Old Bennington, VT

Travel Guide

Bennington Battle Monument showing landscape views
Bennington Battle Monument which includes a monument and heritage elements
Bennington Battle Monument which includes landscape views and a small town or village
Bennington Battle Monument which includes landscape views
Old Bennington
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
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 ...
9.6/10 Exceptional! (222 reviews)
This is a beautiful, historic property and pretty consistent with the photos on the website. The room I had was just as pretty with some antique furnishings, but of course in person you notice that it is an old building. The room was a great size, and I loved the hardwood floors. The bathroom was ...

Reviewed on Sep 2, 2025

The Four Chimneys Inn
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is ₩289,283 per night from Dec 1 to Dec 2
₩289,283
₩323,129 total
Dec 1 - Dec 2
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 ...
9.6/10 Exceptional! (544 reviews)
Bb

Reviewed on Nov 17, 2025

The Williams 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 ₩157,191 per night from Dec 20 to Dec 21
₩157,191
₩175,582 total
Dec 20 - Dec 21
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,007 reviews)
Wonderful Experience

Reviewed on Nov 23, 2025

Hotel Downstreet, an Ascend Collection Hotel
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.
Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

3 out of 5
Bennington VT
Book a stay at this business-friendly cottage in Bennington. Enjoy free parking. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle ...
8/10 Very Good! (2 reviews)
Two things can improved: 1). The bathroom needs to be renovated. It has a dirty look. 2). The security alarm was beeping irritatingly all the first night. This prevented us from getting anywhere near a good night sleep. I did not find the owner very responsive. He said someone would be there by 4 ...

Reviewed on Oct 21, 2025

Bennington Gem w/ Smart TV Near Historic District!
Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!

3 out of 5
Bennington VT
Stay at this cottage in Bennington. Enjoy free parking, an in-room coffeemaker, and air conditioning. Popular attractions Bennington Center for the Arts and ...
Breathtaking Mtn Views: Stylish Rustic Retreat!
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 ...
8.4/10 Very Good! (77 reviews)
Nice lodge. Room needs updating

Reviewed on Oct 19, 2025

Long Trail House at Stratton Mountain Resort
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.

Popular places to visit