Best Hotels in Berkshire County for 2025

Hotel Downstreet, Ascend Hotel Collection's great location gets high marks from our customers. During your stay, you're just a quick walk from Western Gateway Heritage State Park. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.

Our customers tell us that they can't get enough of the helpful staff at Vacation Village in the Berkshires. During your stay, you'll be within walking distance of Jiminy Peak Mountain Resort. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool. This comfortable condo has 360 condos over 2 floors. A kitchen and a washer/dryer are available in each condo.

Our customers tell us that they can't get enough of the helpful staff at Life House Berkshires. During your stay, you'll be within walking distance of Kennedy Park. Free WiFi in public areas, free self-parking and a restaurant are available.

Our customers tell us that they can't get enough of the helpful staff at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires. During your stay, you're just a quick walk from Beartown State Forest. Enjoy features like 2 indoor pools, 2 restaurants and 2 bars.

Our customers tell us that they can't get enough of the helpful staff at The Williams Inn. During your stay, you're just a quick walk from Williams College. Features include free WiFi in public areas and free self-parking, plus a restaurant.

Our customers tell us that they can't get enough of the helpful staff at The Red Lion Inn. During your stay, you're just a quick walk from Housatonic River. Enjoy features like free WiFi in public areas, plus 3 restaurants and an outdoor pool.

Our customers tell us that they can't get enough of the free breakfast at The Yankee, Trademark Collection by Wyndham. During your stay, you're just a quick walk from Guido's Marketplace. Features include free WiFi in public areas and free self-parking, plus an indoor pool.

Our customers tell us that they can't get enough of the helpful staff at Holiday Inn & Suites Pittsfield-Berkshires by IHG. During your stay, you're just a quick walk from Berkshire Museum. Features include free WiFi in public areas and free self-parking, plus an indoor pool.

Our customers tell us that they can't get enough of the helpful staff at Berkshire Mountain Lodge. During your stay, you're just a quick walk from Guido's Marketplace. Free WiFi in public areas, free self-parking and an indoor pool are available.

Our customers tell us that they can't get enough of the helpful staff at Hotel On North. During your stay, you're just a quick walk from Barrington Stage Company. You'll find features such as free WiFi in public areas and free self-parking, plus a gym. This property offers pet-friendly amenities, such as food and water bowls.

Our customers tell us that they can't get enough of the helpful staff at The Little Lion. During your stay, you'll be within walking distance of Housatonic River. Features include free WiFi in public areas and free self-parking.

The free breakfast at Quality Inn gets good marks from our customers. During your stay, you're just a quick walk from Mahaiwe Performing Arts Center. Free WiFi in public areas, free self-parking and a free manager's reception are available.

Our customers tell us that they can't get enough of the helpful staff at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires. During your stay, you're just a quick walk from Housatonic River. Enjoy features like free breakfast, free WiFi in public areas and free self-parking.

The free breakfast at The Constance, The Whitlock, & The Dewey By The Lenox Collection gets high marks from our customers. During your stay, you're just a quick walk from Lenox Library. Free WiFi in public areas, free self-parking and a gym are available.

Our customers tell us that they enjoy the free breakfast at Fairfield Inn & Suites by Marriott Williamstown. During your stay, you'll be within walking distance of Williams College. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.