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 Rp4.243.234 per night from 1 Nov to 2 Nov
Rp4.243.234
Rp4.625.125 total
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 Rp3.644.105 per night from 8 Nov to 9 Nov
Rp3.644.105
Rp4.070.465 total
8 Nov - 9 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 Rp2.825.626 per night from 20 Oct to 21 Oct
Rp2.825.626
Rp3.381.747 total
20 Oct - 21 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.
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Stay at this ski aparthotel in Stratton. Enjoy free Wi-Fi, free parking and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager Ski Lift ...
8.6/10 Excellent! (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."

Reviewed on 11 Oct 2026

Long Trail House at Stratton Mountain Resort
See all 816 properties in 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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Things to do

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

Rp298.124
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington