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 CA $524 per night from Sep 9 to Sep 10
CA $524
CA $571 total
Sep 9 - Sep 10
includes taxes & fees
Book a stay at this golf B&B in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (291 reviews)
"Very nice, quiet place. Relaxing and cute."

Reviewed on Sep 7, 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 CA $198 per night from Sep 29 to Sep 30
CA $198
CA $221 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,004 reviews)
"Nice and conveniently located"

Reviewed on Sep 7, 2026

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is CA $258 per night from Sep 21 to Sep 22
CA $258
CA $288 total
Sep 21 - Sep 22
includes taxes & fees
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
The Williams Inn
See all 1,010 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
Book a stay at this family-friendly vacation home in Shaftsbury. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition ...
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 Aug 30, 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 vacation home in Whitingham. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Harriman Reservoir and Readsboro Community ...
9.8/10 Exceptional! (55 reviews)
"Really enjoyed our peaceful stay. Perfect for us a couple!"

Reviewed on Aug 25, 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 WiFi, patios, and an in-room coffeemaker. 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 Jun 13, 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 coffeehouses 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

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