Old Bennington, VT

Travel Guide

A statue with outstretched arms and a tall obelisk in the background.
A tall stone monument with a central entrance, surrounded by a well-maintained lawn and trees.
A white historic building with arched windows and a stone fence with headstones.
A lush green landscape with a prominent hill in the background, surrounded by dense forests and scattered houses.
A tall stone obelisk with a weather vane on top, set against a cloudy sky.
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 ...
9.4/10 Exceptional! (291 reviews)
"Very nice, quiet place. Relaxing and cute."

Reviewed on 7 September 2026

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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 AED 438 per night from Nov 1 to Nov 2
AED 438
AED 489 total
1 Nov - 2 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,001 reviews)
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."

Reviewed on 30 September 2026

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
The price is AED 645 per night from Nov 1 to Nov 2
AED 645
AED 720 total
1 Nov - 2 Nov
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! (683 reviews)
"Great"

Reviewed on 29 September 2026

The Williams Inn
See all 1,014 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.
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington VT
Book a stay at this family-friendly vacation home in Wilmington. Enjoy free WiFi, a sauna, and a garden. Our guests praise the helpful staff in our reviews. ...
10/10 Exceptional! (243 reviews)
"This house and property are absolutely beautiful and we can’t say enough good things about it! We had great weather and a fire every night. The game room was a huge hit for kids of all ages!Driveway is steep."

Reviewed on 7 September 2026

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham VT
Stay at this vacation home in Whitingham. Enjoy a garden, laundry facilities, and patios. Popular attractions Harriman Reservoir and Readsboro Community Library ...
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Pownal VT
Book a stay at this family-friendly apartment in Pownal. Enjoy free WiFi, private pools, and a garden. Popular attractions Solomon Wright Library and Solomon ...
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
See all 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.

Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the coffeehouses and its art scene while you're in the area.
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