Search Western Massachusetts Cottage Rentals from CA $323

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Our top choices for Western Massachusetts cottages

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is CA $206
CA $477 total
includes taxes & fees
May 27 - May 28
Trainmaster's Inn - Caboose

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is CA $256
CA $401 total
includes taxes & fees
May 26 - May 27
Cabin & Sauna on Lake Monomonac near Mt. Monadnock

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (37 reviews)
"Great location, beautiful view completely relaxing "
United States
Carlos T.
The price is CA $203
CA $484 total
includes taxes & fees
May 25 - May 26
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is CA $257
CA $505 total
includes taxes & fees
May 31 - Jun 1
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
The price is CA $210
CA $564 total
includes taxes & fees
Jun 15 - Jun 16
Hiking Trails On-site: Cozy Falls Brook Cabin

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
The price is CA $186
CA $323 total
includes taxes & fees
May 24 - May 25
Brookside cottage near the mountains and outdoor recreation

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is CA $1,685
CA $3,173 total
includes taxes & fees
May 21 - May 22
Berkshires farm, 30+ guests, 50 acres

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is CA $269
CA $761 total
includes taxes & fees
Jun 15 - Jun 16
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat
3.0 star property
Windsor
The price is CA $471
CA $953 total
includes taxes & fees
May 24 - May 25
Spacious Yard w/ Gazebo: Charming Windsor Retreat
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

Find out more about Western Massachusetts

Western Massachusetts Cottages information

Number of reviews
51
Accommodation
115 Cottages
Lowest Price
CA $323
Highest Price
CA $3,173

Frequently asked questions

How much do cottages in Western Massachusetts cost?
Cottages in Western Massachusetts range between CA $323 and CA $3,173 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 115 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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