Where to Stay in the Berkshires, Massachusetts

The Berkshires in Massachusetts wows travelers with evocative autumnal landscapes
The Berkshires in Massachusetts wows travelers with evocative autumnal landscapes | © Hemis / Alamy Stock Photo
Ali Ray

From country homes on the National Register of Historic Places to 19th-century mill workers’ cottages, here’s where you should stay on vacation in the Berkshires, Massachusetts – and they’re all bookable with Culture Trip.

An historically feted destination for discerning Bostonians and New Yorkers, the Berkshires epitomize the Golden Age of weekend breaks – when rich industrialists left the cities to build their grand mansions in the mountains. Most of those opulent dwellings have since been converted into sumptuous hotels, offering tantalizing glimpses into how the American aristocracy once lived. Choosing the right one for your getaway, however, is no mean feat – thankfully, we’re here to help, with our pick of the poshest piles.

1. Blantyre


Courtesy of Blantyre / Expedia

Guests at baronial-style Blantyre will get a taste, quite literally, for that gilded-age lifestyle. Enjoy lobster picnics on manicured lawns, sipping vintage champagne in the jewel box-like Dom Perignon Salon or basking in the glow of the ornate fireplace while chandeliers glitter overhead. When it’s time to dine, sweep down the grand staircase and wait to be ushered to your table at chef Daniel Boulod’s restaurant, where you’ll be treated to a celebration of locally sourced ingredients.

2. Wheatleigh


Courtesy of Wheatleigh / Expedia

The design of this sprawling country home, listed on the National Register of Historic Places, was inspired by the original owner’s ancestral home in Oxford, England. Expect antique furnishings and museum-quality artworks adorning your bedroom wall. But beyond the history, it’s the tasting menu at the intimate, eight-table hotel restaurant that draws returning guests. Allow your taste buds to be taken on a tour of the best produce in the state, with dishes such as Arctic char, crab, and wagyu beef tartare with watermelon radish.

3. Cranwell Spa and Golf Resort

Hotel, Resort

USA, New England, Massachusetts, Lee, Golf Course at Cranwell Resort & Spa,
© Prisma by Dukas Presseagentur GmbH / Alamy Stock Photo

You’re spoiled for choice when it comes to room type at this showstopper of a resort. Want contemporary elegance? Book yourself into the main Tudor-style mansion. For privacy – and antique-y, turn-of-the-century charm – opt for one of the family-friendly cottages (with kitchenettes) in the grounds. Either way, the cozy 1894 Fireside Bistro and Bar is the place to meet up with locals and other guests, and clink glasses of craft ale.

4. Canyon Ranch Lenox

Hotel, Resort

Beauty farm Canyon Ranch, Lenox, Berkshire Hills, Massachusetts, USA, United States of America
© imagebroker / Alamy Stock Photo

In truth, the word ranch belies the opulence that awaits at this refurbed mansion in Lenox. This exceptional, all-inclusive wellness resort offers a curated New Experience Pathway package, which consists of a bespoke combination of up to 35 daily activities – from yoga and creative art classes, to shinrin yoku (forest bathing) sessions and consultations with physicians and dieticians. If you fancy starting your day snow-shoeing at sunrise in the mountains and ending it with a sunset canoe on the lake, this one is for you.

5. The Williams Inn

Hotel, Inn

The Williams Inn
Courtesy of the Williams Inn / Expedia

Immerse yourself in local life with a stay in this contemporary three-story inn in the heart of Williamstown. It’s just a short stroll from Williams College where you’ll find theaters, museums and galleries. Rooms feature native Berkshire stone and timbers, creating a modern farmhouse-chic vibe – an aesthetic echoed on the menu at the in-house Barn Kitchen & Bar, a delight of seasonal ingredients from named local producers. The charcuterie board, with the best artisan cheeses and cured meats in the area, is a must.

6. Porches Inn


Porches Inn
Courtesy of Porches Inn / Expedia

If you are looking to connect with local life in the charming Mill Town of North Adams, you’ll find a real home-from-home at the Porches – a row of beautifully converted 19th-century mill workers’ cottages. Each room is unique; some have spiral staircases and clawfoot tubs, while others have kitchens and cozy reading chairs. All have rich colors and materials – think leathers, velvets and natural wood. The Massachusetts Museum of Contemporary Art (MASS MoCA), just steps away from the front door, offers an intro to the local art scene.

7. Kemble Inn


Kemble Inn
Courtesy of Kemble Inn / Expedia

An exquisitely revitalized turn-of-the century mansion, Kemble Inn has just nine guest rooms, making a stay feel more like a sleep over at a (very well-off) friend’s country pile. And you’re encouraged to treat it so – sip cocktails on the sprawling back lawn, chill out in the comfy reading chairs in the lounge, play chess, Scrabble or tinkle the ivories at the piano. Dinner is served around a dining table large enough for all guests – a proper family-style affair.

8. Seven Hills Inn


Seven Hills Inn
Courtesy of Seven Hills Inn / Expedia

Culture vultures will love the Seven Hills Inn. This stylishly renovated boutique hotel is right next door to the Mount, part of Pulitzer Prize-winning author Edith Wharton’s estate, which is open for guided tours and exhibitions. A Shakespeare theater and dance company are a short drive away, as is a museum dedicated to ex-resident artist Norman Rockwell. Or, just stay put and enjoy the 27 acres (10ha) of lush landscaped gardens at the hotel.

9. The Inn at Stockbridge

Hotel, Inn

The Inn at Stockbridge
Courtesy of the Inn at Stockbridge / Expedia

This is the place for lovers of the outdoors with a penchant for colonial white clapboard charm. Exemplary friendly service and a delicious home-cooked breakfast (pumpkin pancakes, anyone?) will set you up for a day hiking to the waterfalls in Bash Bish Falls Park or along the Appalachian Trail. But get back in time for happy hour – a reception of complimentary wine, local cheeses and quiet jazz served on the back deck.

10. The Cornell Inn, Lenox

Bed and Breakfast, Inn

The Cornell Inn, Lenox
Courtesy of the Cornell Inn, Lenox / Expedia

In the heart of the historic village of Lenox, surrounded by restaurants, museums, shops and galleries, the Cornell Inn is a prime cut of real estate. It’s also just five minutes from the music venue Tanglewood, the summer home of the Boston Symphony Orchestra. Even better, as a guest, you’ll get discounts on tickets. This 28-room B&B is set across three beautiful New England-style 18th- and 19th-century buildings, with each room featuring wood-burning fireplaces.

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