10 Best Berkshires Hotels and Homes To Book For A Weekend Away

The Berkshires region, located in western Massachusetts, less than a three hours’ drive from New York City, boasts hiking trails just as incredible as its antiquing scene, making it the ideal weekend departure for any kind of traveler. Think fireplaces, darling B&Bs, and of course, accessible Wi-Fi. It’s not that kind of unplugged. If you’re in the mood for an outdoors-heavy weekend, look to stay close to Great Barrington, where ski culture rules all year round. Fans of the History channel will love a stay near Stockbridge, where a picturesque small town highlights the history of the mountainous region. And those looking to indulge in all things culture need look no further than Tanglewood and Jacob’s Pillow.

Take a more personality-based approach to booking your time in the Berkshires by considering the kind of home away from home you’re after. Cozy cottage with some Victorian flair? Photo-ready luxury hotel with just the right amount of New Yorkers on vacation? Options abound in this often-overlooked stretch of glorious mountains and hidden New England gems. Read on for the Berkshires hotels and rentals we highly recommend for your next trip.

Berkshires Hotels

TOURISTS – North Adams, Massachusetts

There’s a thin line between overly curated and impeccably arranged. Tourists, a hotel with a sizable social following, sits staunchly on the side of great arrangements. A restaurant in the hotel worth the trip, unique guest rooms in muted palettes, and a compelling list of on-site activities, make this the perfect spot for the traveler in the mood to get social. Plus, it’s dog-friendly for those traveling with canine companions.

Wheatleigh – Lenox, Massachusetts

Wheatleigh, tucked in a forest of evergreens, is the most luxurious take on a getaway in the Berkshires. Inspired by the original owner’s ancestral home in Oxford, England, the elevated sense of isolation is woven into every inch of this estate. It only makes sense that the restaurant on the property has eight tables with a tasting menu.

The Porches Inn at Mass MoCA – North Adams, Massachusetts

Those looking to experience small-town living in the Berkshires should stay at The Porches Inn, located in North Adams. The hotel itself features unique designs in every room that makes up the row of converted 19th-century mill workers’ cottages. Sojourning at this hotel, neighboring the Massachusetts Museum of Contemporary Art (MASS MoCA), makes immersing oneself in the local arts scene as simple as stepping out of the front door.

Hotel on North – Pittsfield, Massachusetts

If you skew quirky or eclectic, a stay at Hotel on North would make for the ideal weekend. Inside, a birdcage elevator stands as a two-person cocktail bar and “lightning-fast Wi-Fi beams through exposed brick from the 1880s,” according to the website. This 45-room boutique hotel, which is centrally located among all the greatest hits that the Berkshires region has to offer, makes for an absolutely cheeky stay.

Blantyre – Lenox, Massachusetts

This Tudor-style mansion, built in 1902, stands stoically in Lenox. Expect to live as in the Gilded Age, even beyond the architecture: lobster picnics on sprawling lawns, dimmed lights by blazing fireplaces, vintage champagne that simply appears. Rooms are simple in the most elegant way. If you were planning a daylong hike with a cold beer as your only evening endeavor, this hotel might not be your perfect fit.

Private Homes

The Filomena – Stockbridge, Massachusetts 

Channel your inner Wes Anderson with a stay at this impossibly inspiring home filled with quirky details and thoughtful color choices. The adjoining garden takes the charm factor through the roof. A renovated 19th-century rectory, we’ve already dubbed it “the coolest Airbnb in Massachusetts” for a reason. The Norman Rockwell Museum also resides in Stockbridge for a fun day activity.

Fun Farmhouse – Great Barrington, Massachusetts

This house, also available on VRBO, is exactly what your group chat had in mind when someone proposed a weekend trip three months ago. An outdoor pool makes for the perfect sunny solace in warmer months. Its proximity to some of the state’s skiing makes a strong argument for visiting during the winter and it sleeps eight, so no one has to be left out of the festivities.

Midcentury Modern Retreat – Lanesborough, Massachusetts

Ever dreamed of calling a spacious midcentury-modern estate home? I mean, who hasn’t? Try the look on for size with this lovely home complete with an office. Work from anywhere just might mean Lanesborough.

1817 Farmhouse – Lee, Massachusetts

Cozy in for a charming stay at this one-bedroom cottage in Lee, Massachusetts. Located at the foot of October Mountain State Forest, near Lee, Lenox, and Pittsfield, this 1817 home has much of the original detailing, such as wood beams and floors. If you’re comfortable climbing stairs, make this your home away from home for a relaxed weekend.

Cleveland House – Dalton, Massachusetts

A tavern/stagecoach stop in the 1800s, this renovated gem is centrally located within the Berkshires. Cozy nooks dot the mostly-black-and-white space. The outdoor deck, which is fully furnished, is great for entertaining outdoors. With six bedrooms, you better start sending out invites.