Old Bennington Travel Guide

Tourist 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 showing 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! (218 reviews)
"Nice and cozy"

Reviewed on 13 Jul. 2025

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The Four Chimneys Inn
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is AU$406 per night from 10 Aug to 11 Aug
AU$406
10 Aug - 11 Aug
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! (469 reviews)
"Hrwat"

Reviewed on 11 Jul. 2025

The Williams Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
The price is AU$276 per night from 17 Aug to 18 Aug
AU$276
17 Aug - 18 Aug
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! (1,001 reviews)
"Great place"

Reviewed on 16 Jul. 2025

Hotel Downstreet, Ascend Hotel Collection
See all 948 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.
Charming Berkshires Retreat – Minutes to Williamstown

Charming Berkshires Retreat – Minutes to Williamstown

Williamstown
Stay at this vacation home in Williamstown. Enjoy laundry facilities and an in-room coffeemaker. Popular attractions Green River Wildlife Management Area and ...
Weekend Stop Before Camp
"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… ..."

Reviewed on 24 Jun. 2025

Charming Berkshires Retreat – Minutes to Williamstown
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! (3 reviews)
Special house
"Excellent house. Privacy for five adults . Two couples one single. All features new and first rate.- sheets, towels, kitchen equipment etc. unique design by architect."

Reviewed on 28 Jun. 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

Activities

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

AU$26
per traveller
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Old Bennington