Best Hotels in Berkshire County for 2026

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 Berkshires Untold. 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.

Hotel Downstreet, an Ascend Collection Hotel's great location gets high marks from our customers. During your stay, you're just a quick walk from MCLA Gallery 51. 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 fireplace and a patio are available in each condo.

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. Free WiFi in public areas, free self-parking and 3 restaurants are available. This property offers pet-friendly amenities, such as food and water bowls.

The free breakfast at Hampton Inn & Suites Berkshires-Lenox gets high marks from our customers. During your stay, you'll be within walking distance of Guido's Marketplace. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool. Some of the pet-friendly amenities that this property offers include food and water bowls, an off-lead area and litter trays.

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 by IHG. During your stay, you're just a quick walk from Housatonic River. Enjoy features like 2 indoor pools, a poolside bar and a coffee shop/cafe.

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 Denison Park. 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 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 bar. This property offers pet-friendly amenities, such as food and water bowls.

The free breakfast at Quality Inn Great Barrington 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 free breakfast at The Yankee Inn. During your stay, you'll be within walking distance of 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 Courtyard by Marriott Lenox Berkshires. During your stay, you're just a quick walk from Kennedy Park. Enjoy features like free WiFi in public areas and free self-parking, plus an indoor pool.

The free breakfast at The Porches Inn at Mass MoCA gets high marks from our customers. During your stay, you're just a quick walk from Bracewell Park. Free WiFi in public areas, free self-parking and an outdoor pool are available. 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 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 valet parking, plus an indoor pool.

Our customers tell us that they can't get enough of the helpful staff at The Cornell Inn, Lenox & The Berkshires. During your stay, you'll be within walking distance of The Bookstore. Free breakfast, free WiFi in public areas and free self-parking are available.