98 Properties in The Berkshires, Massachusetts, United States of America. November 19, 2025 through November 20, 2025

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Tanglewood Music Center

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Massachusetts Museum of Contemporary Art

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98 properties

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A neatly arranged bedroom with a large bed, a chair, and a window with a view of trees.

Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

33 Main

Property class 4 out of 5

Lenox

Breakfast included

Jul 25 - Jul 26

1010 out of 10

Exceptionalexceptional

74 reviews(74 reviews)

We are sold out

33 Main is sold out for your dates on our site.

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A compact living space with a kitchenette, a dining area, and a sofa.

A building with a 'REGISTRATION' sign above the entrance, a white picket fence, and flower baskets on the porch.

The Central Downtown Inn & Suites

Property class 4 out of 5

Pittsfield

8.68.6 out of 10

Excellentexcellent

379 reviews(379 reviews)

$199 nightly

The current price is $222 total

$222 total

Total with taxes and fees

We have 2 left at this price

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A white building with large windows and a sign that reads "The Wick".

A mountainous landscape with autumn foliage and a river.

The Wick, Hudson, A Tribute Portfolio Hotel

Property class 4 out of 5

Fully refundable

Reserve now, pay later

8.88.8 out of 10

Excellentexcellent

571 reviews(571 reviews)

$699 nightly

The current price is $790 total

$790 total

Total with taxes and fees

We have 1 left at this price

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Photo gallery for 33 Main

33 Main

Photo gallery for The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

Photo gallery for The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel