Find hotels in Bennington, NY from $62

The best area to stay in Bennington is the historic downtown district, particularly around Main Street and North Street.This area is the heart of Bennington, offering a blend of historic architecture, local shops, and dining establishments. It's easily walkable, with many points of interest clustered together, including the Bennington Museum and the Bennington Battle Monument a short drive away.For couples looking for a relaxed and culturally enriching experience, this downtown area is ideal. You'll find charming local eateries, art galleries, and easy access to historic sites, making it convenient to explore at a leisurely pace.Travelers seeking a comfortable and well-connected base will also appreciate staying downtown.

The best times to visit Bennington are during the summer months, from June to August, and the fall season, particularly October, to experience the area's natural beauty.Summer in Bennington offers pleasant weather, with warm days superb for exploring the outdoors. You can enjoy hiking the trails around Mount Anthony, visiting the Bennington Battle Monument, or taking scenic drives through the countryside. This season is ideal for families looking for outdoor activities and comfortable temperatures.For those interested in fall foliage, October is an excellent time to visit. The surrounding Green Mountains transform into a spectacle of vibrant colors, making it a popular time for scenic drives and photography.

With Expedia, you earn OneKeyCash™* on eligible Bennington hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.