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Cottages in Western Massachusetts

Our top choices for Western Massachusetts cottages

The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "
The price is ￥29,388
￥60,566 total
includes taxes & fees
Aug 25 - Aug 26
The Blue Elm - A Historic Berkshire Cottage
Trainmaster's Inn - Caboose
Private kitchen

Trainmaster's Inn - Caboose

9.6 out of 10, Exceptional, (8)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
The price is ￥22,041
￥48,149 total
includes taxes & fees
Aug 25 - Aug 26
Trainmaster's Inn - Caboose
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

9.6 out of 10, Exceptional, (18)
"This lake house is a perfect, quiet & very pretty getaway! We absolutely loved our stay! The host was so sweet and easy to contact. We will be back!"
The price is ￥22,041
￥51,613 total
includes taxes & fees
Sep 1 - Sep 2
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is ￥152,230
￥261,553 total
includes taxes & fees
Sep 21 - Sep 22
Berkshires farm, 30+ guests, 50 acres
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great option a little further away from Lenox! Clean and great service. "
Reetika 2-night trip
Posted 14 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between ￥29,388 and ￥29,388 per night. These stays offer a chance to reconnect with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Western Massachusetts?
Western Massachusetts has 122 cottages to choose from. Enter your dates and destination and organize your ideal getaway today.
Why book your cottage in Western Massachusetts with Expedia?
Reserving a cottage in Western Massachusetts is as easy as entering your travel dates and picking your ideal place for a getaway in nature. From luxurious retreats to low-cost stays and cottages that come with perks like a hot tub, Expedia has something for all styles. As for irresistible deals? We've got you covered!