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Our top choices for Western Massachusetts cottages
Beautiful 2-bedroom cottage on Robert Frost Trail
Beautiful 2-bedroom cottage on Robert Frost TrailAmherst
The price is HK$1,368
HK$2,240 total
includes taxes & fees
4 Jan - 5 Jan 2026
Trainmaster's Inn - Caboose
Trainmaster's Inn - CaboosePalmer
9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
Edward L.
The price is HK$1,166
HK$2,639 total
includes taxes & fees
1 Jan - 2 Jan 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville LakeStafford
9.6 out of 10, Exceptional, (30)
"Great host- fun property!"
Mary F.
The price is HK$595
HK$1,987 total
includes taxes & fees
6 Jan - 7 Jan 2026
Wilmington Retreat Near Trails, Skiing & Festivals
Wilmington Retreat Near Trails, Skiing & FestivalsWilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
Anonymous traveller
The price is HK$1,399
HK$2,745 total
includes taxes & fees
20 Jan - 21 Jan 2026
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. MonadnockRindge
10.0 out of 10, Exceptional, (22)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
Nicole B.
The price is HK$1,364
HK$2,854 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Cozy Upstate Lakefront 2BR Retreat with Kayaks & FireplaceNassau
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
Terry O.
The price is HK$1,224
HK$2,842 total
includes taxes & fees
4 Jan - 5 Jan 2026
The price is HK$7,694
HK$14,296 total
includes taxes & fees
26 Jan - 27 Jan 2026
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 Western Massachusetts Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
Find out more about Western Massachusetts
Western Massachusetts Cottages information
Number of reviews | 63 |
|---|---|
Accommodation | 110 Cottages |
Lowest Price | HK$1,987 |
Highest Price | HK$14,296 |
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