Old Bennington Travel Guide

Tourist Guide

Bennington Battle Monument featuring 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 showing landscape views
Old Bennington
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road, Bennington, VT
Stay at this 4-star golf B&B in Bennington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
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 2 Sept 2025

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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 3.418.134 ₫ per night from 12 Nov to 13 Nov
3.418.134 ₫
3.818.055 ₫ total
12 Nov - 13 Nov
includes taxes & fees
Stay at this 3-star hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,005 reviews)
"Good facility in a not great neighborhood. Very helpful and friendly staff."

Reviewed on 12 Oct 2025

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is 5.574.861 ₫ per night from 11 Nov to 12 Nov
5.574.861 ₫
6.227.119 ₫ total
11 Nov - 12 Nov
includes taxes & fees
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their ...
9.6/10 Exceptional! (520 reviews)
"Lovely clean room with a fabulous shower. Tea/coffee available 24 hours with a choice of milks which is great. Refillable glass bottle in the room to collect fresh water which meant no plastic bottles. Plenty of parking, cosy lobby and restaurant food excellent."

Reviewed on 10 Oct 2025

The Williams Inn
See all 973 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.
Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

3 out of 5
Bennington
Stay at this 3-star business-friendly cottage in Bennington. Enjoy free parking. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle ...
We recommend the place!
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."

Reviewed on 31 Jul 2024

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 3-star cottage in Bennington. Enjoy free parking, an in-room coffee maker and air conditioning. Popular attractions Bennington Center for the Arts ...
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
Stay at this 3-star ski aparthotel in Stratton. Enjoy free Wi-Fi, free parking and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (74 reviews)
"Nice, clean room in prime location"

Reviewed on 15 Mar 2025

Long Trail House at Stratton Mountain Resort
See all 771 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.

Popular places to visit

Bennington Battle Monument featuring landscape views

Bennington Battle Monument

4/5(3 reviews)

Learn about the local history of Old Bennington with a stop at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument
Old First Congregational Church

Old First Congregational Church

Find out about the history of Old Bennington when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.

Old First Congregational Church

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

You can spend an afternoon exploring the galleries in Hemmings Motor News Car Lover's Convenience Store & Vehicle Display during your travels in Bennington. While you're here, you can savour the cosy cafes.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

Prospect Mountain Cross-Country Ski Center

4/5(1 review)

Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.

Prospect Mountain Cross-Country Ski Center

Bennington Museum

You can spend an afternoon exploring the galleries in Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and cafes.

Bennington Museum

Bennington Potters Yard

You can do some window-shopping at Bennington Potters Yard during your trip to Bennington. Discover the cafes and its art scene while you're in the area.

Bennington Potters Yard

Cities near Old Bennington

Bennington Battle Monument featuring landscape views

Bennington