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Dec 19 - Dec 21
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Mar 27 - Mar 29

Cottages in Western Massachusetts

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

Cottage in Stafford

9.8 out of 10, Exceptional, (29)
"FANTASTIC STAY! there was an issue after arrival that was QUICKLY addressed... rest of stay was amazing! Beautiful home. Great kayaks.. lots of fishing!QUICK AND PLEASANT COMMUNICATIONS.THANK YOU!!!"
United States
Michelle O.
$273 nightly
The price is $309
Dec 9 - Dec 10
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Private kitchen
Trainmaster's Inn - Caboose

Cottage in Palmer

9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
$310 nightly
The price is $328
Dec 7 - Dec 8
Total with taxes and fees
Trainmaster's Inn - Caboose
Exterior
Tiny house on the Ashuelot river family and pet friendly

Cottage in Swanzey

Tiny house on the Ashuelot river family and pet friendly
Exterior
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

2.0 star property
$326 nightly
The price is $331
Dec 10 - Dec 11
Total with taxes and fees
Pet-Friendly Hudson Escape w/ Hot Tub
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Cottage in Rindge

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."
United States
Nicole B.
$331 nightly
The price is $359
Dec 7 - Dec 8
Total with taxes and fees
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior
Berkshires farm, 30+ guests, 50 acres

Cottage in New Lebanon

2.0 star property
$1,744 nightly
The price is $1,765
Dec 7 - Dec 8
Total with taxes and fees
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 UMass

Hotel UMass

10/10 Excellent
"Everything was great. Nice pastries. So convenient. "
Ieva 2-night trip
Posted 1 day ago
Hotel UMass

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
59
Accommodation
110 Cottages
Lowest Price
$309
Highest Price
$1,765

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between $309 and $1,765 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 110 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!
How can I find cheap cottages in Western Massachusetts?
Expedia can help you easily locate cheap cottages in Western Massachusetts. To lock in your perfect stay in a few clicks, simply use our handy filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Western Massachusetts near my cottage?
The most important travel accessory for your Western Massachusetts trip is a well-organized itinerary! Titanic Museum, Springfield Armory and Springfield City Library are some of the well-known sights if you're heading to Springfield. West Springfield is also packed with wonderful attractions, such as Big E. Need more travel inspo? Find time for Eastern States Exposition and Olympia Ice Center too.

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