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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Western Massachusetts and around

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 €361
includes taxes & fees
19 Aug - 20 Aug
The Blue Elm - A Historic Berkshire Cottage
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, (15)
"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 €307
includes taxes & fees
1 Sept - 2 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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 €287
includes taxes & fees
19 Aug - 20 Aug
Trainmaster's Inn - Caboose
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is €1,484
includes taxes & fees
15 Sept - 16 Sept
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

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"Walking distance to MassMOCA and several good restaurants and coffee shops. "
James 2-night trip
Posted 2 days ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between €361 and €361 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 organise 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!