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Featured Chalets in The Berkshires

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
3 bedrooms, desk, iron/ironing board, travel cot

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.
Little Longbow Lakefront Chalet
Smart TV, fireplace

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

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!
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 The Berkshires

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1751)
"Nice and quiet family get a way"
The price is AU$348
includes taxes & fees
5 Jan - 6 Jan
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (922)
"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...
The price is AU$334
includes taxes & fees
5 Jan - 6 Jan
Jiminy Peak Mountain Resort
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
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.