The Best Hotels to Book in the Berkshires, Massachusetts

Vacation like a character in a late 19th-century novel at this luxury country house. History buffs who appreciate refined furnishings that ooze character will feel right at home in this 1902 manor. Period art and treasured heirlooms fill the baronial rooms and suites. Vintage wine fans will enjoy the opulent Dom Perignon salon. And if you’re eager to explore the history of the area, you’ll love cruising scenic driving routes via the exclusive BMW Experience, offering in-depth information on museums along the way.

Get away from it all, then go even further at the Old Inn on the Green. If you’re seeking total relaxation, this former stagecoach relay features restored guest rooms with cozy fireplaces and comfortable four-poster beds, where you can curl up with a long novel. Venture downstairs for a candlelit tasting menu of roasted red beet tarte tatin or pan-roasted breast of squab (pigeon). Watch the last light of day burn away in the evening on the quiet porch and breathe in the tranquility of the Berkshires.

Offering a full itinerary of activities, the Red Lion Inn is ready to curate the perfect trip for your family. Go cross-country skiing and tubing in winter, then come back for whitewater rafting and zipline canopy tours in the summer. Whatever the season, the staff will send you on an adventure to tempt you away from the luxurious bedding and feather duvets of your suite. Wait out a rainy afternoon in the quiet library researching other attractions in the area, or join other guests in the Lion’s Den for live entertainment.

Feeling outdoorsy? Then enjoy a harmonious stay at Race Brook Lodge. Lace up your boots, because the moment you set foot out of your rustic suite, you’ll be on a hiking trail that will take you to Race Brook Falls and the Appalachian Trail. Get a head start by booking the four-bedroom villa, the Race Mountain House, higher up on the slope. Cathedral-high ceilings fill with a warm sunrise glow, inviting you to get up and out into nature. Start the morning with coffee on the screened porch, then mix a drink for starlit sipping on the deck.

The art aficionados among you will dig Hotel on North. The contemporary culture and storied history of Pittsfield, Massachusetts, lend this hotel a personality as authentic and juxtaposed as the city itself. Your first stop should be the Gallery: a curated collection of sculptures, photography and art right beside the lobby. After appreciating the best of the Berkshires in the rotating exhibit, head into town to the Lichtenstein Center for the Arts and the Whitney Center for the Arts.

Shutterbugs should definitely pack a few different lenses for their stay at Seven Hills Inn. The gargantuan chess board on the back lawn, crackling fire on the bluestone patio and 27 acres (11ha) of lush gardens offer ample opportunity to refocus. Ready your camera and head down wooded lanes in search of the perfect shot that captures the beauty and serenity of the Berkshires. Put the lens cap back on when you arrive back at your stylish suite; the cozy fireplace and generous windows facing the tree-lined grounds are sights you’ll want to keep all to yourself.

Wellness is the priority at this 600-acre (243ha) holistic retreat. Meditation rooms, yoga studios and tranquil green spaces will all help you find your zen. Complimentary classes such as martial arts and cooking are available as well. Trade the typical facials and manicures for Healing Arts spa services, which include an energy healing massage, self-awareness through astrology, and chi balancing sessions. It’s a safe bet that by the time you check out, your body, mind and spirit will feel completely rejuvenated.

Those who appreciate the finer things in life will find a luxurious private sanctuary at Wheatleigh. A secluded outdoor pool and large soaking tub in each suite will tempt you to float your worries away throughout the day. Reservations are a must at the intimate Portico by Jeffrey Thomson, where you’ll dine on a multi-course French menu accompanied by handpicked bottles from the wine cellar. Should you need anything during your stay, the exceptional team here is ready to tend to your every need at the lift of a finger.

Foodies, prepare for a weekend full of fresh delights when you visit this strikingly preserved barn. It once housed the finest Jersey cattle of the Gilded Age, and has since been masterfully renovated to provide you with large tiled whirlpool tubs and granite fireplaces. However, you might as well call the Gedney Kitchen your suite; you’ll want to spend all of your time sampling more than 50 wines while dining on littleneck clams, grilled tivoli mushrooms and roasted duck breast. Walk off each meal around the 200-acre (81ha) grounds.

Bring along your four-legged friends when you stay at the Williams Inn. The farmhouse-style guestrooms provide plenty of room for your pets to stretch their paws. We suggest booking a king room with oversized chairs so you don’t have to share the bed. Ready the leash and take a nice walk through Williams to Linear Park or Denison Park. If your dog desires a little more room to explore, Hopkins Memorial Forest is only a five-minute drive away.