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.
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 CA $222 per night from Nov 9 to Nov 10
CA $222
per night
Nov 9 - Nov 10
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
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 $167 per night from Nov 18 to Nov 19
CA $167
per night
Nov 18 - Nov 19
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 ...
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 $283 per night from Nov 8 to Nov 9
CA $283
per night
Nov 8 - Nov 9
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 993 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! (205 reviews)
"Great location, beautiful surroundings. Our kids loved the fun games and Nintendo!"

Reviewed on Oct 19, 2026

Seasons On Mount Snow - Ski-in/Ski-out
Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia

Dover VT
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, laundry facilities, and ski-in/ski-out access. Popular attractions Mount Snow and Heavy ...
10/10 Exceptional! (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"

Reviewed on Mar 10, 2026

Modern Mount Snow Gnarvana - Steps to Carinthia
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.
See properties

Things to do

Vermont RT 100 App-Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
80% of travellers recommend
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington