What better way to take in seven acres of wooded land in the Southern Berkshires than through floor-to-ceiling glass walls in an octagon-shaped Airbnb? There’s not a bad seat in the house, especially around the living room’s Scandinavian-style wood-burning fireplace. Why you should stay: Spectacular views of the Berkshires from a one-of-a-kind home. Related Read: 7 Spectacular Weekend Road Trips from Boston, Massachusetts 1. Ready to plan? Here are 10 of the best, coolest, and most unique Massachusetts Airbnbs – there’s something for every type of traveler, budget, and adventurer on this list. But if Massachusetts is too far from you for a weekend getaway, you won’t regret spending a whole week here – between outdoor recreation, American history, and waterfront adventures, there’s plenty in the state to fill your days.

Massachusetts is easy for anyone on the eastern seaboard to reach, especially those in New York, who can take a leisurely train ride to Boston and spread out from there.

To those who’ve explored The Bay State’s striking coastlines, rolling hills, and bustling cities, it’ll come as no surprise that Rough Guides included Massachusetts on their list of best places to travel in 2020. See our editorial policy to learn more.ĭespite being one of the smallest states in the country, Massachusetts is home to fabulous getaways, from mountain retreats in the Berkshires to breezy trips along the coast. We may earn a commission when you book or purchase through our links. We research, evaluate and select travel destinations based on a number of factors, including our writers’ experience, user reviews and more.

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