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! (218 reviews)
"Nice and cozy"

Reviewed on Jul 13, 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 P9,183 per night from Aug 20 to Aug 21
P9,183
P10,258 total
Aug 20 - Aug 21
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)
"Great place"

Reviewed on Jul 16, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is P15,382 per night from Aug 17 to Aug 18
P15,382
P17,182 total
Aug 17 - Aug 18
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! (471 reviews)
"My daughter and I stayed here overnight for a Williams visit. Very convenient, upscale hotel - basically in the middle of campus. My daughter did not like the modern farmhouse vibe, but I thought it worked well with the location."

Reviewed on Jul 18, 2025

The Williams Inn
See all 949 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!
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 Norman Rockwell Exhibition and Robert ...
"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
Home Near Hiking Biking w Hottub 6 Bedrooms

Home Near Hiking Biking w Hottub 6 Bedrooms

2 out of 5
Bennington
Stay at this vacation home in Bennington. Popular attractions Harmon Hill and Bennington Potters Yard are located nearby.
Home Near Hiking Biking w Hottub 6 Bedrooms
See all 744 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

P958
per traveler
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

P958
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Old Bennington