“Chesterwood, Lenox, Berkshire County, Massachusetts” by MOTT is licensed under CC BY-ND 2.0. This is a fantastic choice for those visiting on a budget. Head down to Onota Lake where you can hire boats, fishing poles and kayaks for a fun day out among the stunning scenery. With wide leafy streets, a peaceful town centre, and spacious accommodation, Adams is the perfect destination for a family staycation! Want to be featured in our list? I think of all these towns, the "grande dame" is either Lenox or Stockbridge. Despite this, it’s also one of the most affordable destinations. The area is known for its hikes, festivals, and farm to table restaurants. Pssssst! Great Barrington is the Southern Berkshires’ “big” city, but it’s only big in comparison to the many villages that surround it. Whether you’re on a budget, want to stay close to the action, or are trying to plan a family-friendly vacay, we’ve got you covered. Our favourite travel backpack is the Aer Travel Pack 2. Guests will have quick access to the Mt Greylock pistes, with regular skiing and snowshoeing available. Lenox Athenaeum and Shakespeare & Company are also two fantastic theatres – the latter of which is a particularly excellent choice if you have kids. A long-time Berkshire resident, he’s peformed at Tanglewood 25 times since 1974. Found three hours from Manhattan and two hours from Boston, Great Barrington is the sort of humble community where everyone knows your name yet where you can at present discover sushi at 3 AM. restaurants in the town centre – we love the Underground in particular, who also provide live entertainment. Step back in time with this traditional hideaway in the heart of Adams. They’re easy to use, professional and relatively affordable. The affordable rates make this a great choice for couples and small families heading to the region on a budget. It’s all about helping out our tribe of awesome backpacker readers [that’s you!]. All rights reserved. This creative hub is a must-visit for anyone interested in discovering cultural highlights. Just south of Pittsfield, Lenox is a great option for your first-time in The Berkshires. Did we miss anything? Beyond family-friendly attractions, Adams is also the best area in the Berkshires for adventurous travellers. The towns are pretty easy to get to, and public transport connections are actually pretty good. In the 19th century, the Vanderbilts, Carnegies, and Westinghouses summered in Lenox, building grand villas known as Berkshire cottages and turning the hamlet into the Gilded Age equivalent of the Hamptons. That being said, Lenox is a good alternative if you want to get creative, and Pittsfield is a great way to experience the Berkshires without breaking the bank. Just be warned, this post is full of awesome recommendations including the best place to stay, what to do, and where to eat while visiting the Berkshires, so don’t blame me if you find yourself booking a getaway by the end of this! Situated on 30 acres, this scenic Berkshires bed and breakfast boasts a heated, seasonal outdoor pool and on-site tennis courts. I have been using World Nomads for some time now and made a few claims over the years. There are also more shopping destinations here – ranging from national chains to local boutiques. After exploring the best towns in the Berkshires, we invite you to return to Lenox for some well-deserved relaxation in our elegant bed & breakfast. Of course, when it comes to skiing, you can’t go wrong with this peaceful home within walking distance of Mt Greylock! Airbnb's Most Unique Properties Worldwide. The Berkshires are home to some cute destinations perfect for a laid-back USA travel experience. Save. The Berkshires Vacations Save more by combining flights, hotels and cars. “I’ve seen sunny days that I thought would never end.” Yes, Berkshire County is having its day in the sun. This creative hub is a must-visit for anyone interested in discovering cultural highlights. Visiting in the winter? Pittsfield is the largest town in The Berkshires, so it might seem surprising that it’s our top budget pick. We'll assume you're ok with this, but you can opt-out if you wish. We plan to start in Savannah and drive to the Berkshires from Pennsylvania. For the sake of transparency, some of the links in our content are affiliate links. Which is where we come in! With small-town charm and big-city culture, winter sports for novices and adrenaline addicts, and learning experiences that feel more like recess than school, you’re in for a colorful adventure. The towns of the Berkshires are quite spread out so there really isn't a central location. Pittsfield is home to some interesting cultural attractions, including a few museums. Pittsfield is the largest town in The Berkshires, and a major gateway into the region. Close, Where to Stay in The Berkshires (2021 • COOLEST Areas!). Featuring country roads, farmers’ markets, bookstores, galleries, and cultural mainstays such as Tanglewood, Mass MoCA, and the Williamstown Theater Festival, here are the top 4 vacation towns in the Berkshires. Hotel on North comes with outstanding guest reviews thanks to their above-and-beyond service and unmatchable comfort. You’ll have to splurge, but with five stars and an award-winning wine menu, you’ll have the meal of your life at Blantyre. We work hard to put out the best backpacker resources on the web, for free! There are loads of towns and villages in the area, with each offering something a little different. The Norman Rockwell Museum, founded in 1969, is set on 36 scenic acres and features the largest collection of Rockwell art in the world. Stockbridge boasts one of the oldest continuously operating historic inns, too. Plan the Ultimate Berkshires Getaway With the Gateways Inn. Read the reviews and book. The Berkshires is a safe travel destination, but keep an eye on the weather, especially if you’re traveling during winter. Discover the best places to explore near The Berkshires with curated recommendations from our team of travel experts. If you and your sweetheart are thinking about a weekend getaway to the Berkshires this winter, we want to help make your stay at the Gateways Inn extra special. And quaint towns no matter the season beauty perfect for unwinding and letting your troubles melt away the foothills the. Town’S portion of the region yourself be whisked away into the fairytale with. Prior to arrival, making it a firm favourite with creatives carte is! 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