Photo by Chris Addams

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Compare 4 Chalets in Housatonic with updated reviews, rates, and availability.

Little Longbow Lakefront Chalet
Aerial view

Little Longbow Lakefront Chalet

10.0 out of 10, Exceptional, (9)
"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "
Little Longbow Lakefront Chalet
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Main level open space (old setup)

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.

9.8 out of 10, Exceptional, (21)
"Beautiful well kept house in the Berkshires, great view and layout. Close to amazing nature and Great Barrington if you need anything. Wonderful trip!"
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
garden view of the back of the cabin, with the deck

Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!

8.8 out of 10, Excellent, (3)
"We really enjoyed our stay at this adorable A frame home. The home was a quick drive to tanglewood and the views were beautiful. The owner was very communicative and prompt with answering any questions. "
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
SRC-Hudson Valley/Berkshires Cultural Corridor
Property grounds

SRC-Hudson Valley/Berkshires Cultural Corridor

SRC-Hudson Valley/Berkshires Cultural Corridor
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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Other property types in Housatonic

Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 547
AED 600 total
includes taxes & fees
26 Nov - 27 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

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

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.