Travel Guide: The Berkshires These recommendations for where to stay, what to do, and what to eat on your next Extra Holidays getaway are vetted by our team. I traveled to The Berkshires to bring you this in-depth guide for planning an Extra fall getaway. Where to stay: Club Wyndham Bentley Brook Located in Hancock, Massachusetts, Club Wyndham Bentley Brook is the perfect home base for your trip to The Berkshires. Nestled at the base of Jiminy Peak Ski Mountain, this resort is a popular destination in the winter. However, there's plenty to do at the resort, and nearby, year-round! It's only five minutes from the New York border, and 20 minutes from the Vermont border. If you're looking for a quiet and cozy escape this Fall – look no further. This resort is centrally located to explore nearby Berkshire County towns and attractions, but is also a great spot for a quiet getaway. Step out onto your balcony for amazing nature views, bake some cookies in your kitchen, or head to the movie theater with your family. This is the perfect resort to unwind after exploring The Berkshires. I stayed in a spacious two-bedroom suite that slept up to eight guests. It had a full kitchen, dining area, living room, two bathrooms, a pull-out sofa, whirlpool tub in the master, balcony, and washer and dryer. This suite is perfect for large families or friend groups traveling together. Some of my favorite moments from this trip were cooking breakfast in the kitchen and then enjoying it and a cup of coffee on the private balcony. Just look at the view! With amenities like a movie theater, hot tub, indoor and outdoor pool, sauna, tennis courts, and picnic area – there is truly something for everyone. Club Wyndham Bentley Brook also offers daily activities like painting your own wine glasses and Tequila Tuesday margaritas. Travel tip: fly into Albany International Airport. Where to eat: While The Berkshires isn't typically known as a foodie destination, I found some good eats that are worth adding to your list: Blueberry Hill Market Café: Probably my favorite breakfast/lunch spot the whole trip. Amazing food, amazing coffee, and amazing views. Mazzeo's Ristorante: This is a great spot for a nicer night out! This restaurant has been a Best of the Berkshires Reader's Poll Winner 8 years in a row. Gardner's Ice Cream and Coffee Shoppe: Ice cream and mini golf? Yes please. Gino's Pizza & Grill: Having a night in at the resort? Order delivery from Gino's Pizza & Grill. They'll deliver right to your room. The Village Chocolate Shoppe: If you find yourself exploring nearby towns, visit The Village Chocolate Shoppe in Bennington, Vermont. The chocolate is made fresh in-shop daily and it's SO good. What to do: Hilltop Apple Orchards: Home of Furnace Brook Winery: Is it even Fall if you don't go apple picking? Visit Hilltop Apple Orchards to pick apples and do a wine tasting. Don't leave without trying the apple cider donuts – I think they're the best donuts I've ever had. Mount Greylock: Mount Greylock is the highest point in Massachusetts – you can drive up or hike to the top. Balderdash Cellars: Wine tastings, food trucks, live music, and amazing views. A visit to Balderdash Cellars is a must. Ioka Valley Farm: This farm is less than 10 minutes from Club Wyndham Bentley Brook and is home to a pumpkin patch, corn maze, animal farm, and more. This is a great spot for families. The Apple Barn & Country Bake Shop: Take a scenic drive towards Vermont and stop by The Apple Barn for homemade pastries and fudge, apple cider, produce, and gifts. Downtown Bennington: For antique stores, bookstores, and local shops visit Downtown Bennington. Thanks for exploring our Travel Takeover in The Berkshires! To see a full room tour and video content from our stay, follow us on Instagram at @extraholidays and on TikTok at @extraholidays.
