Old Bennington Travel Guide

Tourist Guide

A statue with outstretched arms and a tall obelisk in the background.
A tall stone monument with a central entrance, surrounded by a well-maintained lawn and trees.
A white historic building with arched windows and a stone fence with headstones.
A lush green landscape with a prominent hill in the background, surrounded by dense forests and scattered houses.
A tall stone obelisk with a weather vane on top, set against a cloudy sky.
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
The price is AU$370 per night from 1 Nov to 2 Nov
AU$370
1 Nov - 2 Nov
includes taxes & fees
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 ...
9.4/10 Exceptional! (291 reviews)
"Very nice, quiet place. Relaxing and cute."

Reviewed on 7 Sept 2026

The Four Chimneys Inn
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is AU$325 per night from 9 Nov to 10 Nov
AU$325
9 Nov - 10 Nov
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. ...
The Williams Inn
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
The price is AU$271 per night from 19 Oct to 20 Oct
AU$271
19 Oct - 20 Oct
includes taxes & fees
Stay at this spa resort in West Dover. Enjoy free Wi-Fi, a full-service spa and a free local area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
Grand Summit Resort, A Vail Resorts Property
See all 1,007 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.
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 VT
Stay at this family-friendly apartment in Pownal. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Solomon Wright Library and Solomon Wright ...
9.2/10 Wonderful! (92 reviews)
"We had a lovely stay at this property. We stayed in the lower apartment and check in was easy. The online instructions aren't the most up to date, but the hosts were very responsive and easy to get a hold of. Loved the smores kit and fire pit being fully stocked as well as the instant coffee provided. ..."

Reviewed on 13 Oct 2026

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Seasons On Mount Snow - Ski-in/Ski-out

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

Dover VT
Stay at this ski condo in West Dover. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Mount Snow and Seasons Ski Lift are located ...
9.8/10 Exceptional! (204 reviews)
"Great experience! Thank you!"

Reviewed on 11 Oct 2026

Seasons On Mount Snow - Ski-in/Ski-out
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
Stay at this ski holiday home in West Dover. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mount Snow and Heavy Metal Ski Lift are located ...
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
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.

Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.
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Activities

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

AU$24
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington