Old Bennington

Travel 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 HK$1,856 per night from 1 Nov to 2 Nov
HK$1,856
HK$2,023 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
Fully refundable
The price is HK$1,594 per night from 8 Nov to 9 Nov
HK$1,594
HK$1,781 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 HK$1,177 per night from 10 Nov to 11 Nov
HK$1,177
HK$1,408 total
10 Nov - 11 Nov
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 ...
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! (203 reviews)
"We had an amazing stay at this Seasons condo. The condo was clean and spacious. The pool and fitness center was newly updated and a great indoor activity. The area was beautiful and close to all the attractions."

Reviewed on 21 Sept 2026

Seasons On Mount Snow - Ski-in/Ski-out
Crafts Inn, Hotel Suite with pool and hot tub.

Crafts Inn, Hotel Suite with pool and hot tub.

Wilmington VT
Stay at this aparthotel in Wilmington. Enjoy free Wi-Fi, a sauna and a garden. Popular attractions South Main Street and Jim McGrath Gallery and Studio are located ...
8.6/10 Excellent! (7 reviews)
"Great location. The room was very clean and we enjoyed the hot tub."

Reviewed on 20 Sept 2026

Crafts Inn, Hotel Suite with pool and hot tub.
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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Things to do

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

HK$133
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington