The 12 best hotels in the Berkshires, from cozy B&Bs to renovated Gilded Age mansions

February 25, 2021

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Easy access to nature and numerous cultural attractions make the Berkshires an enticing getaway.
From Williamstown to the shores of Lake Laurel, we rounded up the best hotels in the Berkshires.
Our top picks range from $130 to $239 per night, plus one splurge-worthy option for a truly special stay.

The Berkshires have long been a magnet for Northeast city dwellers craving an immersion in nature. During the Gilded Age, well-heeled visitors called it the Inland Newport and flocked here for the fresh country air and outdoor activities, just as travelers still do today.

These hills are also a haven for those who appreciate culture. Since the 19th century, it has been a favorite retreat for artists, musicians, and writers, who draw inspiration from the bucolic scenery. A patchwork of picturesque villages offer a springboard for a wealth of cultural attractions, from Tanglewood, the summer home of the Boston Symphony Orchestra, to Shakespeare & Company for lovers of the Bard. Noted art museums range from large-scale contemporary work at Mass MoCA to the nostalgic illustrations at the Norman Rockwell Museum. However, keep in mind that many area museums are presently open at reduced capacity.

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Additionally, to slow the spread of COVID-19, there are currently travel restrictions for visitors entering Massachusetts from high-risk states. The situation is fluid, so be sure to read up on the most current information.

It is equally important to note that there is no guarantee of safety when it comes to travel during the ongoing pandemic. We recommend following guidelines form the CDC, WHO, and other reputable organizations, as well as wearing a mask, washing your hands frequently, and maintaining social distancing.

That said, visiting the Berkshires is a particularly attractive option right now since it’s within an easy drive of many East Coast cities, and there’s plenty of space to roam and social distance.

We selected the best Berkshires hotels based on the following criteria:

All have COVID-19 safety precautions in place.
We’ve kept affordability at the forefront, with accommodations between $130 to $289 per night, plus one splurge.
I’ve stayed at many of these hotels myself, but all also have excellent ratings and reviews from Trip Advisor and Booking.com.
We’ve included a range of accommodations, from cozy B&Bs to opulent hotels in Gilded Age mansions.

Here are the best hotels in the Berkshires, sorted by price from low to high.

Hotel on North

Book Hotel on North starting from $130 per night

This boutique hotel is located in Pittsfield, a small city with cosmopolitan flavor and a rich arts and culture scene. The design team has maintained a commitment to historic preservation, modernizing two 19th century retail buildings while keeping original details like tin ceilings and quirky columns. These heritage nods blend with modern conveniences, satisfying your sense of style without sacrificing creature comforts.

The 45 guest rooms embrace a local artisan ethos. Hand-crafted wood furnishings are made in the Berkshires, the in-room coffee is roasted right in town, and local artwork hangs on the exposed brick walls. All rooms have flat-screen televisions, Bluetooth-enabled audio, and fiber-optic Wi-Fi. Some have gas fireplaces, kitchenettes, and washer/dryers. Bathrooms have separate showers or claw-foot soaking tubs. Perks include LATHER aromatherapy-based bath products and downy-soft Mascioni bed linens.

Trip Advisor Ranking: 2 out of 8 hotels in Pittsfield

Booking.com Rating: 9.2 out of 10

Pros: The art gallery adjacent to the lobby offers a rotating exhibit of paintings, sculptures, and photographs by area artists. Pets are welcome.

Cons: It’s in the heart of Pittsfield, so the setting is more urban than bucolic.

COVID-19 cleaning and safety procedures:

The restaurant is currently closed.
Daily housekeeping is suspended.
Hand sanitizer can be found in public spaces.
Masks are required to worn by the staff and guests.
Social distancing must be maintained.

The Black Swan

Book the Black Swan starting from $144 nightly

The Black Swan sits on the shores of Lake Laurel and at the foothills of October Mountain State Park. With a wealth of recreational options at your fingertips, plus fishing, swimming, and hiking on-site, it feels like a rustic resort. Take advantage of the location and relax in an Adirondack chair as you soak in the sparkling lake, or rent a kayak for an on-the-water experience.

Guest rooms are standard motel-style units that are simple but plenty comfortable. Some come with private balconies offering views of the lake. A desk, Wi-Fi, coffee makers, and a mini-fridge are practical and welcome amenities. Most guests come here to enjoy the outdoors, so chances are you won’t be spending much time in your room.

Mint, the on-site lakeside restaurant, serves authentic Indian cuisine.

Trip Advisor Ranking: 3 out of 9 hotels in Lee

Booking.com Rating: 8.5 out of 10

Pros: The lake setting is stunning and breakfast is included in the room rate.

Cons: If you’re looking for a guest room with bells and whistles, the simple accommodations will disappoint. The onsite Indian restaurant prepares its food spicy, so let your server know if you can’t take the heat.

COVID-19 cleaning and safety procedures:

Breakfast is served grab-and-go.
Enhanced and frequent cleaning of all public spaces.
Staff and guests must wear face masks.
The fitness room is closed until further notice.
Rental boats are cleaned between use.

The Porches Inn

Book The Porches Inn starting from $174 per night

An overnight stay at The Porches allows guests to dive into both history and culture. The hotel is located in North Adams, once a thriving manufacturing center. The 20th century brought factory closures, but North Adams managed to transform what could have been ruin into visual riches thanks to Mass MoCa. Housed in the former Sprague Electric factory, the museum is one of the most evocative centers of contemporary art in the world.

The Porches is set in seven renovated Victorian-era buildings that originally provided housing for mill workers. Rooms have access to a long porch and rocking chairs with views of MASS MoCA across the street.

The inn’s quirky collection of American antiques complements a clever synthesis of retro and contemporary designs. Decor intentionally blends old and new with a touch of ironic whimsy that might best be described as “granny chic.” Architectural framings and angles vary, with no two rooms alike. Some have private porches, lofts, fireplaces, and spiral staircases. Industrial architecture mingles with modern technology including fast Wi-Fi and Apple TVs. Unusual decorative notes include framed paint-by-number pictures, vintage TV lamps, and quirky collectible plates. Heated slate-floors in the bathroom, comfy oversized sofas, and a rich palette of color add atmosphere.

Trip Advisor Ranking: 1 of 3 hotels in North Adams

Booking.com Rating: 9.0 out of 10

Pros: The outdoor lap pool has a heated stone deck and is open year-round. An amped-up continental breakfast is included in the rate.

Cons: Some guests report in-room noise.

COVID-19 cleaning and safety procedures:

Increased cleaning and sanitizing in all public spaces.
Breakfast is now served in grab-and-go boxes.
Pool seating is configured to allow for at least six feet of separation between guests.
All employees receive training on COVID-19 safety protocol.
Hand sanitizer dispensers, touchless whenever possible, can be found around the hotel.
Masks will be worn by all employees at all times.
Guests are asked to use hand sanitizer and to wear a mask, provided by the property.
The sauna and hot tub are closed.

The Williams Inn

Book the Williams Inn starting at $179 per night

Home to Williams College and a world-class French Impressionist collection of paintings at the Clark Art Institute, Williamstown is a New England classic.

Built of stone and wood, the Williams Inn is reminiscent of a New England farmhouse. The farmhouse theme carries over into the guest rooms, with reclaimed barn doors and spare Shaker-style furniture, elegant in its simplicity. It’s all accentuated by natural light flooding in from the ample windows. There are dashes of color, including buttery yellows and smoky greys, but always in a soothing palette. Beds feature Euro-top mattresses and quality linens. Vaulted ceilings give a sense of space while a compact in-room fridge and excellent Wi-Fi add sensible notes.

Trip Advisor Ranking: 8 out of 15 hotels in Williamstown

Booking.com Rating: 9.4 out of 10

Pros: After a top-to-bottom recent renovation, the hotel is in excellent shape. The New England vibe is just enough without going overboard.

Cons: Some guests complain that the youthful staff could use additional training.

COVID-19 cleaning and safety procedures:

Masks are worn by all employees at all times.
Guests must comply with mask-wearing and social distancing.
Cleaning and sanitizing have been increased in all public spaces.
Guest rooms and common areas are cleaned using bacteria-killing ingredients in accordance with CDC guidelines.
The on-site restaurant is currently open for dinner only, Wednesday-Sunday evenings from 4 to 8 p.m.

Briarcliff Motel

Book the Briarcliff Motel starting at $180 per night

The Briarcliff Motel is a renovated 1960s motor lodge with retro flair. You’ll drive your car straight to the door of your room so it harkens back to the days of the great American road trip, which is seeing a revival amidst the pandemic. There’s a grassy lawn with a vegetable garden, firepit, volleyball net, and picnic tables for enjoying the outdoors.

Guest rooms are anything but cookie-cutter. Plush-top mattress and pure cotton linens make for a cozy bed setup, while bright red headboards and playful Marimekko floral and polka dot bedspreads in saturated shades of blue and red add a punch of color and personality. Vintage tiles and fixtures in the bathrooms add to the nostalgic vibe. Each has plenty of practical comforts too, such as a mini-fridge, flat-screen television, and high-speed internet.

The property is just across the road from towering Monument Mountain, where you’ll find the trailhead to hikes with stunning views of the valley.

Trip Advisor Ranking: 2 out of 10 hotels in Great Barrington

Booking.com Rating: 8.6 out of 10

Pros: The Briarcliff enjoys a tranquil location just a five-minute drive from the center of both Stockbridge and Great Barrington. The outdoor space is especially great for families.

Cons: There’s no on-site restaurant, though a simple Continental breakfast is served.

COVID-19 cleaning and safety procedures:

Guests will receive a door code to their room for contactless check-in.
You walk straight from your car to your room, a plus during the pandemic.
Breakfast is not currently being served. Instead, guests receive a $12 per person, per day voucher to dine at the Red Lion Inn, a 5-minute drive.
In-room housekeeping and high-touch areas are cleaned with great attention.
Daily housekeeping is unavailable at this time.
The lobby and firepit are closed.

The Red Lion Inn

Book the Red Lion Inn starting at $188 per night

The Red Lion Inn has been an anchor of Stockbridge since 1773, when it was born as a small tavern. It’s located in the middle of the idyllic village, walking distance from excellent dining and shopping.

Visitors step into the inn from the sweeping front porch with a cluster of old-fashioned rocking chairs and are greeted by the hotel’s collection of paintings, including works by Norman Rockwell, a plethora of antiques, and fine China mounted on the walls. Guests are given old-school room keys and may encounter a creaky staircase or two.

Lucky guests will catch a glimpse of the resident housecat curled up by the lobby’s wood-burning fireplace, and the sound of diners enjoying a hearty meal of folksy New England fare in the dining room adds to the homey vibe. Confident enough in its grandeur to embrace its eccentricities, it’s the Auntie Mame of Berkshire hotels.

Each room here has a distinct personality. Clawfoot tubs, braided rugs, floral wallpaper, and canopy beds exude traditional New England character while blending comforts like high-thread-count linens and fluffy bathrobes. The walls are decorated with timeless Toile de Jouy, a perfect foil for modern staples such as high-speed internet and plush mattresses.

Red Lion Inn’s newest annex, Maple Glen, provides an additional 17 guest rooms.

Trip Advisor Ranking: 1 out of 1 hotels in Stockbridge

Booking.com Rating: 8.6 out of 10

Pros: If you like historic hotels with Grande Dame style, it’s a slice of heaven. The dining room draws a loyal crowd who come to dine on creamy New England clam chowder and warm brown sugar cake.

Cons: Some guests report that the hotel is showing signs of its age, with rooms that are slightly frayed around the edges.

COVID-19 cleaning and safety procedures:

The hiring of a COVID Compliance Officer, with a background as a board-certified physician, who is informed on the latest public health advancements in order to advise on any necessary changes to the hotel’s protocols and procedures.
A partnership with Blue Canary, a company that trains hotels in hospital-level cleaning methods.
Employees receive training on COVID-19 sanitation protocols.
Hand sanitizer dispensers available in key areas around the hotel.
Appropriate PPE will be worn by all employees at all times.
Guests are asked to use hand sanitizer and to wear a mask, provided by the property in an amenity bag.
Reminders throughout the property on the proper way to wear, handle, and dispose of masks.

Seven Hills Inn

Book Seven Hills Inn Starting at $189 per night

This boutique hotel underwent extensive renovations just prior to the pandemic. The expansive bluestone patio is a lovely spot to soak in the property’s mature trees, lush lawns, and glorious gardens.

The centerpiece is a Gilded Age mansion that has been reimagined for today’s visitor. Guest rooms are found in three buildings, including the historic manor house. Decor leans modern, with clean lines and simple wood floors adding to the un-stuffy visual. Quality bed linens, mini-refrigerators, and Bigelow Apothecary bath and body products join the high-end furnishings. Modern amenities such as Bluetooth radios, USB plugs, and Wi-Fi keep things up-to-date. Rooms in the Carriage House have kitchenettes, while those in the Terrace House are particularly light and airy.

Have a dip in the seasonal outdoor pool and pedal around Lenox on loaner bikes.

Trip Advisor Ranking: 6 out of 18 hotels in Lenox

Booking.com Rating: 8.2 out of 10

Pros: It’s next door to The Mount, author Edith Wharton’s magnificent home and garden.

Cons: Some guests complain about a lack of staff.

COVID-19 cleaning and safety procedures:

Check-in available inside your car.
If you choose a traditional check-in, masked staff is behind a protective plexiglass shield.
Guest rooms are deep cleaned prior to guest arrival.
Hand sanitizer and wipes are available throughout the hotel.
Breakfast is served grab-and-go.
Check-out may be contactless via phone.

Gateways Inn

Book Gateways Inn starting at $209 per night

Gateways Inn is a romantic lodge in Lenox. Originally the summer home of Harley Proctor of the Proctor & Gamble family, there’s a relaxed feel, with hands-on innkeepers dedicated to perfecting the guest experience.

In a nod to the area’s literary legacy, each of the guestrooms is named after a Shakespearian heroine. Rooms are thoughtfully decorated with spindled sleigh beds, fireplaces, French doors, and marble sinks. In-room amenities include a mini-fridge and cable television, and fresh floral arrangements add a thoughtful touch.

In the common area, the grand foyer staircase has intricate woodwork that harks back to the affluence of the Gilded Age. The piano bar often draws a crowd thanks to live music and potent drinks, though it’s unfortunately currently closed due to COVID-19.

Trip Advisor Ranking: 3 out of 19 B&Bs in Lenox

Booking.com Rating: 9.2 out of 10

Pros: Friendly innkeepers offer a genuine welcome and the in-town location works well for those who want to explore without a car.

Cons: Some guests complain of spotty in-room Wi-Fi.

COVID-19 cleaning and safety procedures:

Breakfast service has been discontinued.
The bar and highly-rated restaurant are currently closed.
Contactless check-in and check-out.
48 hours of downtime between guests in each room.
Frequent cleaning with an emphasis on high-touch areas.
Mask must be worn by staff and guests.
Frequent handwashing for all employees.
Rooms are cleaned with electrostatic sanitation tactic prior to guest arrival.

Shaker Mill Inn

Book Shaker Mill Inn starting at $239 nightly

Social distancing comes easily at the Shaker Mill Inn, located in West Stockbridge. Rooms all have private entrances and there are no common gathering areas.

If you crave space, all guest rooms are suite-style. Units have wood floors, cheerful patchwork quilts, stone hearth fireplaces, and sleigh beds. Jacuzzi tubs and kitchenettes add to the amenities, while private decks, patios, and skylights add light. Suites all have satellite televisions, DVD players, and kitchens stocked with a variety of breakfast items to enjoy a morning meal in the safety and privacy of your room.

Trip Advisor Ranking: 1 out of 1 B&Bs in West Stockbridge

Booking.com Ranking: 9.2 out of 10

Pros: All units have kitchenettes, and several are pet-friendly. Each room also comes with a complimentary bottle of wine.

Cons: If you’d like someone else to prepare your morning meal, book elsewhere or stroll over to No. Six Depot for the Berkshire’s best cup of coffee.

COVID-19 cleaning and safety procedures:

Contactless check-in and check-out.
Enhanced room cleaning using products recommended by the state health department.
Proper social distancing is expected.
Masks must be worn by guests and staff.

The Inn at Stockbridge

Book the Inn at Stockbridge starting at $277 per night

The Inn at Stockbridge is a peaceful B&B nestled among acres of lush gardens growing flowers, herbs, and produce, with a seasonal outdoor heated pool dropped in for good measure. Housed in a 1906 Georgian-style mansion, the current innkeepers have restored it with great attention to detail and guest comfort.

The main house has eight traditional rooms with antique-style standing mirrors, four-poster beds, and gas fireplaces. Rooms feature floral wallpaper and curtains, but it’s sophisticated and won’t remind you of your grandma’s bedroom. Subtle accents of wicker and greenery bring the natural setting indoors.

Rooms in the Cottage House are light, airy, and dog-friendly, while rooms in The Barn are extra-spacious and work well for families. All rooms include CD players, sumptuous bathrobes, a mound of fluffy bed pillows, house-made room spray infused with essential oils, and Damana bath products enriched with herbal extracts.

A library, grand piano, game room, and extensive collection of vinyl can be found in the main house. Guests are encouraged to indulge in the daily wine and cheese reception on the wrap-around porch.

Trip Advisor Ranking: 1 out of 7 B&Bs in Stockbridge

Booking.com Rating: 9.6 out 10

Pros: Guests rave about breakfast, included in the rate. The innkeepers win accolades for service.

Cons: Some guests complain about noise in the main house due to thin walls.

COVID-19 cleaning and safety procedures:

Rooms are sanitized with a disinfectant fogger prior to check-in.
Rooms are cleaned only on request.
Breakfast is served in-room or on the back porch.
Guests and staff must wear masks and socially distance.
The fitness center is closed.
Proper social distancing must be maintained at the seasonal pool.

33 Main

Book 33 Main starting at $289 per night

33 Main epitomizes casual chic. Berkshire-bred designer Annie Selke recently renovated this Federal-style building in the heart of downtown Lenox, furnishing the eight individually-appointed rooms with top-quality furniture and accessories that are for sale in her showroom across the street.

Selke favors a calm color palette with touches of Robin’s egg blue and soft pastels. Accents like grasscloth wallpaper, patterned window treatments, chunky knit throws, sheepskin decorative pillows, and hooked rugs add panache. Rooms all have a handmade Hastens mattress, which is the same company that supplies the Swedish Royal Court, so you’ll literally be sleeping like a king. Bathrooms have soaking tubs and an array of certified organic lotions and soaps from Farmaesthetics.

You’ll be pampered from the moment you arrive with in-room treats like fresh flowers and just-baked cookies. A scrumptious breakfast and late afternoon nibbles in the parlor are included in the room rate.

Trip Advisor Ranking: 6 out of 19 B&Bs in Lenox

Booking.com Rating: 9.4 out of 10

Pros: With the look and feel of a gracious estate, the inn presents a design-forward aesthetic.

Cons: If you’re looking for an anonymous experience, the inn may be a tad too intimate.

COVID-19 cleaning and safety procedures:

Guests are required to have a negative COVID test result within 72 hours of arrival.
Guests and staff are required to wear masks in public areas.
Hand sanitizer is available throughout the inn.
Breakfast and cocktail time are staggered to reduce person-to-person contact.
All guest rooms and common areas are cleaned using bacteria-killing ingredients in accordance with CDC guidelines.
No in-room housekeeping once the guest has arrived.
Rooms are kept vacant for 24 hours between guests and sanitized with a UV light.

Wheatleigh

Book Wheatleigh starting at $853 per night

For a refined luxury experience worthy of a splurge, it’s hard to beat Wheatleigh. This romantic, 19-room hotel is located on what was originally a private country estate and features magnificent grounds. For guests who can afford the steep price tag, a night at this Italianate-style mansion is an elegant immersion in aristocratic living.

It’s an oasis of rambling wooded paths and lush flower beds. Towering porticos, fountains, and fresh floral arrangements add to the hotel’s dignified feel.

Guest rooms offer great attention to detail from the fine antique furniture, marble-topped tables, and soaring ceilings to the museum-quality artwork throughout. Bathrooms feature large soaking tubs and separate showers. Modern amenities include Roku-enabled televisions and Bose sound systems.

The on-site restaurant, Portico, has won numerous awards for its gourmet cuisine, noteworthy wine cellar, and fine service.

Trip Advisor Ranking: 9 out of 18 hotels in Lenox (But don’t let that fool you. Most guests of this Forbes Five-Star hotel gave the property a perfect score in all categories with the exception of value, due to its soaring nightly rate.)

Pros: You’ll feel like a time machine has whisked you back to the Gilded Age. A fabulous breakfast is included in the rate.

Cons: Prices are prohibitive for many.

COVID-19 cleaning procedures: The hotel feels like a private sanctuary so social distancing is inherent in the layout. Additional safety measures include:

Temperature checks for guests on arrival and staff at the start of each shift.
The grounds and restaurant are operating at 40% capacity, exclusively for hotel guests.
Numerous guest rooms are purposefully left vacant.
Guests must have received a negative COVID test result within 72 of arrival.
Hand sanitizer in guest accommodations and public areas.
Staff wears masks at all times, as do guests when in public spaces.
Housekeeping and valet services are customizable according to guest preference.

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