15 Hotels in the Berkshires: Best Hotels, Inns, Motels, and Resorts

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If you’re looking for a classic New England experience, then you can’t go wrong with a visit to the Berkshires.

This collection of small towns in Western Massachusetts is known for its scenic beauty and abundance of cultural attractions. 

Whether you’re a history buff or an outdoor enthusiast, there is plenty to do- from the Hancock Shaker Village and Berkshires Museum in Pittsfield to the Mohawk Trail State Forest in Charlemont.

And if you’re looking to extend your stay to enjoy more of this place’s locality and attractions, then check out our list of hotels in the Berkshires as the base of all your adventures.

You’ll find accommodations from highly rated hotels and charming inns to luxurious resorts that’ll definitely make your stay worthwhile.

For more ideas on accommodations in Massachusetts, you can also look at our guides to hotels in Provincetown, hotels in Plymouth, and places to stay in Salem, MA.

Best Hotels in the Berkshires

The following highly-rated hotels have excellent amenities and are situated close to popular sites, shops, and restaurants in the Berkshires.

If you’re visiting during the off-season, check out the fun activities during winter in the Berkshires.

The Red Lion Inn Berkshires

One of the best hotels in the Berkshires is the Red Lion Inn (30 Main Street, Stockbridge), which has two on-site restaurants that serve breakfast, lunch, dinner, and a cocktail hour. 

There is also an outdoor pool and hot tub that are open year-round and a gift shop at the hotel. 

The property has convenient access to the Norman Rockwell Museum (9 Glendale Rd), antique shops, a golf course, and Tanglewood (297 West St). 

All the rooms sleep at least two people, and there are many options ranging from standard hotel rooms to the largest two-bedroom village suite, which has two twin beds, a sofa bed, and a queen bed. 

Holiday Inn & Suites Pittsfield-Berkshires

Holiday Inn Berkshires (1 West Street, Pittsfield) is within driving distance of Lake Onota, mountains, and golf courses. 

The hotel has a lot of great amenities, including an indoor pool, hot tub, day spa, and a restaurant open for breakfast and dinner. 

Rooms in the property range between 300 and 600 sq ft in size and fit anywhere from two to six adults.

Guests can also explore the iconic Hancock Shaker Village (1843 W Housatonic St), which is just less than a 15-minute drive from the hotel.

Tourists

Tourists (915 State Road, North Adams) is a great option if you are looking at boutique hotels in the Berkshires. 

The hotel has everything you need, including an outdoor swimming pool, a restaurant, a bar and lounge, and a sun terrace. 

All the rooms have a king bed with either a poor garden view or a balcony, ranging in size from 315 to 370 sq ft.

There is also a 600 sq ft garden suite with a king bed and three twin beds and a 670 sq ft king suite with a balcony.  

Inns in the Berkshires

The Berkshires have plenty of inns and bed-and-breakfasts to choose from. 

Whether you’re looking for a rustic country setting or a posh downtown location, there’s sure to be an inn that fits your needs. 

The Inn at Stockbridge

The Inn at Stockbridge (30 East Street, Stockbridge) is one of the luxury inns in the Berkshires.

Located just ten minutes from Tanglewood, this property is near a golf course, Norman Rockwell Museum (9 Glendale Rd), and Berkshire Theatre Festival (6 East St). 

At the inn, there is an outdoor pool; guests get a full breakfast, plus snacks available during the day and wine and cheese in the evening. 

There are many room options to choose from for a two-person stay, including standard king rooms, superior king rooms, and a queen room with a garden view.

The place also has king rooms available that can accommodate three to four people and features either a pool view or a spa bath.

Wainwright Inn

Wainwright Inn (518 Main Street, Great Barrington) offers amenities such as free parking, free Wi-Fi, a terrace, and a daily breakfast. 

Every room at the inn comes with a kitchenette, a dining area, and a cable TV, and nearby are areas for skiing and hiking.

The rooms sleep two to four people, and the standard rooms range in size from 250 sq ft to 396 sq ft with two full beds, a queen bed, or a king. 

There is also a 400 sq ft family suite with a king bed in one room and two twin beds in the other. 

Whistler’s Inn

Whistler’s Inn (5 Greenwood Street, Lenox) is close to the Tanglewood Musical Center, the Shakespeare & Company Theater (70 Kemble St), and just five minutes on foot from Kennedy Park, where you can hike and bike.

At the inn, guests get a full breakfast, tea, and cookies in the afternoon and access to a parlor with a piano and a library. 

The rooms are of average size ranging from 64 sq ft deluxe queen rooms to a 350 sq ft family suite.

Their queen rooms can accommodate up to two persons, but if you’re staying as a group or family, you may opt for their family suite, which can sleep up to 4 people.

Motels in the Berkshires

Here’s a look at some of the best motels in the Berkshires, with most of them located close to the downtown area.

Williamstown Motel

Williamstown Motel (295 Main Street Route 2, Williamstown) is a mile and a half from downtown Williamstown, and even closer to the motel are the Clark Art Institute (225 South St), restaurants, and bars. 

The rooms have a fridge, microwave, coffee maker, and a TV.

They have three room options, including a 192 sq ft queen room with one queen bed, a 300 sq ft queen room with two queen beds, and a 300 sq ft room with three double beds.

The rooms at this motel are pretty spacious and can comfortably sleep at least three people.

Berkshire Inn

Berkshire Inn (150 West Housatonic Street, Pittsfield) is a great motel in the Berkshires with an outdoor pool, free breakfast in the summer, and a picnic area. 

The rooms in the inn are around 250 sq ft with a king bed or two queens, or 300 sq ft with two queen beds and a sofa bed- all rooms come with a cable TV, a fridge, and a microwave. 

You can get from the motel to downtown Pittsfield, the Canoe Meadows Wildlife Sanctuary, a ski area, and a mountain resort in 15 minutes or less. 

The Berkshire Museum (39 South St) is also just a 3-minute drive from the property.

Monument Mountain Motel

Monument Mountain Motel (247 Stockbridge Road, Great Barrington) is in a great location near the Butternut Ski Resort (380 State Rd) and to plenty of shops and restaurants. 

The hotel has a patio, a picnic area, and a BBQ area. 

You have the choice between a room with a king bed, a queen bed, or two queens. 

Maple Terrace Motel

Maple Terrace Motel (555 Main Street, Williamstown) has beautiful mountain views, a heated outdoor pool, and free Wi-Fi.

You are within driving distance from a golf course, ski areas, and a mile or less to the Clark Art Institute and plenty of restaurants and bars. 

You can choose between a 212 sq ft room with one queen bed or a 268 sq ft room with two double beds. 

Scenic mountain views with trees and farmlands in Williamstown, MA

Resorts in the Berkshires

The following are lists of resorts in the Berkshires if you’re looking for accommodation that offers entertainment and recreational activities like hiking, swimming, or skiing.

Vacation Village in the Berkshires

Vacation Village (276 Brodie Mountain Road, Hancock) is a great option if you are looking for luxury resorts in the Berkshires.

The resort is surrounded by beautiful mountains where you can bike, ski, fish, and swim or enjoy the local restaurants and historical sites. 

And the rooms have balconies or patios, plus a full or partial kitchen. 

Even the smallest one-bedroom rooms, with either a king, queen, or full bed plus a sofa bed, are relatively large at 700 to 850 sq ft. 

The two-bedroom rooms sleep eight people comfortably at 1400 sq ft. 

Jiminy Peak Mountain Resort

Another one of the best resorts in the Berkshires, MA, is the Jiminy Peak Mountain Resort (37 Corey Road, Hancock).

The resort has everything you need no matter what time of year you visit, including two restaurants, ski slopes, rentals, lessons, an outdoor pool, an indoor hot tub, and tennis courts. 

And all the power at the resort is supplied by 100% renewable energy. 

You can opt for a standard 500 sq ft suite with a king bed, kitchenette, and a living room with a sofa bed. 

Or, for large groups, there are 900 sq ft two bedroom and 1500 sq ft three bedroom apartments with full kitchens, large living spaces with a fireplace, multiple bathrooms, and enough beds to sleep six to eight people. 

The Ponds at Foxhollow by Capital Vacations

The Ponds (3 Foxhollow Drive, Lenox) is another resort with an outdoor pool, an indoor pool, a hot tub, and a sauna. 

The resort has free bikes for guests to use, plus areas for fishing and canoeing nearby. 

The rooms are apartment style, and you can choose from a 600 sq ft one bedroom that sleeps four or an 800 sq ft two bedroom that sleeps six. 

Spa Resorts in the Berkshires

If you’re looking for a relaxing and rejuvenating getaway, consider spending some time at one of Berkshire County’s amazing spa resorts. 

From beautiful surroundings to top-notch treatments, these spa resorts are the perfect place to rest after a long day of exploring.

Chambery Inn

One of the best resorts in the Berkshires with a spa is the Chambery Inn (199 Main St., Lee) which used to be a schoolhouse.

At the inn, you get breakfast delivered to your room, and they offer spa packages that include in-room massages, either solo or for couples, and some of the rooms come with a spa tub.

There are standard rooms that are 150 to 165 sq ft and have a full, queen, or king bed, or there are 500 sq ft suites with a king bed or two queens.

Wheatleigh

Wheatleigh in the Berkshires (11 Hawthorne Road, Lenox) sits on 22 acres, including an outdoor pool, a tennis court, a massage room, and three American restaurants. 

Near the resort is a golf course, Tanglewood, and the Berkshire Botanical Gardens.

Most rooms have one king bed, but there are also options for a queen or a full room ranging in size from 159 sq ft for the standard rooms to 573 sq ft for the largest suites with a balcony or patio and a sofa. 

Eastover Estate and Eco Village

Finally, the Eastover Estate and Eco Village (430 East Street, Box 2282, Lenox) is perfect for relaxation.

There are 600 acres at this resort, and they offer yoga classes, guided hikes, wellness classes, and a beautiful garden on the property.

Located nearby the resort is a ski area, a golf course, and the Tanglewood Musical Center. 

The spa resort has 252 to 336 sq ft double, queen, and king out-of-mansion rooms, which can sleep up to three people and features a mountain view and complimentary room service for a 3-night stay or longer.

If you’re looking for spacious rooms that can accommodate a family or a group, they also have suite rooms that go as big as 398 sq ft which is good for up to six people and comes with comfy beds and luxurious private bathrooms.

For something less extravagant, you can get a twin bed in a 252 sq ft shared dorm with an ensuite bathroom designated by gender, or you can get a king, queen, or full bed private room.

Final Thoughts

If you’re looking for a nice place to rest your head during your next visit, be sure to check out one of these hotels in the Berkshires.

Did you stay at any of the hotels we mentioned? Please feel free to share your experience in the comments below.

And if you want to explore more places in Massachusetts, we have guides that can help you on your next trip:

 

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