Great Mountainside Getaway for Couples in The Berkshires, Massachusetts

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couple by the fire

 

Have a cozy winter vacation



In the cooler months, the Berkshires are the perfect place to visit for a cozy retreat with your partner. Nestled in the Appalachian Mountains, the region transforms into your classic winter wonderland every year. From December through February, you can expect frigid temperatures and mountains coated in white. If you and your significant other enjoy skiing or snowboarding, you’ll be in paradise on a trip to the Berkshires. Ski resorts like Jiminy Peak, Butternut, Catamount, and Bousquet are all fantastic, easily accessible mountains in the area to shred during your stay.

There are also plenty of opportunities for cross-country skiing and snowshoeing scattered across the region. If you choose to do either, we recommend you head out to Hill Top Orchards. There, you’ll find stunning countryside and an onsite winery, where you can warm up with a glass of vino or a cup of hot cocoa.

One of the best things about the cold is getting snug and comfortable indoors with your loved one. For a particularly homey stay, book a reservation at the Race Brooke Lodge. At this bed and breakfast, you’ll find a candlelit tavern, live music, and beautiful wood cabin decor.

Enjoy hiking and swimming in the Berkshires

Lake in the Berkshires



While there is plenty to do in the winter, the doors open up for even more charming date ideas with your partner when the weather heats up. From October through May, you likely won’t be interested in getting in your bathing suit. However, in the warmer months, the Berkshires have a variety of scenic lakes for you and your loved ones to cool off in and explore. For crystal clear waters and a lively atmosphere, we would suggest you head to Lake Onata in Pittsfield, MA. If you’re looking for something a little more serene and less crowded, check out the glacial Lake Buel.

While amidst the Berkshires’ rolling hills, you’d be remiss if you didn’t hike through one of its many tranquil trails. For a beautiful view overlooking Mount Greylock, take the 6-mile round-trip hike to Spruce Hill. If you plan your visit in the autumn, you’ll be surrounded by unparalleled vibrant leaves on any hike you choose. But, for a particularly breathtaking view of the fall foliage, make sure to take on the Hoosac Range Trail.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.