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Compare 338 Vacation Homes in The Berkshires with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (245)
The price is AED 551
AED 841 total
includes taxes & fees
9 May - 10 May

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,016
AED 3,810 total
includes taxes & fees
12 May - 13 May

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (151)

Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (214)

Lakeside Oasis Just You, The Lake & The View!
Lakeside Oasis Just You, The Lake & The View!
9.8 out of 10, Exceptional, (70)

Heart of Lenox Walk to Town Cozy Cottage!
Heart of Lenox Walk to Town Cozy Cottage!
10.0 out of 10, Exceptional, (71)

The Race Mountain House
The Race Mountain House
10.0 out of 10, Exceptional, (1)
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
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1804)
The price is AED 372
AED 455 total
includes taxes & fees
11 May - 12 May

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (929)
The price is AED 488
AED 545 total
includes taxes & fees
9 May - 10 May

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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.
Recent reviews of The Berkshires hotels
Recent reviews of The Berkshires hotels

The Williams Inn
5/5 Excellent
"A delightful property in every way. We had comfy beds, lots of quiet (our rooms were adjacent to the elevator and we never heard a peep), loved the complimentary coffee, tea, and water. Enjoyed the public spaces and the restaurant. Easy parking, steps from Spring Street. I could go on and on, but the summary is I’d be so pleased to stay here again. "
A verified traveler stayed at The Williams Inn
Posted 18 hours ago
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