A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

Resorts in Berkshire County

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Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 Dec

Top Cities in Berkshire County

A historic building with classical architecture, a traffic light, and a yellow taxi.
ResortsResorts

Pittsfield

Pittsfield
A river surrounded by autumn-colored trees and a forested hill.
ResortsResorts

Stockbridge

Stockbridge

Our top choices for Berkshire County resorts

A spacious kitchen with a large wooden table, built-in cabinets, and a view of the outdoors through large windows.

1. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice area that was reasonably close to MasMOCA."
United States
Jeff F.
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
A rustic interior with a stone fireplace, wooden ceiling beams, a bar area, and a hanging antler chandelier.

2. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Easy booking, great ski weekend. Very positive experience!"
United States
Faith V.
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
A rustic interior with a stone fireplace, wooden ceiling beams, a bar area, and a hanging antler chandelier.

3. Hot SKI-in SKI-out Rentals Bentley Brook Resort!

Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Hancock
10.0 out of 10, Exceptional, (1 review)
"Great property! Great location. Smooth check-in."
United States
erica l.
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
A living room with a sofa, armchair, coffee table, TV, and a ceiling fan.

4. July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires

July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires
Lee
July 12-19 2026: Resort with 2 bedrooms and AC in the delightful Berkshires
A multi-story hotel with balconies, a pond with rocks and lily pads, and a clear sky.

5. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA

Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Lee
Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
A multi-story hotel with balconies, a pond with rocks and lily pads, and a clear sky.

6. Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA

Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
Lee
Welcome to Holiday Inn Club Vacations Oak 'n Spruce Resort, South Lee, MA
A building with arched windows and a well-maintained hedge in front.

7. Canyon Ranch Lenox

Canyon Ranch Lenox
3.0 star property
Lenox
Canyon Ranch Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Berkshire County Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Beautiful property, spacious room. Easy parking"
Diana 1-night trip
Posted 2 hours ago
Hotel On North

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