (9 reviews)
"This apartment is a very interesting space! Big beautiful wooden floors, fit for a dance class! The bones of the apartment are so beautiful. The bed in the bedroom was very comfortable. The single bed in the main space, albeit wide open, was also quite beautiful and comfortable. Bare bones decoration ..."

Reviewed on 11 Aug 2025

Park Street Penthouse Apartment
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Pownal
Book a stay at this family-friendly apartment in Pownal. Enjoy free WiFi, private pools, and a garden. Popular attractions Solomon Wright Library and Solomon ...
9.2/10 Wonderful! (46 reviews)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub!"

Reviewed on 11 Jun 2025

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
Stay at this vacation home in Williamstown. Enjoy a garden, laundry facilities, and patios. Popular attractions Williams College Taconic Golf Course and Lunder ...
10/10 Exceptional! (4 reviews)
"We thoroughly enjoyed our stay at this exceptional property. We felt we had walked into the pages of Architectural Digest! The house was so beautiful, and so well appointed - the perfect place for our small family gathering. The hosts responded quickly to the few questions that we had, and the whole ..."

Reviewed on 22 Jul 2025

Contemporary Berkshire Home with Views of Taconic Golf Course
See all properties in Old Bennington
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 which includes landscape views

Bennington Battle Monument

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.

Bennington Battle Monument
Old First Congregational Church

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.

Old First Congregational Church

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.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

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.

Prospect Mountain Cross-Country Ski Center

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.

Bennington Museum

Bennington Potters Yard

You can do some window-shopping at Bennington Potters Yard during your trip to Bennington. Discover the cafes and its art scene while you're in the area.

Bennington Potters Yard
Bennington Battle Monument which includes landscape views

Bennington