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! (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
The price is AU$247 per night from 27 Oct to 28 Oct
AU$247
27 Oct - 28 Oct
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! (1,011 reviews)
a gem
"Totally perfect for mass mocha"

Reviewed on 21 Sept 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 AU$381 per night from 29 Oct to 30 Oct
AU$381
29 Oct - 30 Oct
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! (506 reviews)
"Great hotel. Food and drinks were very good. Not much to do in the town but a great place for walking."

Reviewed on 21 Sept 2025

The Williams Inn
See all 969 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.
Seasons On Mount Snow - Ski-in/Ski-out

Seasons On Mount Snow - Ski-in/Ski-out

Dover
Book a stay at this ski condo in West Dover. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mount Snow and Seasons Ski Lift are ...
9.6/10 Exceptional! (163 reviews)
"Awesome place. Great host."

Reviewed on 2 Sept 2025

Seasons On Mount Snow - Ski-in/Ski-out
Studio style farm stay

Studio style farm stay

North bennington
Stay at this apartment in North Bennington. Enjoy free WiFi, a pool table, and patios. Popular attractions Park McCullough House and Robert Frost Stone House ...
8.8/10 Excellent! (32 reviews)
Rustic weekend
"Simple"

Reviewed on 7 July 2025

Studio style farm stay
Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT

Arlington
Stay at this apartment in Arlington. Enjoy free WiFi, laundry facilities, and cable/satellite TV service. Popular attractions Norman Rockwell Exhibition and ...
9.8/10 Exceptional! (51 reviews)
"Great place—though it’s a basement, it’s nearly perfect. We’d definitely stay here again"

Reviewed on 15 Sept 2025

Spacious apartment in beautiful, historic Arlington VT
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