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Compare 465 Vacation Homes in Western Massachusetts 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
10 May - 11 May

Author Stephen Oates Once Owned
Author Stephen Oates Once Owned
8.0 out of 10, Very Good, (2)
The price is AED 1,466
AED 2,261 total
includes taxes & fees
12 May - 13 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

PICON COZY
PICON COZY
7.6 out of 10, Good, (65)
The price is AED 275
AED 625 total
includes taxes & fees
15 May - 16 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)

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
9.8 out of 10, Exceptional, (98)

1810 Brook Side Mill/House / EV Level 2 Charging on Site
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (73)

Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
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 Western Massachusetts

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1804)
The price is AED 403
AED 490 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
10 May - 11 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 Western Massachusetts hotels
Recent reviews of Western Massachusetts hotels

Holiday Inn Express Springfield Downtown by IHG
5/5 Excellent
"The room was clean and nicely updated. "
A verified traveler stayed at Holiday Inn Express Springfield Downtown by IHG
Posted 18 hours ago
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