Check out these popular cities in The Berkshires

Lenox

Festivals & Music, Theater & Performing Arts, Wellness Retreat

25 hotels

One of 260 reviews:

"A beautiful western Massachusetts town, very walkable, with nice boutiques and galleries. We visited in October, so some restaurants had closed for the season. We, however, were fortunate to have an incredible meal at Firefly Gastropub. It was popping the night we were there! We had seats at the bar and were attended by the amazing bartender who must have been wearing roller skates! I highly recommend a visit to the area."

Guest review bySusan

United States

Pittsfield

Theater & Performing Arts, Historical Landmarks, Museums & Galleries

16 hotels

One of 108 reviews:

"Tanglewood is close to Pittsfield- great location. We love staying in Pittsfield. There are many terrific activities to do in the Berkshires- museums, theaters, dance, Shakespeare, hiking, etc. Lots of wonderful scenery in the Berkshires!.Many really good restaurants and shops, too."

Guest review byJudith

United States

Great Barrington

Hiking, Theater & Performing Arts, Ski & Winter Sports

20 hotels

One of 89 reviews:

"Terri and Terry were outstanding hosts. They were both easy to talk to and really went out of their way to make your stay very special. The breakfast was outstanding and Terri's recommendations were restaurants was on the mark. Lovely the music room and the juke box . Fantastic selection of Vinyl Albums on a great stereo.The inside of the B and B was very comfortable and cozy. Already recommended the place to three friends."

Guest review byAppelman

United States

South Lee

Countryside, Rolling Hills, Hiking

2 hotels

Lee

Shopping, Hiking, Countryside

19 hotels

One of 105 reviews:

"Lee is a small town near Stockbridge and Lenox. It’s in the Berkshire Mts. The Fall foliage is worth the trip. Colors were popping! We visited: Olivia’s Outlook (a stunning view of the valley and mountains), the Norman Rockwell Museum (well worth a visit here for $23/senior) the Kripalu Yoga Campus (beautiful views of the surrounding mountains), Pleasant Valley Nature Sanctuary (trails and information of the land). In town we walked to dinner and breakfast. Morgan House Inn is a historical fixture serving food from 4-8 pm. We had the best Angus burgers and fresh-cut fries ever! Park 51 had comfortable outdoor seating and the food was excellent and delicious. My breakfast at Rosie’s was superb: a fresh croissant with fluffy, scrambled eggs, applewood bacon and creamy cheese. The accompanying fresh greens with a creamy dressing were delicious."

Guest review byNancy B

United States

North Adams

Museums & Galleries, Industrial Heritage, Hiking

4 hotels

One of 16 reviews:

"A very "walkable" town that has much to offer - a good selection of restaurants and arts activities. The presence of MCLA and the many state and local parks really enhances the area's cultural and outdoor offerings. Although there a a handful of stately homes that are need of repair, this only enhances the charm of the city. Within an hour's walk, I was able to take in a good portion of the city. Highly recommend Ramunto's Brick Oven Pizza - delicious food and an easy walk from Downstreet Hotel and other points downtown."

Guest review byCathleen Stephen

United States

Williamstown

Museums & Galleries, Academic culture, Theater & Performing Arts

20 hotels

One of 184 reviews:

"Nice little town. Friendly businesses and residents. Owner recommended Waterstreet Grill after we told her what type of food we were looking for when we arrived. She showed us how to get there. The restaurant staff were friendly and food was great there too."

Guest review byRebecca

United States

Stay in The Berkshires's best hotels!

The Williams Inn

Hotel in Williamstown

The Williams Inn has a fitness center, shared lounge, a restaurant and bar in Williamstown.

M

MWS

From

United Kingdom

Its location close to Williams’ campus was great. The Barn restaurant is also great

Scored out of 10, guest rating 9.4

Wonderful - What previous guests thought, 165 reviews

Price from

$329

1 night, 2 adults

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Courtyard by Marriott Lenox Berkshires

Hotel in Lenox

Located in Lenox, 2.9 miles from Cranwell Spa & Golf Club, Courtyard by Marriott Lenox Berkshires provides accommodations with free bikes, free private parking, a fitness center and a terrace.

W

William

From

United States

My wife and I were the first to visit the Lenox Marriott when it opened. It has never disappointed.

Scored out of 10, guest rating 9.0

Wonderful - What previous guests thought, 107 reviews

Price from

$203.15

1 night, 2 adults

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Hotel on North

Hotel in Pittsfield

Located in Pittsfield and within 8.2 miles of Cranwell Spa & Golf Club, Hotel on North has a bar, non-smoking rooms, and free WiFi throughout the property.

l

lynn

From

United States

Beautiful hotel, nicely appointed, comfortable bed, friendly staff

Scored out of 10, guest rating 9.2

Wonderful - What previous guests thought, 190 reviews

Price from

$179

1 night, 2 adults

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Prospect Berkshires

Hotel in North Egremont

Located in North Egremont, 11 miles from Norman Rockwell Museum, Prospect Berkshires provides accommodations with free bikes, free private parking, an outdoor swimming pool and a garden.

C

Chaitanya13

From

United States

Fantastic property for peace, solitude, good food, sauna, exploring local charming towns/villages. I'll revisit in different seasons.

Scored out of 10, guest rating 9.5

Exceptional - What previous guests thought, 24 reviews

Price from

$425

1 night, 2 adults

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Doctor Sax House

Hotel in Lenox

Located in Lenox, 1.5 miles from Tanglewood Musical Center, Doctor Sax House has accommodations with a shared lounge, free private parking, a terrace and a restaurant.

R

Robert

From

United States

Lenox is one of the most inviting towns in the Berkshires and the beautifully restored Dr Sax House is a gem in its center. We arrived on the coldest day of winter to celebrate our wedding anniversary, but Brian and Kelly and their solicitous staff gave us the warmest welcome and most delightful stay we have had anywhere. I don't think we've ever encountered a bedroom and bathroom with so many thoughtful amenities: not just toiletries but everything you might have forgotten, not just a yoga mat but a gym bag filled with small weights and accessories. Their cozy restaurant Dulu is en suite with a beautifully appointed bar. The menu is imaginative and my baked halibut was the most delicious I have enjoyed - ever. With temperatures in the single digits it was a plus for us to be able to simply hang out at the Inn, but under balmier conditions all the artistic and culinary attractions that Lenox has to offer are right outside the door. It's also a perfect base for Tanglewood and many other local cultural activities. We look forward to our return soon!

Scored out of 10, guest rating 9.1

Wonderful - What previous guests thought, 26 reviews

Price from

$632.50

1 night, 2 adults

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Tourists

Hotel in North Adams

Located in North Adams, 17 miles from Bennington Battle Monument, Tourists has accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a shared lounge.

v

valentina

From

United States

Absolutely outstanding. 10/10. The airport rooms- some of the best food I’ve ever had. Cannot wait to return

Scored out of 10, guest rating 9.4

Wonderful - What previous guests thought, 26 reviews

Price from

$299

1 night, 2 adults

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Hampton Terrace Inn

Hotel in Lenox

Hampton Terrace Inn has a garden, terrace, a bar and tennis court in Lenox.

A

Antonio Andrei

From

Romania

The houses have charm. The fireplace is amazing. The location is close to a lot of touristic spots (5-15 min driving).

Scored out of 10, guest rating 9.3

Wonderful - What previous guests thought, 30 reviews

Price from

$260.70

1 night, 2 adults

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Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hotel in Pittsfield

Your Gateway to Relaxation and Adventure in the Heart of the Berkshires Discover the perfect home base for your next getaway at our brand-new hotel, nestled in the scenic Berkshires of Western...

J

Jaqueline

From

United States

Cleanliness. Closet and place to put luggage. Didn't need to use the floor. New bathroom. All was great

Scored out of 10, guest rating 9.2

Wonderful - What previous guests thought, 78 reviews

Price from

$130

1 night, 2 adults

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Berkshires Untold

Hotel in Lenox

Located in Lenox, 3.4 miles from Cranwell Spa & Golf Club, Berkshires Untold has accommodations with a shared lounge, free private parking, a terrace and a restaurant.

S

Sara

From

Canada

the aesthetic, so detail oriented and has a very nice and cozy vibe as well as the farm to table ethos.

Scored out of 10, guest rating 8.3

Very Good - What previous guests thought, 528 reviews

Price from

$152.10

1 night, 2 adults

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Hilton Garden Inn Lenox Pittsfield

Hotel in Pittsfield

Hilton Garden Inn Lenox/Pittsfield/Berkshires offers accommodations in Pittsfield. The hotel has a fitness center and indoor pool, and guests can enjoy a meal at the restaurant or a drink at the bar.

S

Seber

From

United States

Can't beat a Hilton Garden Inn. Always worth paying a little extra. Excellent restaurant Jae's for Asian cuisine without leaving the premises!

Scored out of 10, guest rating 8.3

Very Good - What previous guests thought, 112 reviews

Price from

$177.66

1 night, 2 adults

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