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! (222 reviews)
"This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was ..."

Reviewed on 2 Sept 2025

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The Four Chimneys Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is €126 per night from 13 Nov to 14 Nov
€126
13 Nov - 14 Nov
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! (1,003 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"

Reviewed on 9 Oct 2025

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is €204 per night from 2 Nov to 3 Nov
€204
2 Nov - 3 Nov
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! (520 reviews)
"Lovely clean room with a fabulous shower. Tea/coffee available 24 hours with a choice of milks which is great. Refillable glass bottle in the room to collect fresh water which meant no plastic bottles. Plenty of parking, cosy lobby and restaurant food excellent."

Reviewed on 10 Oct 2025

The Williams Inn
See all 974 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.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Sunderland
Stay at this vacation home in Arlington. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Mount Equinox and Hildene are located ...
10/10 Exceptional! (121 reviews)
"This home was one of the most spectacular that I have rented. We were sorry to not have stayed longer! The view from this home was awe inspiring! We enjoyed the hot tub and well appointed deck to soak in this panoramic view of the forested mountain side. If you had kids along there even was a grassy ..."

Reviewed on 14 Oct 2025

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Wilmington
Book a stay at this ski chalet in Wilmington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Mount Snow and The Hermitage Golf Club are ...
9.2/10 Wonderful! (40 reviews)
"My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay ..."

Reviewed on 17 Aug 2025

Beautiful Lodging at Mount Snow with Hot Tub on Deck
Fabulous, Beautifully Appointed Luxury 5 Bedroom Ski-Home Steps from Mount Snow

Fabulous, Beautifully Appointed Luxury 5 Bedroom Ski-Home Steps from Mount Snow

Dover, VT
Stay at this condo in West Dover. Enjoy laundry facilities and air conditioning. Popular attractions Mount Snow and Snow Lake are located nearby.
Fabulous, Beautifully Appointed Luxury 5 Bedroom Ski-Home Steps from Mount Snow
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

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.

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

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.

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