Old Bennington

Travel Guide

Bennington Battle Monument which includes landscape views
Bennington Battle Monument which includes a monument and heritage elements
Bennington Battle Monument which includes a small town or village and landscape views
Bennington Battle Monument featuring 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 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

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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 P7,559 per night from Nov 12 to Nov 13
P7,559
P8,443 total
Nov 12 - Nov 13
includes taxes & fees
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,003 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"

Reviewed on Oct 9, 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 P12,330 per night from Nov 2 to Nov 3
P12,330
P13,773 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 4-star 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! (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 Oct 10, 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 Jul 31, 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
Stay at this 3-star cottage in Bennington. Enjoy free parking, an in-room coffeemaker, 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 WiFi, 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 Mar 15, 2025

Long Trail House at Stratton Mountain Resort
See all 770 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 which includes landscape views

Bennington Battle Monument

Learn about the local history of Old Bennington when you spend time 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 with a stop 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 browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.

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

Prospect Mountain Cross-Country Ski Center

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 studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.

Bennington Museum

Bennington Potters Yard

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

Bennington Potters Yard

Things to do

Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway

Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway

P988
per traveler
100% of travellers recommend
Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway
Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

P988
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Old Bennington