The Best Hotels to Book in the Berkshires, Massachusetts

Berkshires hotels such as Wheatleigh offer relaxation, luxury and delicious food in a lush setting
Berkshires hotels such as Wheatleigh offer relaxation, luxury and delicious food in a lush setting | Courtesy of Wheatleigh / Expedia
Nick Dauk

When you envision the perfect Berkshires vacation, what comes to mind? Browsing handmade crafts at quaint village shops? Hiking and biking miles of mountain terrain? Or enjoying great grub with room service? Offering local cuisine, unspoilt mountainous backdrops and finest art in the region, these hotels in Massachusetts and Connecticut make it a reality – bookable on Culture Trip.

1. Blantyre


Courtesy of Blantyre / Expedia

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.

2. The Old Inn on the Green


The Old Inn on the Green
Courtesy of The Old Inn on the Green / Expedia

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.

3. The Red Lion Inn


The Red Lion Inn
Courtesy of The Red Lion Inn / Expedia

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.

4. Race Brook Lodge


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.

5. Hotel on North

Boutique Hotel

Hotel on North
Courtesy of Hotel on North / Expedia

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.

6. Seven Hills Inn


Seven Hills Inn
Courtesy of Seven Hills Inn / Expedia

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.

7. Eastover Estate & Eco-Village

Hotel, Eco Hotel

Eastover Estate & Eco-Village

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.

8. Wheatleigh


Courtesy of Wheatleigh / Expedia

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.

9. Gedney Farm


Gedney Farm
Courtesy of Gedney Farm / Expedia

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.

10. The Williams Inn

Hotel, Inn

The Williams Inn
Courtesy of the Williams Inn / Expedia

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.

For a unique stay, check out our pick of the most beautiful boutique hotels in Massachusetts, bookable on Culture Trip.

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