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$432 per night from 1 Sept to 2 Sept
AU$432
1 Sept - 2 Sept
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! (290 reviews)
"Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar"

Reviewed on 24 July 2026

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$231 per night from 1 Oct to 2 Oct
AU$231
1 Oct - 2 Oct
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
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$389 per night from 14 Sept to 15 Sept
AU$389
14 Sept - 15 Sept
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. ...
9.6/10 Exceptional! (663 reviews)
"Great place. Would love to have a swimming pool for lap swimming"

Reviewed on 31 Aug 2026

The Williams Inn
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.
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Shaftsbury VT
Stay at this family-friendly holiday home in Shaftsbury. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in their ...
10/10 Exceptional! (243 reviews)
"Beautiful private property near great shopping and restaurants. Really enjoyed spending time here host was very responsive. Look forward to coming back."

Reviewed on 30 Aug 2026

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing

Whitingham VT
Stay at this holiday home in Whitingham. Enjoy a garden, patios and an in-room coffee maker. Popular attractions Harriman Reservoir and Readsboro Community Library ...
9.8/10 Exceptional! (54 reviews)
"Our stay at this property was exactly what we needed. Not too quiet, not too loud. View of the water also gave us a sunrise each morning over the lake as well as a sunset behind the house that lit up the sky in beautiful colors. - Check in was very easy. The host was easy to contact and very fast ..."

Reviewed on 12 Aug 2026

Cozy Lakeside Tiny Home, kayaks included, fishing, hot tub, Near Skiing
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover VT
Stay at this condo in West Dover. Enjoy free Wi-Fi, patios and an in-room coffee maker. Popular attractions Mount Snow and Mount Snow Golf Course are located ...
9.2/10 Wonderful! (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"

Reviewed on 13 June 2026

Cozy 3 bedroom condo 2.5 miles to Mount Snow
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