8 Luxury Hotels in the Berkshires

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With gentle peaks, fairytale-like forests, idyllic meadows, and subtle New England charms, the Berkshires are among the most treasured outdoor playgrounds in Massachusetts. Elevations here never reach more than 900 feet, and the area is fewer than 100 miles.

Modest stats don’t stop these highlands from being one of the most beloved American recreational places. It is here that “Moby Dick” writer Herman Melville lived and created, it is here that you find such iconic performance venues as Tanglewood and Jacob’s Pillow, and it is here that the celebrated painter Norman Rockwell spent more than 20 years of his life.

No wonder such an inspiring region has such fantastic lodging. Here are the best luxury hotels in the Berkshires that will allow you to feel the magnetic atmosphere of these hills.

Wheatleigh - Lenox
Wheatleigh - Lenox

Wheatleigh - Lenox

Wheatleigh is the epitome of luxury. One of the best luxury hotels in the Berkshires, it is a tasteful affair. Originally built as an Italian-inspired country home in 1893, it has been subsequently turned into a deluxe accommodation. A curious fact is that the building is included in the National Register of Historic Places, so you’ll be literally surrounded by history. There are only 19 guest rooms and suites, but how beautiful is this place?! You will be treated to magnificent Gilded Age interiors, carefully curated furniture, and lots of art around the premises. It’s at this kind of property that you will feel the magic of the Berkshires, especially if you’re around to see the incredible New England fall foliage. Outside you’ll find the palatial gardens for the ultimate contemplative moment. You will also have the premium on-site establishment called The Portico by Jeffery Thomson, which serves modern interpretations of French cuisine.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires - Great Barrington
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires - Great Barrington

Choose Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires for a smart luxury hotel in the Berkshires. Located in Great Barrington, one of the gateways to the highlands and one of Massachusetts’ best places to visit, this hotel would be a perfect base for exploring the region. Of course, any base should provide the maximum level of comfort, and that’s exactly what you’re getting here. Breakfast comes very highly regarded by guests in reviews, as does the impeccable cleanliness of the property. The indoor heated pool with a whirlpool also proves to be a popular amenity. The suites boast modern designs and come with free WiFi, flat-screen TVs, and premium bedding. Be sure to check out the colorful downtown of Great Barrington with its cozy cafes inside old brick houses.

Courtyard Lenox Berkshires - Lenox
Courtyard by Marriott Lenox Berkshires

Courtyard Lenox Berkshires - Lenox

Being in the Berkshires feels awesome at the Courtyard Lenox Berkshires hotel. You’re surrounded by the forest, the rooms overlook the greenery, and all the area’s must-visit attractions are a short drive away. The exterior of this hotel is reminiscent of a French chateau, while the insides are very contemporary and delightful to be around. Expect sparklingly clean and comfy rooms with 40-inch flat-panel TVs, mini-refrigerators, and top-quality beds. Booking a slick studio with two queen beds would be the best idea for maximum comfort. While in Lenox, one of Massachusetts’ most charming small towns, you can’t miss the Shakespeare & Company theatre group (Andie MacDowell, Keanu Reeves, and Sigourney Weaver are alums) and Tanglewood, a celebrated venue and the summer home of the Boston Symphony Orchestra. 

The Barrington - Great Barrington
The Barrington

The Barrington - Great Barrington

For centuries, the Berkshires have drawn the wealthy and famous with its charms, and The Barrington joins that charm. Towns of the region are characterized by gorgeous colonial mansions that greet travelers with intricate architecture and wide porches. Today, many of these are luxury boutique hotels. The Barrington is one such property. Always delivering on its promise of the Old World ambiance, this lovely hotel boasts a variety of named suites, each sporting a different decor. Their similarity is in devotion to guests’ comfort and top-notch amenities. Staying in such accommodation is a very intimate, personalized way to have a luxury hotel experience in the Berkshires.

Hotel on North - Pittsfield
Hotel on North - Pittsfield

Hotel on North - Pittsfield

While a typical Berkshire experience usually involves exploring the hilly countryside, the region is also famous for its creative and quaint towns like Pittsfield, the capital of Berkshires country. It is here that you find one of the most incredible luxury hotels in the region, the Hotel on North. Attention to detail, respect for the past, and a talented reinterpretation of designs in the present define this upscale central lodging. Their approach is full of enthusiasm and love, with each room and suite boasting special character. For uncondensed historic chic, check out the 644-square-foot Library Suite with 125 bookshelves, a wet bar, and a claw-foot tub. The Hotel on North is for an urban Berkshires retreat. Barrington Stage Company, host of plenty of great performances, is right around the corner and you’ve got a myriad of dining choices on North Street, as well as Herman Melville’s Arrowhead just a few miles away by car.

The Williams Inn - Williamstown
The Williams Inn - Williamstown

The Williams Inn - Williamstown

People love The Williams Inn. Combining rustic looks inspired by the farmhouses of the area with the chic of an upmarket lodging, it’s steadily getting ultra-positive reviews from the guests. The delightful atmosphere, well-decorated rooms, modern amenities, and friendliness of the staff are among this hotel’s fortes, according to prior guests. Indeed, the accommodation takes design seriously, providing slick interiors filled with curated furniture that both echo and enhance the surrounding Berkshire landscapes. The on-site restaurant The Barn is where you can try the local food prepared with seasonal ingredients. Williamstown’s location means that you’re at the access point to the Mount Greylock State Reservation, which has lots of hiking trails that lead straight to the highest point in Massachusetts.

The Inn at Stockbridge - Stockbridge
The Inn at Stockbridge

The Inn at Stockbridge - Stockbridge

Become a heroine (or a hero) of a New England romance at The Inn at Stockbridge. You will stay in a beautifully-renovated 1906 Georgian mansion surrounded by landscaped gardens. Take just a few steps inside its grounds, and you’ll find a backyard pool area, a charming addition to your Berkshires getaway. Choosing a historic inn hotel is the way this region is meant to be savored. There are suites with fireplaces and whirlpool hot tubs. That’s the one to opt for if your goal is a full-scale Berkshires repose. The remote location outside Stockbridge adds to the feeling of privacy, and you’re still very close to all the attractions that make this region famous, like the Naumkeag Museum, Norman Rockwell Museum, and The Mount (Edith Wharton’s Home).

The Black Swan Lee, Ascend Hotel Collection - Lee
The Black Swan Lee, Ascend Hotel Collection

The Black Swan Lee, Ascend Hotel Collection - Lee

Staying at a luxurious lakeside accommodation is always a dreamy experience. The Black Swan Lee is that property in the Berkshires. The location is a part of the deluxe offerings here, while the rooms come with views of the water that will certainly catch your attention. What is a better mountain escape than waking up to the panoramas of the lake surrounded by the forests and the hills of the Berkshires? Here you can fully embrace being in nature. Also, the location between Lee and Lenox allows for effortless exploration of the region.

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