Old Bennington

Travel Guide

Bennington Battle Monument which includes landscape views
Bennington Battle Monument showing heritage elements and a monument
Bennington Battle Monument featuring a small town or village and landscape views
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 WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
"The owners are there everyday. The staff is friendly and very custimer focused. The standards are high and the inn has a great history and is lovely. It felt more like being a house guest than a customer. The restaurant was an outstanding choice for dinner and accommodation for vegetarians and allergies ..."

Reviewed on 27 Mar, 2025

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The Four Chimneys Inn
Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
The price is S$206 per night from 13 Jul to 14 Jul
S$206
13 Jul - 14 Jul
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! (999 reviews)
"Noises heard through walls from adjoining rooms. Staff friendly and helpful with suggestions. Free local coffee and fresh apples in main lobby."

Reviewed on 9 Jun, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is S$308 per night from 9 Jul to 10 Jul
S$308
9 Jul - 10 Jul
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! (456 reviews)
"Beautiful property. Very clean. Short distance to campus."

Reviewed on 10 Jun, 2025

The Williams Inn
See all 951 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!
Two Brooks Lodge
Two Brooks Lodge
3 out of 5
1054 Sawmill Rd, Bennington, VT
Stay at this 3-star vacation home in Bennington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Robert Frost Stone House Museum and ...
"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 20 Apr, 2023

Two Brooks Lodge
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!
See all 739 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

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

Things to do

Vermont RT 100: Self-Guided Driving Audio Tour

Vermont RT 100: Self-Guided Driving Audio Tour

S$19
per traveller
Vermont RT 100: Self-Guided Driving Audio Tour
See all activities in Old Bennington
Bennington Battle Monument which includes landscape views

Bennington