I Could Stay At This Berkshires B&B Forever

On a rainy Friday afternoon, we set out for a three-hour drive upstate. Our final destination: Harbour House Inn, a bed and breakfast in the Berkshires town of Cheshire. As soon as we pulled into the driveway, I knew we were in for something special. 

The History

Harbour House was built in 1793 and served as the main house on a chicken farm until the 1980s. Owners Brandi, Darrel, and Billie took over the property in February 2021, moving from Colorado to fulfill a lifelong dream of owning a B&B. The inn retains much of its vintage charm but the family has also added their touches: an Aspen Colorado bed that their son built, a vast collection of salt and pepper shakers from Brandi’s mother, pieces of furniture that belonged to great-grandparents. Everything in the inn has a story. 

The Bed & Breakfast

The inn has six rooms, each centered around a different theme. We stayed in Field Of Dreams, their biggest suite. I loved getting up in the morning, putting on the spa-style robe, and watching the cars drive past. It was a cozy and quiet oasis, a much-needed departure from the stress and chaos of the city. 

What sets Harbour House apart are the details. Walking through the front door, we were greeted by a twinkling Christmas tree, a roaring fireplace, and freshly baked chocolate chip cookies. The two sitting areas are filled with books and chairs for lounging, and it felt so festive with all the holiday touches.

Breakfast is served at 8:30 every morning, but this isn’t the continental breakfast of undercooked scrambled eggs and cold pancakes. On day one, we were served Eggs Benedict and a yogurt parfait with fresh fruit. Day two was a feast, with a slice of artichoke and potato quiche, sausage patties, and a blueberry muffin. Everything is made from scratch, taking into account dietary needs and allergies of the guests.

Brandi gave us ample recommendations since it was our first time in the Berkshires, and it was great to have a local perspective. During our stay, all the innkeepers went above and beyond to make sure that we were comfortable, warm, and taken care of. 

The Berkshires

Crowds flock to the Berkshires in the summer, but tourism slows in the colder months. However, the Massachusetts county has year-round attractions that are more than enough to fill a wintry weekend.

Harbour House is next to Mount Greylock, 20 minutes from North Adams, and 50 minutes from Great Barrington, making it a great jumping-off point. We spent an afternoon exploring the Mass MoCA, one of the largest contemporary art museums in the US. Downtown streets are filled with local stores, bookstores, bars, and coffee shops, perfect for a stroll. The inn is also minutes away from a range of hiking trails, like the Ashuwillticook Rail Trail and the Appalachian Trail—just make sure you’re wearing something warm

If we had more time, I would’ve loved to visit the Clark Institute in Williamstown or the Norman Rockwell Museum in Stockbridge.

If you don’t feel like venturing out, you can always hang out in your bed and breakfast and call it a vacation well spent. 

Why You Should Go

For a Berkshires getaway that’s perfect any time of year, head to Harbour House Inn Bed and Breakfast. You’ll easily fall in love with the home and hospitality and wish you booked your stay for longer.

Annika Olives

Staff Writer

Annika is a Manila-born, California-raised, and NYC-transplanted Filipino-Spanish-American storyteller. Her writing career has spanned from content design to journalism to social media, so she can craft seamless product copy, compelling articles, and killer captions with ease. She’s a techie by day but a creative always, and she loves all things wellness, lifestyle, food, travel, fashion, arts, and culture. Because she’s a Virgo rising and eldest daughter who doesn’t understand the concept of rest, she’s obsessed with perfecting the lazy girl routine and perhaps—one day—achieving that all-elusive leisure. Her simple joys include skincare that doesn’t break you out, chai lattes, baking, a good thrift find, and building trip itineraries on Notion.