Our top choices for The Berkshires hotels

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

Lenox

Mark

￥19,925 total

includes taxes & fees

Jun 11 - Jun 12

Berkshires Untold

Lenox

Thomas

￥25,404 total

includes taxes & fees

Jun 16 - Jun 17

Berkshire Mountain Lodge

Pittsfield

Sade

￥29,224 total

includes taxes & fees

Jun 14 - Jun 15

Quality Inn Great Barrington

Great Barrington

Braynd

￥16,852 total

includes taxes & fees

Jun 14 - Jun 15

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

andrew

￥25,704 total

includes taxes & fees

Jun 16 - Jun 17

Hotel On North

Pittsfield

KEITH AND SHIRLEY

￥32,073 total

includes taxes & fees

Jun 14 - Jun 15

The Red Lion Inn

Stockbridge

molly

￥35,124 total

includes taxes & fees

Jun 22 - Jun 23

The Cornell Inn, Lenox & The Berkshires

Lenox

Arthur

￥29,827 total

includes taxes & fees

Jun 22 - Jun 23

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

Pittsfield

Kathleen

￥24,189 total

includes taxes & fees

Jun 14 - Jun 15

The Whitlock

Lenox

Linda

￥27,769 total

includes taxes & fees

Jun 15 - Jun 16

Hideaway Inn Lenox

Lenox

Leonardo

￥20,116 total

includes taxes & fees

Jun 11 - Jun 12

Vacation Village in the Berkshires

Williamstown

Melissa

￥24,859 total

includes taxes & fees

Jun 14 - Jun 15

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Anandaraja

￥20,642 total

includes taxes & fees

Jun 14 - Jun 15

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

Kimberly

￥27,164 total

includes taxes & fees

Jun 14 - Jun 15

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Great Barrington

Yekaterina

￥13,767 total

includes taxes & fees

Jun 17 - Jun 18

The Little Lion

Great Barrington

Mia

￥15,768 total

includes taxes & fees

Jun 14 - Jun 15

Quality Inn Lee - Lenox South

Lee

Cheri

￥21,958 total

includes taxes & fees

Jun 14 - Jun 15

The Villager Motel

Williamstown

Monica

￥15,921 total

includes taxes & fees

Jun 14 - Jun 15

Shaker Mill Inn

West Stockbridge

Mervin

￥27,846 total

includes taxes & fees

Jun 17 - Jun 18

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

robert

￥14,154 total

includes taxes & fees

Jun 11 - Jun 12

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Vacation Rentals in The Berkshires

Condo

Vacation Village in the Berkshires

Williamstown

"So clean and spacious, had everything you need for a nice getaway"

Apartment

Vacation Rental Home in the Berkshires!

Williamstown

"This little guest house is a gem. Charming, comfortable and with a location that can’t be beat as a base for touring the northern Berkshires and southern Vermont. Everything was in good order, check-in was easy, and the place is well equipped with kitchen essentials. The views are gorgeous. "

Cottage

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Sandisfield

"We had an amazing experience! Such a beautiful home and amazing host! We loved it! Definitely staying here again. Highly recommend! Thank you! "

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Stay near popular The Berkshires attractions

Tanglewood Music Center

4.8/5 (457 reviews)

Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.

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Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Everything was good but restaurant need to close later. Parking was an issue."

Berkshires Untold

10/10 Excellent

"The hotel was beautiful. My room was very nice exactly what I needed. The decor was very inviting and the bathroom was amazingly beautiful as well as the lounge and grounds of the property. My only one wish was that there was coffee in the room. Although you just had to walk to the lobby to get coffee in the morning, you had to get up and get dressed first which would have been more convenient if coffee was already in the room."

The Red Lion Inn

8/10 Good

"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."

The Whitlock

10/10 Excellent

"The location of this hotel is excellent, right in the town center of Lenox, close to all the shops and restaurants. I was a little concerned initially about the reviews I read regarding the level of cleanliness of the rooms which I am extremely particular about. The room was very clean so maybe the issue has been addressed. Communication with staff via text which normally would be concerning was also very prompt and quick. They respond to texts right away and always very kind so shouldnt be a concern for those who are concerned that they are not speaking to someone in person directly. Will definitely stay again if the rates are reasonable."

Vacation Village in the Berkshires

10/10 Excellent

"This is a big beautful modern condo complex about 20 mins outside Wiilamstown (to the north) or Pittsfield (to the south). Huge swimming pools - one indoors, one out. Beautiful views of the Berkshires. Quiet rural environment. I could hear the frogs singing and the cricketa chirp at night. Excellent value for the money. Friendly staff. I got a one-bdrm condo for the price of a standard hotel. No grocery atores nearby some come with supplies if you plan to cook."