My Local MA

Where to Rest & Recharge in the Berkshires

Dream. Plan. Travel.

Winter is a time of renewal, a chance to hibernate and rest during the dark hours of short snowy days and long starlit nights. Unfortunately, most of our lives, defined by demanding jobs, pinging electronics, and endless to-do lists, make this time of year just as depleting as any other, sometimes more so after a festive holiday season. If you find yourself dreaming of a respite—sipping wine with a best seller by firelight, pampering yourself poolside after a massage, or thrilling your senses on a black diamond slope—the Berkshires is truly your dream destination. Whether you can travel safely now or are simply ready to immerse yourself in the joys of planning a future getaway, our many cozy inns, historic hotels, and luxurious resorts are ready to book your stay.

The Williams Inn. Ryan Bent Photography.

After a day of strolling the vast corridors of MASS MoCA, skiing at Berkshire East, or exploring the campus of Williams College and the many shops along Spring Street, check into the upscale Williams Inn to rest and recharge. The newly renovated hotel—a contemporary design of stone and beam that echoes the local architecture of a farmhouse—offers a full-service restaurant and bar aptly named The Barn. Elegant rooms and suites boast beds with high thread count sheets, soothing wall colors, ornamental wares made by local craftsmen, and details reflective of the Inn’s attention to guest comfort (i.e. supremely soft black washcloths for makeup removal). Find equally comfortable accommodations down the road at Holiday Inn Berkshires (indoor pool, whirlpool, and two saunas), and TOURISTS, a hip hotel with a chill glamping vibe that offers guests experiences such as stargazing with s’mores and headlamp hikes. 

Lemon Curd Dutch Baby at 33 Main.

If you make central Berkshires your basecamp, consider staying at 33 Main, conceived and curated by Annie Selke, a home furnishings entrepreneur and local to Lenox. Built in 1836, the Federal style inn indulges guests from the moment they arrive—enjoy freshly baked cookies, a cocktail hour with nibbles, and a plethora of bath goods from the award-winning Farmaesthetics line (all natural and certified organic). In the morning, dine on a gourmet breakfast. Because the inn is small, guests must be 21 or older. For a delightful B&B experience, check out the restored Victorian-style Rookwood Inn (with fire-placed parlor, veranda and gardens). Before booking a gorgeous room at the Inn at Kenmore Hall, you can take a virtual tour of this spectacular Georgian estate set on 20 acres near Tanglewood and Hancock Shaker Village. Craving a healing sanctuary? Treat yourself to a night or two at Canyon Ranch or Miraval Berkshires—both resorts offer an impressive selection of services focused on mind-body wellness. When you tire of relaxing in your stay of choice, take a scenic walk through downtown Lenox where you can admire local photography at Sohn Fine Art, shop for gifts at An American Craftsman, or spruce up your wardrobe at Casablanca and Shooz. Stop into Laurie Donovan Designs for handmade and antique jewelry.

Also centrally located in the city of Pittsfield is Hotel on North, a boutique hotel with charming eclectic décor and exposed-brick in a 19th century building. Take a short walk to visit Berkshire Museum, Barrington Stage Company, and numerous restaurants, coffee shops, and yoga studios. Enjoy a fine meal and craft cocktail at their on-site restaurant, and pick up stylish home goods, accessories, and souvenirs at Dory & Ginger, a shop attached to the hotel’s lobby. If you travel with your pup, Hotel on North is an excellent choice—many rooms are pet friendly.

Gedney Farm Barns in winter.

For southern stays check out Shaker Mill Inn in West Stockbridge (children and pets welcome), or Fairfield Inn & Suites – Berkshires (indoor pool and complimentary breakfast) in Great Barrington. If you’re looking for a more secluded experience, book a room at Gedney Farm in New Marlboro where you can recharge in one of 16 guestrooms and suites—many featuring granite fireplaces and whirlpool tubs—in a restored Normandy-style barn. It’s a perfect respite after tubing at Ski Butternut or snowshoeing at one of the many properties cared for by The Trustees or Berkshire Natural Resources Council.

Find many additional hotels, inns, bed and breakfasts, and resorts here. All lodging properties in the Berkshires are following strict COVID-19 protocols. Some, like TOURISTS, require multi-night stays, so be sure to make note of policies and guidelines when booking. Even if you plan to travel later in the year, book now to reserve the accommodation of your choice.

No matter when you arrive, during the romance of a snowy winter, the vibrancy of a bustling summer, or the blazing beauty of our showy fall, the Berkshires is eager to welcome you. All you have to do is dream, plan, and travel when the time is right.

By Elizabeth Nelson, Sr. Marketing Specialist for 1Berkshire