Find Hotels with Bars in Sheffield, MA

Sheffield features 31 hotels and other lodging options to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you’re here, you can check out Housatonic River and Magnolia Bluffs Casino.

Here are some favorite hotels with bars in and around Sheffield: Wilder House Berkshires: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Berkshires Untold: Enjoy the poolside bar, 2 outdoor pools, and WiFi. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Enjoy the bar, free breakfast, and free WiFi. The Yankee, Trademark Collection by Wyndham: Hotel with 3 restaurants. Enjoy the bar, free WiFi, and breakfast. The Black Swan Lee - Lenox, Ascend Hotel Collection: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.

If you have time to explore, consider visiting Ski Butternut, Lake Buel, and Mahaiwe Performing Arts Center, and then find a cozy spot for a nightcap. Other places to see include Housatonic River and Magnolia Bluffs Casino.

Visiting local bars in Sheffield is more fun when you know what the weather holds. These rainfall averages and temperatures can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Here are some of your transportation choices in and around Sheffield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.