Best Hotels in Berkshire County for 2026

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 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 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 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.

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.

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.

During your stay at Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, you're just a quick walk from Guido's Marketplace. Features include free breakfast, free WiFi in public areas and free self-parking.

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.

During your stay at FairBridge Inn Express, you'll be within walking distance of Crane Museum of Papermaking. Free WiFi in public areas, free self-parking and a business centre are available.

Our customers tell us that they can't get enough of the helpful staff at Best Western Plus Berkshire Hills Inn & Suites. During your stay, you'll be close to Hancock Shaker Village. Enjoy features like free breakfast, free WiFi in public areas and free self-parking. This property offers pet-friendly amenities, such as an off-lead area.

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.

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 breakfast, free WiFi in public areas and free self-parking.

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 The Whitlock. During your stay, you're just a quick walk from The Bookstore. Enjoy features like free WiFi in public areas and free self-parking, plus a business centre.

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.