Old Bennington, VT

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
$249 nightly
The price is $271 total per night from Nov 1 to Nov 2
$271 total
Nov 1 - Nov 2
Total with taxes and 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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundable
$206 nightly
The price is $230 total per night from Nov 10 to Nov 11
$230 total
Nov 10 - Nov 11
Total with taxes and 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
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
$168 nightly
The price is $184 total per night from Nov 16 to Nov 17
$184 total
Nov 16 - Nov 17
Total with taxes and fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free 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
Book a stay at this family-friendly apartment in Pownal. Enjoy free WiFi, private pools, and a garden. Popular attractions Solomon Wright Library and Solomon ...
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 Oct 13, 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
Book a stay at this ski condo in West Dover. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Mount Snow and Seasons Ski Lift are ...
9.8/10 Exceptional! (204 reviews)
"Great experience! Thank you!"

Reviewed on Oct 11, 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
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mount Snow and Heavy Metal Ski Lift ...
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 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

$17
per traveler
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington

Cities near Old Bennington

A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington