The Best Boutique Hotels in the Berkshires, Massachusetts

The 12 Best Boutique Hotels in the Berkshires, Massachusetts

Located in western Massachusetts, the Berkshires region has long been a place filled with culture, history, and adventure. Some of the greatest thinkers and creators in American history have called this region home, like Edith Wharton, the writer whose home can be toured in Lenox, and Norman Rockwell, the illustrator whose studio and work is on display in Stockbridge.

The Berkshires are filled with quintessential New England towns, each with their own personality. Over in North Adams, you’ll find a vibrant art community. Meanwhile, you can hit the slopes in Hancock. Throughout the many towns, you’ll find theaters, museums, fine dining, boutique shopping, and historical landmarks galore.

Planning a trip to the Berkshires and wondering where to stay? We’ve compiled a list of the best hotels in the Berkshires, from charming inns to opulent mansions. Pick your favorite hotel from this list, and you’re bound to have an incredible time on your getaway to the Northeast.

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Where to Stay in the Berkshires

Where to Stay in the Berkshires, Massachusetts: Best Boutique Hotels

The beauty of visiting the Berkshires is there are so many unique towns that make up the region. It’s difficult to say just where the best place to stay in the Berkshires is because each town offers something a little different. 

If you’re looking for all the biggest attractions in the Berkshires, you should most likely look for accommodations in Lenox. The charming town of Lenox is the cultural heart of the region. Here, you’ll find Tanglewood, the summer home of the Boston Symphony Orchestra, as well as many other historic landmarks, museums, boutique shops, and fine dining establishments.

For a lot of culture but a more small-town feel, try Stockbridge. With its charming Main Street, there’s just something cozy and comfortable about staying in this village. And you’ll still have your pick of museums and historic places to explore.

But if you’d rather be closer to nature and a bit removed from the rest of the world, Great Barrington has what you’re looking for. However, you shouldn’t forget about the quaint town of Lee. You’ll be within driving distance of many of the top attractions in the Berkshires. Plus, Lee is home to a number of excellent hotels. 

The 12 Best Hotels in the Berkshires, MA

1. Devonfield Inn

Best Hotels in Berkshires, Massachusetts: Devonfield Inn
Photos: Devonfield Inn

Situated on 32 beautifully maintained acres in Lee, Devonfield Inn is one of the best places to stay in the Berkshires if you’re looking for luxury and romance. This historic bed-and-breakfast dates back to the 1800s and offers timeless decor among more modern amenities.

All rooms come with private bathrooms, air-conditioning, smart TVs, free Wi-Fi, and pillowtop mattresses. Upgraded rooms also come with fireplaces and whirlpool baths. This inn goes the extra mile by offering many complimentary touches, and all guests are welcomed with bottled water and locally-made chocolates! 

This B&B is primarily an adults-only location that’s best for romantic getaways. As such, young children are not permitted. Only children over 10 are welcome. Small pets are always welcome to stay for a nightly fee in case you want to bring your furry friend along.

In the morning, you’ll greet the day with local coffee and a full breakfast, complete with a cold buffet and a choice of two hot entrees, in the formal dining room. The breakfast is made up of locally grown ingredients, including herbs and vegetables grown right on-site.

Throughout the day, more complimentary gifts are available to you, like cognac and cordials in the living room, which is complete with a baby grand piano, library, and wood-burning fireplace. There’s also a fully stocked guest pantry, where you’ll find coffee, tea, hot chocolate, and freshly baked cookies. Also on-site is a sitting room, seasonal sunroom, heated outdoor pool, hiking trails, and tennis courts.

2. The Constance

Berkshires Boutique Hotels: The Constance
Photos: The Constance

Located in Lenox, The Constance is one of the most charming boutique hotels in the Berkshires, set in a stunning Victorian mansion. This place exudes elegance with every touch, from the turrets to the gardens. There’s history all around you when you stay at The Constance, as it’s been serving the area since 1825, when it was initially built as a tavern.

Staying here gets you access to free Wi-Fi and parking. Guest rooms come with private bathrooms and flat-screen TVs with Apple TV. But all rooms are individually decorated and come with their own set of amenities, like clawfoot tubs, fireplaces, or garden views.   

Start the day with a continental breakfast in the dining room or on the veranda. And after you’re done exploring the beauty of the Berkshires, come home to the warmth of the fire in the antique-filled lounge or curl up with a good book in the sitting room. 

3. The Cornell Inn

Best Hotels in Berkshires, Massachusetts: The Cornell Inn
Photos: The Cornell Inn

Another Lenox find, The Cornell Inn, is a charming bed-and-breakfast set on four beautifully landscaped acres, offering you tranquility during your stay. Guest rooms and common areas are spread across three 18th- and 19th-century buildings, but they’ve been renovated to maintain their historic integrity while offering more modern conveniences.

This Berkshires boutique hotel has uniquely decorated guest rooms that all have something a little different to offer. All rooms come with private bathrooms, TVs with cable, free Wi-Fi, and coffee makers. However, many rooms come with additional touches like fireplaces, trundle beds, private or shared balconies, or kitchenettes.

As a bed-and-breakfast, food is also at the heart of the hotel. In the morning, you’ll get a made-to-order breakfast filled with locally-made ingredients. 

But the treats don’t stop there! From in-room wine to espresso drinks to a goodnight glass of cognac to fresh brownies available at all hours of the day, it’s all on the house. While there are both complimentary non-alcoholic and alcoholic drinks available throughout the day, you can also grab a cocktail at The Tavern, the on-site bar and lounge.

4. Lakehouse Inn

Cool Berkshires Hotels: Lakehouse Inn
Photos: Lakehouse Inn

Set in Lee and situated on the beautiful Laurel Lake, the Lakehouse Inn is The Cornell Inn’s sister property and is another one of the best boutique hotels in the Berkshires. Like its sister hotel, the Lakehouse Inn is all about going beyond the expected, offering touches that will make your stay memorable and luxurious.

All rooms feature upscale amenities like towel warmers, flat-screen TVs, coffee makers, beach towels, individual climate control, and complimentary Wi-Fi and parking. Some rooms have sleeper sofas, while suites add a living room area. Select rooms feature garden views, lake views, or balconies.

Only guests staying at the Lakehouse Inn can use the lake, which means that you get a beautiful, pristine lake nearly all to yourself during your stay. Guests are allowed to swim, kayak, paddleboard, and fish in the lake, provided they have a Massachusetts fishing license. 

If you don’t have your own paddleboard or kayak, you can rent them for free from the inn, as they are available on a first-come, first-served basis. Or you can just relax by the seasonal gas fire pit.

Like The Cornell, food and drink are what this Berkshires hotel does particularly well. A free seasonal welcome drink will greet you upon your arrival, and there’s a free bottle of wine waiting for you in your guest room. 

In the morning, you’ll start each day with a gourmet, sit-down breakfast in the dining room. And you’ll end each day with a complimentary glass of cognac. In between, brownies, pastries, and tea are available for free all day long, as well as homemade ice cream in the summer!

5. Wheatleigh

Cool Hotels in Berkshires, Massachusetts: Wheatleigh
Photos: Wheatleigh

When you stay at the Wheatleigh, one of the coolest Berkshires hotels, you’ll get the royal treatment. Set in an 1893 Italianate mansion nestled on 22 acres in Lenox, this one-of-a-kind hotel is filled with Gilded Age splendor. Once you see the grounds, you’ll surely understand why the Wheatleigh earned its spot on the National Register of Historic Places.

The sophisticated guest rooms in this luxurious chateau feature fine antiques, museum-quality artwork, antique soaking tubs, separate showers, smart TVs with Roku, free Wi-Fi, a Bose sound system, and a subscription to the New York Times Unlimited. Many rooms also feature fireplaces and courtyard views. 

Work out in the fitness center, take a dip in the seasonal outdoor pool, play a round of tennis, or get a relaxing massage. Indulge in a wine tasting, or enjoy a dinner at The Bistro, the Wheatleigh’s award-winning on-site restaurant.

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6. Shaker Mill Inn

Cool Berkshires Hotels: Shaker Mill Inn
Photos: Shaker Mill Inn

While many of the best Berkshires hotels focus on upping the romance, the Shaker Mill Inn differentiates itself by being a place for family. Even your furry family members are invited to stay for a small added fee!

Unlike other bed-and-breakfasts in the Berkshires, breakfast time is up to you. Every room in the hotel has a fully equipped kitchenette, except the Greylock Suite, which has a full kitchen. Upon your arrival, your room will be stocked with breakfast foods, from pastries to quiches. You can enjoy breakfast any time in the privacy of your own room. And if you run out, you can request more at no extra charge.

Each suite at this inn in West Stockbridge offers something a little different so you can tailor your stay to your family’s needs. While all rooms have private entrances and free Wi-Fi, other amenities provided throughout the hotel include satellite TV, air-conditioning, phone charging stations, sleeper sofas, fireplaces, and two-person Jacuzzi tubs, depending on the room. 

7. Hampton Terrace Inn

Cool Hotels in Berkshires, Massachusetts: Hampton Terrace Inn
Photos: Hampton Terrace Inn

Set in a historic mansion dating back to 1897 in Lenox, the Hampton Terrace Inn is one of the best hotels in the Berkshires if you’re looking for luxury. This Berkshires boutique hotel strives to be a testament to the Gilded Age, with all its beauty and glamour. But among the timeless decor, you’ll find many more modern conveniences.

All Victorian-style guest rooms come with private baths, air-conditioning, HDTVs, and free Wi-Fi. Upgraded rooms come with additional touches like four-poster beds, fireplaces, and Jacuzzis. While this romantic inn is a perfect choice for a couple’s getaway, families are welcome, provided that all children are over the age of 10.

This bed-and-breakfast offers many touches that are bound to make your stay even better. There’s plenty on the house for you to enjoy, including complimentary liqueurs, water bottles, and coffee. 

Each day, you’ll wake up to a full breakfast buffet. If you have your own food, you can store it in the guest fridges and use their family heirloom bar for all the plates, silverware, and other tools you need to enjoy a meal. 

Tickle the ivories on the 1929 Steinway grand piano and enjoy the company of your fellow guests in the lounge. Or take a dip in the seasonal heated outdoor pool.

8. Granville House

Unique Berkshires Hotels: Granville House
Photos: Granville House

Located in Great Barrington, the Granville House is a country getaway and one of the best boutique hotels in the Berkshires. This historic house has been a part of the Berkshires since 1825, with its owners playing essential roles in shaping the area’s history. Today, it’s a family-owned bed-and-breakfast created by a couple who believes in providing personal and professional service.

This property is a small and intimate one. Having only five rooms, the owners are able to create more personalized experiences for their guests. 

Although each room has its own individual design and decor, all rooms have Brooklinen bedding, complimentary MALIN+GOETZ bath products, private baths, mini-fridges, Keurig coffee makers, and Crosley record players. Some rooms feature additional touches like reading nooks, writing desks, pullout couches, and soaking tubs.

You can find records to play in the inn’s extensive vinyl collection. There’s also a large library of books, puzzles, and board games.

Furry family members are invited to stay with you, with the exception of not being allowed in the dining room. Additionally, this Berkshires hotel is primarily an adults-centered one. Children are allowed to stay as long as they’re over the age of 10. 

Each morning, you’ll greet the day with a made-to-order breakfast. From there, you can head out and enjoy the Berkshires or spend the day in the inn. 

Curl up by the fire in the front sitting room, play pool in the parlor, or listen to records in the music room. Take in the morning air from a rocking chair on the wraparound porch. Then, end the day roasting marshmallows in the backyard fire pit! 

9. Brook Farm Inn

Unique Hotels in Berkshires, Massachusetts: Brook Farm Inn
Photos: Brook Farm Inn

Over in Lenox is one of the most unique hotels in the Berkshires. Brook Farm Inn offers a little something for everyone. It’s rustic and rural while also being upscale and elegant. You’re just a short walk to downtown, but with its serene gardens all around the house, you’ll feel like you’re miles away from the world. 

Built in 1882, this Berkshires boutique hotel strives to keep its old-world charm. The individually decorated guest rooms have private bathrooms and free Wi-Fi. Amenities vary by room and may include flat-screen TVs with cable, sitting areas, or fireplaces. Upgraded rooms and suites offer even more, including Keurig coffee makers, mini-fridges, sofa beds, or hot tubs. 

Each morning, you’ll start off with a full breakfast before heading out to explore the beauty of the Berkshires. When the weather’s cold, you can curl up by the fire in the communal living room or read a good book in the library. But when the weather heats up, you can take a dip in the seasonal heated outdoor pool. 

10. 33 Main

Berkshires Boutique Hotels: 33 Main
Photos: 33 Main

33 Main is one of the coolest Berkshires hotels because it feels like home – that is, if your home offers luxurious amenities, of course. Located in Lenox, this bed-and-breakfast was created and curated by a Lenox resident who put together her years of travel to make the best hotel she could imagine. 

This beautiful Federal-style home dates back to 1836, but it’s received several renovations to turn it into the bed-and-breakfast it is today while still keeping its historic charm. Each room is uniquely decorated and offers its own set of amenities, but all rooms provide a private bath, bathrobes, complimentary vegan toiletries, free Wi-Fi, and smart TVs with Netflix and Hulu access. 

This hotel is strictly adults-only. All guests must be over the age of 21. Select rooms are pet-friendly. Pets also get treated to their own luxurious getaway, with amenities including their own personal WOUF, a cozy place for them to lounge!

Breakfast is on the house, as is a welcome gift of freshly baked cookies and bottled water. And in the evenings, you can enjoy a complimentary cocktail hour in the front parlor.

11. Chambery Inn

Best Hotels in Berkshires, Massachusetts: Chambery Inn
Photos: Chambery Inn

Set in a former schoolhouse that dates back to 1885, the Chambery Inn is one of the most unique hotels in the Berkshires. This historic bed-and-breakfast in Lee makes you feel like you’re stepping back in time.

This Berkshires boutique hotel features French-inspired decor and unique touches like high ceilings and 19th-century blackboards. Guest rooms include canopy beds, free Wi-Fi, free parking, smart TVs, Alexa-enabled alarm clocks, and coffee and tea stations. Many rooms contain additional touches like sitting areas, fireplaces, or jetted tubs.

Unlike other bed-and-breakfasts, you don’t have to gather in a specific room or eat at a designated time. Instead, you simply order your breakfast to be delivered to your room. Select the options you want on a card and what time you want them, then hang it on the door. 

You’ll get a breakfast basket delivered to your door so you can enjoy breakfast in bed every day! A snack bar is also available on-site for more treats. 

12. Wainwright Inn

Where to Stay in Berkshires, Massachusetts: Wainwright Inn
Photos: Wainwright Inn

Located on an 18th-century estate in Great Barrington, Wainwright Inn is a warm and cozy bed-and-breakfast and another one of the best boutique hotels in the Berkshires. This historic home has a very unique past, as it served as a fort and colonial armory during the American Revolution.

Rooms are separated between the Main House and the Carriage House. If you’re staying in the Carriage House, you get access to everything in the Main House, as well as a shared deck and kitchenette. All rooms come with private baths, TVs, free Wi-Fi, ceiling fans, air-conditioning, and complimentary toiletries.

Keep in mind that this historic estate does not have an elevator. Book a room on the first floor if you have trouble getting up and down stairs.

Enjoy a homecooked breakfast each morning in the Main House in the sun-filled dining room or on the porch if the weather’s nice. But if it’s chilly, hang out in the communal living room, where you can warm up by the fire.

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There you have it! The 12 best hotels in the Berkshires. What’s your favorite place to stay in the Berkshires? Let us know in the comments!

Planning a trip to Massachusetts? Check out our favorite books and travel guides!



  • Jacqueline Gualtieri

    Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California.

    When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes.

    Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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