Name: Hotel Downstreet, an Ascend Collection Hotel
Price range: ￥17,375
Rating: 8.6

The Four Chimneys Inn

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 ...

9.6/10 Exceptional! (223 reviews)

This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again.

Reviewed on Jan 12, 2026

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The Williams Inn

101 Spring Street Williamstown MA

￥29,780

￥33,264 total

Mar 11 - Mar 12

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! (573 reviews)

A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff.

Reviewed on Feb 7, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

￥17,375

￥19,408 total

Mar 17 - Mar 18

includes taxes & fees

Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...

8.6/10 Excellent! (1,001 reviews)

Room was cozy and clean. Staff was very responsive and courteous. The entire place was great from location to feel.

Reviewed on Feb 1, 2026

See all 1,008 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.

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover VT

Book a stay at this ski condo in West Dover. Enjoy a fitness center, tennis courts, and ski-in/ski-out access. Popular attractions Mount Snow and Seasons Ski ...

8.2/10 Very Good! (25 reviews)

Great place with great amenities!

Reviewed on Nov 18, 2025

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 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! (208 reviews)

Tony was great at communicating.

Reviewed on Feb 8, 2026

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

Wilmington VT

Stay at this cabin in Wilmington. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Mount Snow and The Hermitage Golf Club are located ...

6.4/10 (6 reviews)

The house was clean and well set up We had everything we needed and moreIt was a wonderful place to stay!

Reviewed on Oct 28, 2025

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.

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Popular places to visit

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.

Prospect Mountain Nordic Ski Center

Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and coffeehouses.

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.

Woodford State Park

You can take time to visit Woodford State Park during your travels to Woodford.

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.

Southern Vermont College

Explore the campus of Southern Vermont College, during your travels in Bennington. While you're here, you can savor the charming coffeehouses.

Old Bennington, VT

Travel Guide

Visit Old Bennington