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
The price is ₩514,940 per night from Sep 9 to Sep 10
₩514,940
₩561,285 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! (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 Jul 24, 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 ₩194,537 per night from Sep 27 to Sep 28
₩194,537
₩217,298 total
Sep 27 - Sep 28
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! (1,001 reviews)
"Hotel was clean and stag was helpful and friendly."

Reviewed on Sep 2, 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 ₩314,833 per night from Sep 28 to Sep 29
₩314,833
₩351,668 total
Sep 28 - Sep 29
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 1,007 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.
Two Brooks Lodge

Two Brooks Lodge

3 out of 5
1054 Sawmill Rd Bennington VT
Stay at this vacation home in Bennington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Robert Frost Stone House Museum and Harmon ...
4.8/10 (3 reviews)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in ..."

Reviewed on Apr 20, 2023

Two Brooks Lodge
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.6/10 Excellent! (83 reviews)
"Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained"

Reviewed on Jan 31, 2026

Long Trail House at Stratton Mountain Resort
See all 814 properties in 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